Co-reporter:Hon Eong Ho, Kazuaki Oniwa, Yoshinori Yamamoto, and Tienan Jin
Organic Letters 2016 Volume 18(Issue 10) pp:2487-2490
Publication Date(Web):May 6, 2016
DOI:10.1021/acs.orglett.6b01067
A novel intramolecular oxidative diamination of bis(2-aminophenyl)acetylene for the synthesis of the structurally intriguing π-conjugated polyheterocyclic scaffold, 5,10-dihydroindolo[3,2-b]indole (DHII), has been developed under Cu(hfacac)2/O2 oxidation systems. The structure design of bis(2-aminophenyl)acetylene bearing both N,N-dimethylamine and primary amine groups is crucial for constructing the corresponding DHII scaffold. Notably, an intermolecular N-methyl transfer from the nitrogen atom of N,N-dimethylamine to the primary amine takes place, which is a critical step for the successful implementation of the present annulation process.
Co-reporter:Kazuaki Oniwa, Hiromasa Kikuchi, Hidekazu Shimotani, Susumu Ikeda, Naoki Asao, Yoshinori Yamamoto, Katsumi Tanigaki and Tienan Jin
Chemical Communications 2016 vol. 52(Issue 26) pp:4800-4803
Publication Date(Web):03 Mar 2016
DOI:10.1039/C6CC00948D
Three new 2-positional pyrene end-capped oligothiophene co-oligomers, BPynT (n = 1, 2, 3), have been synthesized for application in organic field effect transistors (OFETs). BPy2T showed the highest hole mobility of 3.3 cm2 V−1 s−1 in a single crystal OFET and a good photoluminescence efficiency of 32% in the crystalline state. A green light emission was observed for the OFET based on a BPy2T single crystal.
Co-reporter:Kazuaki Oniwa, Hiromasa Kikuchi, Thangavel Kanagasekaran, Hidekazu Shimotani, Susumu Ikeda, Naoki Asao, Yoshinori Yamamoto, Katsumi Tanigaki and Tienan Jin
Chemical Communications 2016 vol. 52(Issue 27) pp:4926-4929
Publication Date(Web):04 Mar 2016
DOI:10.1039/C6CC01352J
Two new regiospecific biphenyl end-capped bithiazole co-oligomers, BP2Tz(in) and BP2Tz(out), have been synthesized for application in thin film field effect transistors (TFTs). BP2Tz(in) with a 2,2′-bithiazole central unit exhibits a field effect hole mobility as high as 3.5 cm2 V−1 s−1. Green light emission is demonstrated for highly balanced ambipoar TFTs based on both BP2Tz(in) and BP2Tz(out).
Co-reporter:Dr. Jian Zhao;Zhanqiang Xu;Dr. Kazuaki Oniwa; Naoki Asao; Yoshinori Yamamoto; Tienan Jin
Angewandte Chemie 2016 Volume 128( Issue 1) pp:267-271
Publication Date(Web):
DOI:10.1002/ange.201507794
Abstract
A novel FeCl3-mediated oxidative spirocyclization for construction of a new class of di-spirolinked π-conjugated molecules, dispiro[fluorene-9,5′-indeno[2,1-a]indene-10′,9′′-fluorene]s (DSFIIFs), has been reported. The combination of FeCl3 with FeO(OH) triggered an unprecedented double one-electron oxidation of difluorenylidene diarylethanes to afford the corresponding dispirocycles in high yields. The highest fluorescence quantum yield was up to 0.94 in solution. This protocol is also applicable to the synthesis of the non-spirolinked dihydroindenoindenes.
Co-reporter:Dr. Jian Zhao;Zhanqiang Xu;Dr. Kazuaki Oniwa; Naoki Asao; Yoshinori Yamamoto; Tienan Jin
Angewandte Chemie International Edition 2016 Volume 55( Issue 1) pp:259-263
Publication Date(Web):
DOI:10.1002/anie.201507794
Abstract
A novel FeCl3-mediated oxidative spirocyclization for construction of a new class of di-spirolinked π-conjugated molecules, dispiro[fluorene-9,5′-indeno[2,1-a]indene-10′,9′′-fluorene]s (DSFIIFs), has been reported. The combination of FeCl3 with FeO(OH) triggered an unprecedented double one-electron oxidation of difluorenylidene diarylethanes to afford the corresponding dispirocycles in high yields. The highest fluorescence quantum yield was up to 0.94 in solution. This protocol is also applicable to the synthesis of the non-spirolinked dihydroindenoindenes.
Co-reporter:Weili Si, Xuan Zhang, Naoki Asao, Yoshinori Yamamoto and Tienan Jin
Chemical Communications 2015 vol. 51(Issue 29) pp:6392-6394
Publication Date(Web):05 Mar 2015
DOI:10.1039/C5CC01534K
A new Ni-catalyzed direct 1,4-difunctionalization of [60]fullerene with various benzyl bromides has been developed. The use of a DMSO additive combined with a nickel catalyst is indispensable for the formation of 1,4-dibenzyl fullerenes with a variety of functional groups. The reaction proceeds through the formation of a fullerene monoradical species.
Co-reporter:Hon Eong Ho, Yoshifumi Ishikawa, Naoki Asao, Yoshinori Yamamoto and Tienan Jin
Chemical Communications 2015 vol. 51(Issue 64) pp:12764-12767
Publication Date(Web):01 Jul 2015
DOI:10.1039/C5CC04856G
We report for the first time that zero-valent nanoporous gold (AuNPore) is a robust and green heterogeneous catalyst for α-C–H functionalization of various tertiary amines. AuNPore combines with molecular oxygen at 80 °C or tert-butyl hydrogen peroxide at room temperature and catalyses the heterogeneous cross-dehydrogenative coupling (CDC) reaction efficiently to afford the corresponding C–C and C-heteroatom coupling products in good to excellent yields with excellent reusability.
Co-reporter:Jian Zhao, Naoki Asao, Yoshinori Yamamoto, Tienan Jin
Tetrahedron Letters 2015 Volume 56(Issue 23) pp:3133-3136
Publication Date(Web):3 June 2015
DOI:10.1016/j.tetlet.2014.12.023
A novel Pd-catalyzed cascade cyclization of o-alkynylarylbromides with dialkylalkynes for the construction of the multisubstituted dihydrocyclopenta[a]indene derivatives has been reported. The reaction proceeds efficiently through a four consecutive carbopalladations with alkyne and alkene moieties.
Co-reporter:Hua Jiang, Kazuaki Oniwa, Ashraful Islam, Jian Zhao, Liyuan Han, Ying-Ji Sun, Ming Bao, Naoki Asao, Yoshinori Yamamoto, Tienan Jin
Tetrahedron 2015 Volume 71(Issue 37) pp:6534-6540
Publication Date(Web):16 September 2015
DOI:10.1016/j.tet.2015.04.018
A new series of donor-π-acceptor organic dyes based on thieno[3,2-a]carbazole as a new donor moiety, designated as JH-dyes, has been synthesized for dye-sensitized solar cells (DSCs). The photophysical properties and DSC performances of JH-dyes have been characterized. Among the three JH-dyes, a high power conversion efficiency (η) of 8.04% with a short-circuit current (Jsc) of 14.08 mA cm−2 and an open-circuit voltage (Voc) of 0.78 V has been achieved for DSC based on JH03 bearing hexyl chains on the terthiophene π-linker. The electrochemical impedance spectra (EIS) and intensity-modulated photovoltage spectroscopy (IMVS) of JH-cells were measured to understand the effect of molecular structure on charge transfer process and electron life time.
Co-reporter:Hua Jiang;Dr. Giovanni Ferrara;Xuan Zhang;Kazuaki Oniwa;Dr. Ashraful Islam;Dr. Liyuan Han;Dr. Ying-Ji Sun;Ming Bao;Dr. Naoki Asao;Dr. Yoshinori Yamamoto;Dr. Tienan Jin
Chemistry - A European Journal 2015 Volume 21( Issue 10) pp:4065-4070
Publication Date(Web):
DOI:10.1002/chem.201405860
Abstract
A new triflic acid (TfOH)-mediated cascade cyclization of ortho-anisole-substituted aryldiynes is described for the construction of indeno[1,2-c]chromenes. The cascade cyclization proceeds through an unusual TfOH-induced alkyne-alkyne cyclization followed by nucleophilic attack of the methoxy group on the benzylidene cation, which is completely different to the cyclization of ortho-aniline- or ortho-thioanisole-substituted aryldiynes. A new class of organic dyes with the indeno[1,2-c]chromene framework as both donor and π-linker were synthesized. These compounds exhibit high photovoltaic performances in dye- sensitized solar cells (DSCs).
Co-reporter:Jian Zhao ; Naoki Asao ; Yoshinori Yamamoto
Journal of the American Chemical Society 2014 Volume 136(Issue 27) pp:9540-9543
Publication Date(Web):June 20, 2014
DOI:10.1021/ja503252k
We report a novel Pd-catalyzed alkyne-directed dual C–H activation of bis-biaryl alkynes, which produced important and useful products, 9,9′-bifluorenylidene (9,9′BF) derivatives, in high yields with a broad range of functional group compatibility. The combination of the PdCl2 catalyst with the MnO2 oxidant and PivOH additive is vital for realization of the present catalytic transformation. Mechanistic evidence suggests that this intramolecular arene/alkyne annulation may take place through unusual dual C–H activation followed by annulation with alkynes.
Co-reporter:Weili Si, Shirong Lu, Naoki Asao, Ming Bao, Yoshinori Yamamoto and Tienan Jin
Chemical Communications 2014 vol. 50(Issue 99) pp:15730-15732
Publication Date(Web):27 Oct 2014
DOI:10.1039/C4CC07780F
We have demonstrated that NBS is able to promote the oxidation of fullerene monoradicals to form 1,4-difunctional fullerenes. The singly bonded fullerene dimers were used as fullerene monoradical precursors, which produced various 1,4-fullerenes with a wide range of functional groups in good to high yields with high regioselectivity in terms of cosolvents and nucleophiles.
Co-reporter:Xuan Zhang, Weili Si, Ming Bao, Naoki Asao, Yoshinori Yamamoto, and Tienan Jin
Organic Letters 2014 Volume 16(Issue 18) pp:4830-4833
Publication Date(Web):September 9, 2014
DOI:10.1021/ol502317c
A Rh(III)-catalyzed highly efficient and regioselective functionalization of diverse C–H bonds of naphthylcarbamates for oxidative annulation with alkynes has been developed. The annulation with a neutral rhodium catalyst system proceeds through peri C–H bond functionalization of arylcarbamates to give benzoquinoline derivatives, while with a cationic rhodium catalyst system it proceeds through ortho C–H functionalization of arylcarbamates to furnish benzoindole derivatives.
Co-reporter:Hon Eong Ho, Naoki Asao, Yoshinori Yamamoto, and Tienan Jin
Organic Letters 2014 Volume 16(Issue 17) pp:4670-4673
Publication Date(Web):August 25, 2014
DOI:10.1021/ol502285s
We have demonstrated for the first time that carboxylic acids are able to catalyze the direct hydroboration of various terminal and internal alkynes with pinacolborane without using any metal catalysts. This unprecedented catalytic hydroboration exhibits a broad functional groups compatibility, giving the corresponding alkenyl diboronates and monoboronates in good to high yields with exclusive regio- and stereoselectivities.
Co-reporter:Weili Si, Shirong Lu, Ming Bao, Naoki Asao, Yoshinori Yamamoto, and Tienan Jin
Organic Letters 2014 Volume 16(Issue 2) pp:620-623
Publication Date(Web):December 30, 2013
DOI:10.1021/ol403573r
A novel and highly efficient Cu-catalyzed C–H amination of the monofunctionalized hydrofullerenes for the synthesis of 1,4-difunctional fullerenes has been reported. A new series of 1,4-fullerene derivatives having various monoamine addends were synthesized in good to high yields under mild reaction conditions. The controlled experiments revealed that the reaction proceeds through the formation of a fullerene monoradical as a key intermediate followed by coupling with an amine radical.
Co-reporter:Qiang Chen, Shinya Tanaka, Takeshi Fujita, Luyang Chen, Taketoshi Minato, Yoshifumi Ishikawa, Mingwei Chen, Naoki Asao, Yoshinori Yamamoto and Tienan Jin
Chemical Communications 2014 vol. 50(Issue 25) pp:3344-3346
Publication Date(Web):10 Feb 2014
DOI:10.1039/C3CC49524H
The nanoporous AuPd (AuPdNPore) alloy catalyst showed superior chemoselectivity and high catalytic activity for the direct 1,4-hydrosilylation of the conjugated cyclic enones with hydrosilane in comparison with the monometallic nanoporous Au and Pd catalysts. The enhanced catalytic properties of AuPdNPore arise mainly from the nanoporous structure and the synergistic effect of the AuPd alloy.
Co-reporter:Jian Zhao, Tienan Jin, Ashraful Islam, Eunsang Kwon, Md. Akhtaruzzaman, Naoki Asao, Liyuan Han, Khalid A. Alamry, Samia A. Kosa, Abdullah Mohamed Asiri, Yoshinori Yamamoto
Tetrahedron 2014 70(36) pp: 6211-6216
Publication Date(Web):
DOI:10.1016/j.tet.2014.01.001
Co-reporter:Dr. Tienan Jin;Dr. Jian Zhao;Dr. Naoki Asao;Dr. Yoshinori Yamamoto
Chemistry - A European Journal 2014 Volume 20( Issue 13) pp:3554-3576
Publication Date(Web):
DOI:10.1002/chem.201304640
Abstract
The progress of the metal-catalyzed annulation reactions toward construction of various π-conjugated polycyclic cores with high conjugation extension is described. This article gives a brief overview of various annulation reactions promoted by metal catalysts including CH bond functionalization, [2+2+2] cycloaddition, cascade processes, ring closing metathesis, electrophilic aromatization, and various cross-coupling reactions. A variety of conjugated polycycles with planar, bowl-shaped, and helical structures have been constructed in high efficiency and selectivity.
Co-reporter:Jian Zhao ; Kazuaki Oniwa ; Naoki Asao ; Yoshinori Yamamoto
Journal of the American Chemical Society 2013 Volume 135(Issue 28) pp:10222-10225
Publication Date(Web):June 28, 2013
DOI:10.1021/ja403382d
A novel and selective Pd-catalyzed cascade crossover-annulation of o-alkynylarylhalides and diarylacetylenes for the synthesis of dibenzo[a,e]pentalenes has been reported. Various arylacetylenes with a wide range of functional groups were tolerated, producing the corresponding multisubstituted dibenzopentalenes with the different substituents on the aromatic rings in good to high yields under the optimized reaction conditions. The reaction proceeds through a Pd-catalyzed cascade carbopalladation and C–H activation. The use of the combined DBU and CsOPiv bases is crucial for the successful implementation of the present cross-annulation.
Co-reporter:Kazuaki Oniwa, Thangavel Kanagasekaran, Tienan Jin, Md. Akhtaruzzaman, Yoshinori Yamamoto, Hiroyuki Tamura, Ikutaro Hamada, Hidekazu Shimotani, Naoki Asao, Susumu Ikeda and Katsumi Tanigaki
Journal of Materials Chemistry A 2013 vol. 1(Issue 26) pp:4163-4170
Publication Date(Web):29 Apr 2013
DOI:10.1039/C3TC30220B
We report the synthesis and characterization of two new furan-based biphenyl end-capped oligomers, 2-([1,1′-biphenyl]-4-yl)-5-(5-([1,1′-biphenyl]-4-yl)thiophen-2-yl)furan (BPFT) and 5,5′-di([1,1′-biphenyl]-4-yl)-2,2′-bifuran (BP2F) as candidate semiconductors for organic light-emitting field effect transistors (OLETs). Differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) showed the high thermostability of these furan-based semiconductors. X-Ray crystallography of single crystals grown by physical vapor transfer (PVT) method revealed a complicated herringbone packing of BPFT stacking with unusual flat and bent structures, which is different from that of BP2F and the bithiophene-based analogue 5,5′-di([1,1′-biphenyl]-4-yl)-2,2′-bithiophene (BP2T). BPFT single crystal showed a higher absolute quantum yield (51%) compared to that of BP2F and BP2T. Density Functional Theory (DFT) calculations showed that the different excitation energies between flat and bent structures led to the asymmetric transition dipoles in dark state of BPFT H-aggregates, which explains the highest PLQY of BPFT single crystal. Single crystal FET based on BPFT showed an ambipolar characteristic with high hole and electron mobilities, while single crystal FET based on BP2F exhibited p-type characteristic with a high hole mobility. Light emission was observed from the single-crystal FET based on BPFT.
Co-reporter:Mei Yan, Tienan Jin, Qiang Chen, Hon Eong Ho, Takeshi Fujita, Lu-Yang Chen, Ming Bao, Ming-Wei Chen, Naoki Asao, and Yoshinori Yamamoto
Organic Letters 2013 Volume 15(Issue 7) pp:1484-1487
Publication Date(Web):March 15, 2013
DOI:10.1021/ol400229z
For the first time, the highly efficient and regioselective hydrogenation of quinoline derivatives to 1,2,3,4-tetrahydroquinolines using unsupported nanoporous gold (AuNPore) as a catalyst and organosilane with water as a hydrogen source is reported. The AuNPore catalyst can be readily recovered and reused without any loss of catalytic activity.
Co-reporter:Shirong Lu, Tienan Jin, Takeshi Yasuda, Weili Si, Kazuaki Oniwa, Khalid A. Alamry, Samia A. Kosa, Abdullah Mohamed Asiri, Liyuan Han, and Yoshinori Yamamoto
Organic Letters 2013 Volume 15(Issue 22) pp:5674-5677
Publication Date(Web):November 1, 2013
DOI:10.1021/ol4026606
A series of novel monobenzyl-substituted deuteriofullerenes (BnDCs) were synthesized efficiently through Co-catalyzed selective monofunctionalization of C60. Bulk heterojunction solar cells, based on poly(3-hexylthiophene) as the donor and BnDCs as the acceptors, exhibited higher photovoltaic performances as compared to the corresponding protonated BnHCs devices.
Co-reporter:Qiang Chen, Jian Zhao, Yoshifumi Ishikawa, Naoki Asao, Yoshinori Yamamoto, and Tienan Jin
Organic Letters 2013 Volume 15(Issue 22) pp:5766-5769
Publication Date(Web):October 25, 2013
DOI:10.1021/ol4028013
A novel catalytic property of nanoporous gold for activation of bis(pinacolato)diboron has been reported that allows the direct diboration of alkynes to proceed sufficiently in a heterogeneous process. The experimental results revealed that the nanoporous gold catalyst is able to cleave the B–B bond of bis(pinacolato)diboron without using any additives.
Co-reporter:Shirong Lu, Weili Si, Ming Bao, Yoshinori Yamamoto, and Tienan Jin
Organic Letters 2013 Volume 15(Issue 15) pp:4030-4033
Publication Date(Web):July 23, 2013
DOI:10.1021/ol401876n
An efficient and highly selective Co-catalyzed radical cycloaddition of [60]fullerene with active dibromides for the synthesis of three-, five-, six-, and seven-membered carbocycle-fused fullerene monoadducts has been reported. The controlled experiments unambiguously disclosed that the reaction proceeds through the formation of a fullerene monoradical as a key intermediate.
Co-reporter:Shirong Lu, Tienan Jin, Takeshi Yasuda, Ashraful Islam, Md. Akhtaruzzaman, Liyuan Han, Khalid A. Alamry, Samia A. Kosa, Abdullah Mohamed Asiri, Yoshinori Yamamoto
Tetrahedron 2013 69(4) pp: 1302-1306
Publication Date(Web):
DOI:10.1016/j.tet.2012.11.099
Co-reporter:Mei Yan ; Tienan Jin ; Yoshifumi Ishikawa ; Taketoshi Minato ; Takeshi Fujita ; Lu-Yang Chen ; Ming Bao ; Naoki Asao ; Ming-Wei Chen ;Yoshinori Yamamoto
Journal of the American Chemical Society 2012 Volume 134(Issue 42) pp:17536-17542
Publication Date(Web):October 1, 2012
DOI:10.1021/ja3087592
We report for the first time the highly selective semihydrogenation of alkynes using the unsupported nanoporous gold (AuNPore) as a catalyst and organosilanes with water as a hydrogen source. Under the optimized reaction conditions, the present semihydrogenation of various terminal- and internal-alkynes affords the corresponding alkenes in high chemical yields and excellent Z-selectivity without any over-reduced alkanes. The use of DMF as solvent, which generates amines in situ, or pyridine as an additive is crucial to suppress the association of hydrogen atoms on AuNPore to form H2 gas, which is unable to reduce alkynes on the unsupported gold catalysts. The AuNPore catalyst can be readily recovered and reused without any loss of catalytic activity. In addition, the SEM and TEM characterization of nanoporosity show that the AuNPore catalyst has a bicontinuous 3D structure and a high density of atomic steps and kinks on ligament surfaces, which should be one of the important origins of catalytic activity.
Co-reporter:Fan Yang, Md. Akhtaruzzaman, Ashraful Islam, Tienan Jin, Ahmed El-Shafei, Chuanjiang Qin, Liyuan Han, Khalid A. Alamry, Samia A. Kosa, Mahmoud A. Hussein, Abdullah Mohamed Asiri and Yoshinori Yamamoto
Journal of Materials Chemistry A 2012 vol. 22(Issue 42) pp:22550-22557
Publication Date(Web):13 Sep 2012
DOI:10.1039/C2JM34363K
Four new donor–π–acceptor organic dyes (YF01–04), containing naphthalene-substituted amines as an electron donor and cyanoacrylic acid as an electron acceptor, were designed and synthesized, and their photophysical properties and dye-sensitized solar cells (DSCs) performances were characterized. Dyes YF02 and YF04, with 2,6-disubstituted naphthalene frameworks, were superior than their analog dyes YF03 and YF01, having 1,2-disubstituted naphthalene moiety, in incident-photo-to-current conversion efficiency (IPCE) and total solar-to-electric conversion efficiency (η). The DSCs based on YF02, comprised of diphenylamine moiety as the donor, produced the highest η of 5.29% compared to 4.03% of the analog dye YF04, which has pyrrolidine as the donor. Remarkably, a high open-circuit photovoltage (Voc) of 0.799–0.807 V was achieved in the cases of YF02–03, which have diphenylamine-donors. To better understand the structure–property relationship for DSCs application, molecular modelling was performed on YF01–04 and vertical electronic excitations were calculated using long-range corrected energy functional WB97XD and CAM-B3LYP at the basis set level DGDZVP, which were in excellent agreement with the experimental results. Moreover, the equilibrium molecular geometries of dyes YF01–04 were calculated at the density function theory (DFT) level using the hybrid energy functional B3LYP and basis set DGDZVP. The torsion angles (θ) between the naphthalene moiety and diphenylamine donor in YF02 and YF03 were more twisted than that of the pyrrolidine-donor dyes YF01 and YF04, precluding efficient intermolecular π–π charge transfer, which translated into high Voc. Compared to the reference dye TA-St-CA, which is based on diphenylamine as an electron donor linked to a phenyl ring, YF02 achieved higher Voc, which indicated that naphthalene substituted with diphenylamine is more efficient in retarding charge recombinations.
Co-reporter:Shirong Lu, Tienan Jin, Ming Bao, and Yoshinori Yamamoto
Organic Letters 2012 Volume 14(Issue 13) pp:3466-3469
Publication Date(Web):June 18, 2012
DOI:10.1021/ol301435m
Unprecedented, transition-metal-free NaOH-catalyzed homo- and cross-dimerizations of monofunctionalized hydrofullerenes are reported. Various single-bonded fullerene dimers were synthesized under mild reaction conditions with remarkably high yields. The use of a NaOH catalyst combined with tetrahydrofuran as a cosolvent under an air atmosphere is critical in achieving highly efficient catalytic dimerization.
Co-reporter:Shirong Lu, Tienan Jin, Ming Bao, Abdullah M. Asiri, Yoshinori Yamamoto
Tetrahedron Letters 2012 Volume 53(Issue 10) pp:1210-1213
Publication Date(Web):7 March 2012
DOI:10.1016/j.tetlet.2011.12.075
A new, efficient palladium-catalyzed bisfunctionalization of ethylidene malononitriles by addition of acetonitrile and allyl groups is developed for the construction of all-carbon quarternary and tertiary centers simultaneously. This methodology is successfully applied to the synthesis of unsymmetric 1,4-disubstituted C60.
Co-reporter:Giovanni Ferrara, Tienan Jin, Kazuaki Oniwa, Jian Zhao, Abdullah M. Asiri, Yoshinori Yamamoto
Tetrahedron Letters 2012 Volume 53(Issue 8) pp:914-918
Publication Date(Web):22 February 2012
DOI:10.1016/j.tetlet.2011.11.132
A new class of symmetric π-conjugated donor–acceptor–donor (D–A–D) materials, with aryl- or heteroaryl[a]annulated carbazole (AHA[a]C) moieties as the donors and with 2,1,3-benzothiadiazole (BT) as an acceptor, has been synthesized via NaAuCl4-catalyzed double cascade cyclization of arenyl tetraynes in ethanol in good to high yields. Photophysical and electrochemical properties of the new D–A–D materials were investigated.
Co-reporter:Giovanni Ferrara, Tienan Jin, Md. Akhtaruzzaman, Ashraful Islam, Liyuan Han, Hua Jiang, Yoshinori Yamamoto
Tetrahedron Letters 2012 Volume 53(Issue 15) pp:1946-1950
Publication Date(Web):11 April 2012
DOI:10.1016/j.tetlet.2012.02.007
A facile, efficient, and general synthetic method for iodo-substituted benzo[b]naphtho[2,1-d]thiophenes has been developed via a cascade cyclization of thioanisole-substituted aryldiynes using iodine. A new donor–π linker–acceptor (D–π–A) organic dye, G1, with the benzo[b]naphtho[2,1-d]thiophene moiety as an electron donor has been synthesized, and the performance of dye-sensitized solar cell based on G1 has been investigated.
Co-reporter:Dr. Tienan Jin;Mei Yan;Dr. Yoshinori Yamamoto
ChemCatChem 2012 Volume 4( Issue 9) pp:1217-1229
Publication Date(Web):
DOI:10.1002/cctc.201200193
Abstract
With increasing advances on nanotechnology, the nanostructured copper catalysts have attracted much attention in alkyne–azide click reaction in the last few years owing to their large surface area, tunable morphology and sustainable catalytic activities. Supported copper nanoparticles are most widely employed. The shape, size and dispersity of supported copper nanoparticles are highly controlled by the used supports, as these will determine the catalytic activity of the heterogeneous click reaction. On the other hand, nanoporous coppers with specific three-dimensional open pore network structure was reported most recently, which can be fabricated with a tunable ligament or pore size without any supports, exhibiting high catalytic activity and reusability. This Minireview describes the state of the art with respect to the fabrication and catalytic application of both supported copper nanoparticles and nanoporous copper in click reaction.
Co-reporter:Shirong Lu;Dr. Tienan Jin;Dr. Eunsang Kwon;Dr. Ming Bao;Dr. Yoshinori Yamamoto
Angewandte Chemie International Edition 2012 Volume 51( Issue 3) pp:802-806
Publication Date(Web):
DOI:10.1002/anie.201107505
Co-reporter:Fan Yang, Tienan Jin, Yoshinori Yamamoto
Tetrahedron 2012 68(26) pp: 5223-5228
Publication Date(Web):
DOI:10.1016/j.tet.2012.03.053
Co-reporter:Shirong Lu;Dr. Tienan Jin;Dr. Eunsang Kwon;Dr. Ming Bao;Dr. Yoshinori Yamamoto
Angewandte Chemie 2012 Volume 124( Issue 3) pp:826-830
Publication Date(Web):
DOI:10.1002/ange.201107505
Co-reporter:Shirong Lu ; Tienan Jin ; Ming Bao ;Yoshinori Yamamoto
Journal of the American Chemical Society 2011 Volume 133(Issue 32) pp:12842-12848
Publication Date(Web):July 11, 2011
DOI:10.1021/ja204982w
The Co-catalyzed hydroalkylation of C60 with reactive alkyl bromides 1 (RBr) in the presence of Mn reductant and H2O at ambient temperature gave the monoalkylated C60 (2) in good to high yields. The use of CoLn/Mn/H2O under Ar atmosphere is crucial for the success of the present transformation. The reaction most probably proceeds through the Co(0 or I) complex-promoted generation of a radical (R•) followed by addition to C60. This hydroalkylation method was applied to the synthesis of zinc porphyrin attached C60 (2l), dendrimer attached C60 (2m), and fullerene dimer (2n), which were not easily available through the previously known methods.
Co-reporter:Fan Yang, Tienan Jin, Ming Bao and Yoshinori Yamamoto
Chemical Communications 2011 vol. 47(Issue 15) pp:4541-4543
Publication Date(Web):09 Mar 2011
DOI:10.1039/C1CC10584A
A facile, efficient, and general synthetic method for 3,4-dihalofurans has been developed via the electrophilic iodocyclization of various 4-hydroxy-2-but-2-yn-1-ones. The use of MeOH as a solvent is crucial for the efficient chemoselective synthesis of the corresponding 3,4-dihalofurans.
Co-reporter:Fan Yang, Tienan Jin, Ming Bao and Yoshinori Yamamoto
Chemical Communications 2011 vol. 47(Issue 13) pp:4013-4015
Publication Date(Web):21 Feb 2011
DOI:10.1039/C0CC05442A
A facile, efficient, and general synthetic method for a wide range of 2,3-diiodinated 1,4-dihydrothiophenes and naphthalenes has been developed via the electrophilic iodocyclization of various aryl propargyl alcohols. The resulting product 2p can be used for the synthesis of a rubrene intermediate.
Co-reporter:Tienan Jin;Mei Yan;Menggenbateer;Taketoshi Minato;Ming Bao;Yoshinori Yamamoto
Advanced Synthesis & Catalysis 2011 Volume 353( Issue 17) pp:3095-3100
Publication Date(Web):
DOI:10.1002/adsc.201100760
Abstract
Nanoporous copper (CuNPore) catalysts with tunable nanoporosity were fabricated from Cu30Mn70 alloy by controlling the de-alloying temperature under free corrosion conditions. The tunable nanoporosity of CuNPore led to a significant enhancement of catalytic activity in click chemistry without using any supports and bases. Characterization of CuNPore surface, high reusability, leaching experiment, and formation of nanostructured copper acetylide revealed that the click reaction occurred at the catalyst surface.
Co-reporter:Fan Yang, Tienan Jin, Ming Bao, Yoshinori Yamamoto
Tetrahedron Letters 2011 Volume 52(Issue 8) pp:936-938
Publication Date(Web):23 February 2011
DOI:10.1016/j.tetlet.2010.12.075
A facile, efficient, and general synthetic method for the construction of 3,4-diiododihydrothiophenes has been developed via the electrophilic iodocyclization of various S-hydroxy-2-butynyl ethanethioates. Application of the resulting iodine-containing products in organic transformations has been investigated.
Co-reporter:Tienan Jin, Junichi Uchiyama, Masafumi Himuro, Yoshinori Yamamoto
Tetrahedron Letters 2011 Volume 52(Issue 17) pp:2069-2071
Publication Date(Web):27 April 2011
DOI:10.1016/j.tetlet.2010.10.094
A novel triflic acid-catalyzed cascade cyclization of arenyl 1,7-enynes through acetylene-cation cyclization followed by Friedel–Crafts reaction has been described. Various fused poly carbocycles can be obtained in good to high yields under mild reaction conditions.
Co-reporter:Fan Yang, Tienan Jin, Ming Bao, Yoshinori Yamamoto
Tetrahedron 2011 67(52) pp: 10147-10155
Publication Date(Web):
DOI:10.1016/j.tet.2011.08.084
Co-reporter:Menggenbateer, Meda Narsireddy, Giovanni Ferrara, Naoko Nishina, Tienan Jin, Yoshinori Yamamoto
Tetrahedron Letters 2010 Volume 51(Issue 35) pp:4627-4629
Publication Date(Web):1 September 2010
DOI:10.1016/j.tetlet.2010.06.125
AuBr3-catalyzed regiospecific intermolecular hydrothiolation of aromatic allenes and aromatic thiols afforded the corresponding dithioacetals in good yields at 0 °C in 5 min.
Co-reporter:Kazuaki Oniwa, Hiromasa Kikuchi, Hidekazu Shimotani, Susumu Ikeda, Naoki Asao, Yoshinori Yamamoto, Katsumi Tanigaki and Tienan Jin
Chemical Communications 2016 - vol. 52(Issue 26) pp:NaN4803-4803
Publication Date(Web):2016/03/03
DOI:10.1039/C6CC00948D
Three new 2-positional pyrene end-capped oligothiophene co-oligomers, BPynT (n = 1, 2, 3), have been synthesized for application in organic field effect transistors (OFETs). BPy2T showed the highest hole mobility of 3.3 cm2 V−1 s−1 in a single crystal OFET and a good photoluminescence efficiency of 32% in the crystalline state. A green light emission was observed for the OFET based on a BPy2T single crystal.
Co-reporter:Kazuaki Oniwa, Hiromasa Kikuchi, Thangavel Kanagasekaran, Hidekazu Shimotani, Susumu Ikeda, Naoki Asao, Yoshinori Yamamoto, Katsumi Tanigaki and Tienan Jin
Chemical Communications 2016 - vol. 52(Issue 27) pp:NaN4929-4929
Publication Date(Web):2016/03/04
DOI:10.1039/C6CC01352J
Two new regiospecific biphenyl end-capped bithiazole co-oligomers, BP2Tz(in) and BP2Tz(out), have been synthesized for application in thin film field effect transistors (TFTs). BP2Tz(in) with a 2,2′-bithiazole central unit exhibits a field effect hole mobility as high as 3.5 cm2 V−1 s−1. Green light emission is demonstrated for highly balanced ambipoar TFTs based on both BP2Tz(in) and BP2Tz(out).
Co-reporter:Qiang Chen, Shinya Tanaka, Takeshi Fujita, Luyang Chen, Taketoshi Minato, Yoshifumi Ishikawa, Mingwei Chen, Naoki Asao, Yoshinori Yamamoto and Tienan Jin
Chemical Communications 2014 - vol. 50(Issue 25) pp:NaN3346-3346
Publication Date(Web):2014/02/10
DOI:10.1039/C3CC49524H
The nanoporous AuPd (AuPdNPore) alloy catalyst showed superior chemoselectivity and high catalytic activity for the direct 1,4-hydrosilylation of the conjugated cyclic enones with hydrosilane in comparison with the monometallic nanoporous Au and Pd catalysts. The enhanced catalytic properties of AuPdNPore arise mainly from the nanoporous structure and the synergistic effect of the AuPd alloy.
Co-reporter:Weili Si, Xuan Zhang, Naoki Asao, Yoshinori Yamamoto and Tienan Jin
Chemical Communications 2015 - vol. 51(Issue 29) pp:NaN6394-6394
Publication Date(Web):2015/03/05
DOI:10.1039/C5CC01534K
A new Ni-catalyzed direct 1,4-difunctionalization of [60]fullerene with various benzyl bromides has been developed. The use of a DMSO additive combined with a nickel catalyst is indispensable for the formation of 1,4-dibenzyl fullerenes with a variety of functional groups. The reaction proceeds through the formation of a fullerene monoradical species.
Co-reporter:Fan Yang, Md. Akhtaruzzaman, Ashraful Islam, Tienan Jin, Ahmed El-Shafei, Chuanjiang Qin, Liyuan Han, Khalid A. Alamry, Samia A. Kosa, Mahmoud A. Hussein, Abdullah Mohamed Asiri and Yoshinori Yamamoto
Journal of Materials Chemistry A 2012 - vol. 22(Issue 42) pp:NaN22557-22557
Publication Date(Web):2012/09/13
DOI:10.1039/C2JM34363K
Four new donor–π–acceptor organic dyes (YF01–04), containing naphthalene-substituted amines as an electron donor and cyanoacrylic acid as an electron acceptor, were designed and synthesized, and their photophysical properties and dye-sensitized solar cells (DSCs) performances were characterized. Dyes YF02 and YF04, with 2,6-disubstituted naphthalene frameworks, were superior than their analog dyes YF03 and YF01, having 1,2-disubstituted naphthalene moiety, in incident-photo-to-current conversion efficiency (IPCE) and total solar-to-electric conversion efficiency (η). The DSCs based on YF02, comprised of diphenylamine moiety as the donor, produced the highest η of 5.29% compared to 4.03% of the analog dye YF04, which has pyrrolidine as the donor. Remarkably, a high open-circuit photovoltage (Voc) of 0.799–0.807 V was achieved in the cases of YF02–03, which have diphenylamine-donors. To better understand the structure–property relationship for DSCs application, molecular modelling was performed on YF01–04 and vertical electronic excitations were calculated using long-range corrected energy functional WB97XD and CAM-B3LYP at the basis set level DGDZVP, which were in excellent agreement with the experimental results. Moreover, the equilibrium molecular geometries of dyes YF01–04 were calculated at the density function theory (DFT) level using the hybrid energy functional B3LYP and basis set DGDZVP. The torsion angles (θ) between the naphthalene moiety and diphenylamine donor in YF02 and YF03 were more twisted than that of the pyrrolidine-donor dyes YF01 and YF04, precluding efficient intermolecular π–π charge transfer, which translated into high Voc. Compared to the reference dye TA-St-CA, which is based on diphenylamine as an electron donor linked to a phenyl ring, YF02 achieved higher Voc, which indicated that naphthalene substituted with diphenylamine is more efficient in retarding charge recombinations.
Co-reporter:Hon Eong Ho, Yoshifumi Ishikawa, Naoki Asao, Yoshinori Yamamoto and Tienan Jin
Chemical Communications 2015 - vol. 51(Issue 64) pp:NaN12767-12767
Publication Date(Web):2015/07/01
DOI:10.1039/C5CC04856G
We report for the first time that zero-valent nanoporous gold (AuNPore) is a robust and green heterogeneous catalyst for α-C–H functionalization of various tertiary amines. AuNPore combines with molecular oxygen at 80 °C or tert-butyl hydrogen peroxide at room temperature and catalyses the heterogeneous cross-dehydrogenative coupling (CDC) reaction efficiently to afford the corresponding C–C and C-heteroatom coupling products in good to excellent yields with excellent reusability.
Co-reporter:Jian Zhao, Kazuaki Oniwa, Ashraful Islam, Chuanjiang Qin, Naoki Asao, Liyuan Han, Yoshinori Yamamoto and Tienan Jin
Inorganic Chemistry Frontiers 2015 - vol. 2(Issue 3) pp:NaN258-258
Publication Date(Web):2015/01/20
DOI:10.1039/C4QO00285G
A new series of donor–π-acceptor organic K-dyes based on the thieno[2,3,a]carbazole moiety as a new electron donor, trithiophene as a π-linker and cyanoacrylic acid as an electron acceptor were designed and synthesized for achieving high performances in dye-sensitized solar cells (DSCs). The substituent effect and the molecular planarity for photophysical properties and DSC performances of K-dyes have been investigated, and the highest power conversion efficiency of 7.4% has been achieved. EIS and IMVS were employed to study the effect of the molecular structure on the charge transfer process and electron lifetime.
Co-reporter:Fan Yang, Tienan Jin, Ming Bao and Yoshinori Yamamoto
Chemical Communications 2011 - vol. 47(Issue 13) pp:NaN4015-4015
Publication Date(Web):2011/02/21
DOI:10.1039/C0CC05442A
A facile, efficient, and general synthetic method for a wide range of 2,3-diiodinated 1,4-dihydrothiophenes and naphthalenes has been developed via the electrophilic iodocyclization of various aryl propargyl alcohols. The resulting product 2p can be used for the synthesis of a rubrene intermediate.
Co-reporter:Fan Yang, Tienan Jin, Ming Bao and Yoshinori Yamamoto
Chemical Communications 2011 - vol. 47(Issue 15) pp:NaN4543-4543
Publication Date(Web):2011/03/09
DOI:10.1039/C1CC10584A
A facile, efficient, and general synthetic method for 3,4-dihalofurans has been developed via the electrophilic iodocyclization of various 4-hydroxy-2-but-2-yn-1-ones. The use of MeOH as a solvent is crucial for the efficient chemoselective synthesis of the corresponding 3,4-dihalofurans.
Co-reporter:Kazuaki Oniwa, Thangavel Kanagasekaran, Tienan Jin, Md. Akhtaruzzaman, Yoshinori Yamamoto, Hiroyuki Tamura, Ikutaro Hamada, Hidekazu Shimotani, Naoki Asao, Susumu Ikeda and Katsumi Tanigaki
Journal of Materials Chemistry A 2013 - vol. 1(Issue 26) pp:NaN4170-4170
Publication Date(Web):2013/04/29
DOI:10.1039/C3TC30220B
We report the synthesis and characterization of two new furan-based biphenyl end-capped oligomers, 2-([1,1′-biphenyl]-4-yl)-5-(5-([1,1′-biphenyl]-4-yl)thiophen-2-yl)furan (BPFT) and 5,5′-di([1,1′-biphenyl]-4-yl)-2,2′-bifuran (BP2F) as candidate semiconductors for organic light-emitting field effect transistors (OLETs). Differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) showed the high thermostability of these furan-based semiconductors. X-Ray crystallography of single crystals grown by physical vapor transfer (PVT) method revealed a complicated herringbone packing of BPFT stacking with unusual flat and bent structures, which is different from that of BP2F and the bithiophene-based analogue 5,5′-di([1,1′-biphenyl]-4-yl)-2,2′-bithiophene (BP2T). BPFT single crystal showed a higher absolute quantum yield (51%) compared to that of BP2F and BP2T. Density Functional Theory (DFT) calculations showed that the different excitation energies between flat and bent structures led to the asymmetric transition dipoles in dark state of BPFT H-aggregates, which explains the highest PLQY of BPFT single crystal. Single crystal FET based on BPFT showed an ambipolar characteristic with high hole and electron mobilities, while single crystal FET based on BP2F exhibited p-type characteristic with a high hole mobility. Light emission was observed from the single-crystal FET based on BPFT.
Co-reporter:Weili Si, Shirong Lu, Naoki Asao, Ming Bao, Yoshinori Yamamoto and Tienan Jin
Chemical Communications 2014 - vol. 50(Issue 99) pp:NaN15732-15732
Publication Date(Web):2014/10/27
DOI:10.1039/C4CC07780F
We have demonstrated that NBS is able to promote the oxidation of fullerene monoradicals to form 1,4-difunctional fullerenes. The singly bonded fullerene dimers were used as fullerene monoradical precursors, which produced various 1,4-fullerenes with a wide range of functional groups in good to high yields with high regioselectivity in terms of cosolvents and nucleophiles.
![10H-Thieno[2,3-a]carbazole, 10-[3,5-bis(1,1-dimethylethyl)-4-methoxyphenyl]-5-phenyl-](/data/chemimg/3740900/1839513-77-7.png)
![10H-Thieno[2,3-a]carbazole, 10-[3,5-bis(1,1-dimethylethyl)-4-methoxyphenyl]-5-phenyl-](/data/chemimg/3740900/1839513-77-7_b.png)
![10H-Thieno[2,3-a]carbazole, 10-ethyl-5-phenyl-](/data/chemimg/3740900/1839510-98-3.png)
![10H-Thieno[2,3-a]carbazole, 10-ethyl-5-phenyl-](/data/chemimg/3740900/1839510-98-3_b.png)
![Indeno[2,1-a]indene, 5,10-dihydro-2,7-dimethyl-5,5,10,10-tetrakis(4-methylphenyl)-](/data/chemimg/3740900/1820767-56-3.png)
![Indeno[2,1-a]indene, 5,10-dihydro-2,7-dimethyl-5,5,10,10-tetrakis(4-methylphenyl)-](/data/chemimg/3740900/1820767-56-3_b.png)
![Isoquinoline, 1,2,3,4-tetrahydro-2-[(4-methoxyphenyl)methyl]-1-(nitromethyl)-](/data/chemimg/3740900/1802172-47-9.png)
![Isoquinoline, 1,2,3,4-tetrahydro-2-[(4-methoxyphenyl)methyl]-1-(nitromethyl)-](/data/chemimg/3740900/1802172-47-9_b.png)
![Isoquinoline, 1,2,3,4-tetrahydro-1-(nitromethyl)-2-[4-(trifluoromethyl)phenyl]-](/data/chemimg/3740900/1801982-09-1.png)
![Isoquinoline, 1,2,3,4-tetrahydro-1-(nitromethyl)-2-[4-(trifluoromethyl)phenyl]-](/data/chemimg/3740900/1801982-09-1_b.png)
![Cyclopent[a]indene, 8,8a-dihydro-3-(4-methoxyphenyl)-1,2,8a-tripentyl-8-pentylidene-, (8E)-](/data/chemimg/3740900/1644434-53-6.png)
![Cyclopent[a]indene, 8,8a-dihydro-3-(4-methoxyphenyl)-1,2,8a-tripentyl-8-pentylidene-, (8E)-](/data/chemimg/3740900/1644434-53-6_b.png)
![Cyclopent[a]indene, 1,2,8a-triethyl-8-ethylidene-6-fluoro-8,8a-dihydro-3-(4-methoxyphenyl)-, (8E)-](/data/chemimg/3740900/1644434-52-5.png)
![Cyclopent[a]indene, 1,2,8a-triethyl-8-ethylidene-6-fluoro-8,8a-dihydro-3-(4-methoxyphenyl)-, (8E)-](/data/chemimg/3740900/1644434-52-5_b.png)
![Cyclopent[a]indene, 3-[1,1-biphenyl]-4-yl-1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-6-methyl-, (8E)-](/data/chemimg/3740900/1644434-51-4.png)
![Cyclopent[a]indene, 3-[1,1-biphenyl]-4-yl-1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-6-methyl-, (8E)-](/data/chemimg/3740900/1644434-51-4_b.png)
![Benzoic acid, 4-[(8Z)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]-, methyl ester](/data/chemimg/3740900/1644434-50-3.png)
![Benzoic acid, 4-[(8Z)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]-, methyl ester](/data/chemimg/3740900/1644434-50-3_b.png)
![Benzoic acid, 4-[(8E)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]-, methyl ester](/data/chemimg/3740900/1644434-49-0.png)
![Benzoic acid, 4-[(8E)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]-, methyl ester](/data/chemimg/3740900/1644434-49-0_b.png)
![Benzonitrile, 4-[(8Z)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]-](/data/chemimg/3740900/1644434-48-9.png)
![Benzonitrile, 4-[(8Z)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]-](/data/chemimg/3740900/1644434-48-9_b.png)
![Benzonitrile, 4-[(8E)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]-](/data/chemimg/3740900/1644434-47-8.png)
![Benzonitrile, 4-[(8E)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]-](/data/chemimg/3740900/1644434-47-8_b.png)
![Cyclopent[a]indene, 1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-3-(6-methoxy-2-naphthalenyl)-, (8E)-](/data/chemimg/3740900/1644434-46-7.png)
![Cyclopent[a]indene, 1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-3-(6-methoxy-2-naphthalenyl)-, (8E)-](/data/chemimg/3740900/1644434-46-7_b.png)
![Cyclopent[a]indene, 3-[1,1-biphenyl]-4-yl-1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-, (8E)-](/data/chemimg/3740900/1644434-45-6.png)
![Cyclopent[a]indene, 3-[1,1-biphenyl]-4-yl-1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-, (8E)-](/data/chemimg/3740900/1644434-45-6_b.png)
![Cyclopent[a]indene, 1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-3-phenyl-, (8E)-](/data/chemimg/3740900/1644434-44-5.png)
![Cyclopent[a]indene, 1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-3-phenyl-, (8E)-](/data/chemimg/3740900/1644434-44-5_b.png)
![Cyclopent[a]indene, 1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-3-(4-methylphenyl)-, (8E)-](/data/chemimg/3740900/1644434-43-4.png)
![Cyclopent[a]indene, 1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-3-(4-methylphenyl)-, (8E)-](/data/chemimg/3740900/1644434-43-4_b.png)
![1,3-Benzodioxole, 5-[(8E)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]-](/data/chemimg/3740900/1644434-42-3.png)
![1,3-Benzodioxole, 5-[(8E)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]-](/data/chemimg/3740900/1644434-42-3_b.png)
![Carbamic acid, N-methyl-N-[4-[(8Z)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]phenyl]-, 1,1-dimethylethyl ester](/data/chemimg/3740900/1644434-41-2.png)
![Carbamic acid, N-methyl-N-[4-[(8Z)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]phenyl]-, 1,1-dimethylethyl ester](/data/chemimg/3740900/1644434-41-2_b.png)
![Carbamic acid, N-methyl-N-[4-[(8E)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]phenyl]-, 1,1-dimethylethyl ester](/data/chemimg/3740900/1644434-40-1.png)
![Carbamic acid, N-methyl-N-[4-[(8E)-1,2,8a-triethyl-8-ethylidene-8,8a-dihydrocyclopent[a]inden-3-yl]phenyl]-, 1,1-dimethylethyl ester](/data/chemimg/3740900/1644434-40-1_b.png)
![Benzene, 2-bromo-4-fluoro-1-[2-(4-methoxyphenyl)ethynyl]-](/data/chemimg/3740900/1644434-39-8.png)
![Benzene, 2-bromo-4-fluoro-1-[2-(4-methoxyphenyl)ethynyl]-](/data/chemimg/3740900/1644434-39-8_b.png)
![1,1-Biphenyl, 4-[2-(2-bromo-4-methylphenyl)ethynyl]-](/data/chemimg/3740900/1644434-38-7.png)
![1,1-Biphenyl, 4-[2-(2-bromo-4-methylphenyl)ethynyl]-](/data/chemimg/3740900/1644434-38-7_b.png)
![1,3-Benzodioxole, 5-[2-(2-bromophenyl)ethynyl]-](/data/chemimg/3740900/1644434-37-6.png)
![1,3-Benzodioxole, 5-[2-(2-bromophenyl)ethynyl]-](/data/chemimg/3740900/1644434-37-6_b.png)
![Carbamic acid, N-[4-[2-(2-bromophenyl)ethynyl]phenyl]-N-methyl-, 1,1-dimethylethyl ester](/data/chemimg/3740900/1644434-36-5.png)
![Carbamic acid, N-[4-[2-(2-bromophenyl)ethynyl]phenyl]-N-methyl-, 1,1-dimethylethyl ester](/data/chemimg/3740900/1644434-36-5_b.png)
![Cyclopent[a]indene, 1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-3-(4-methoxyphenyl)-, (8Z)-](/data/chemimg/3740900/1644434-35-4.png)
![Cyclopent[a]indene, 1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-3-(4-methoxyphenyl)-, (8Z)-](/data/chemimg/3740900/1644434-35-4_b.png)
![Cyclopent[a]indene, 1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-3-(4-methoxyphenyl)-, (8E)-](/data/chemimg/3740900/1644434-34-3.png)
![Cyclopent[a]indene, 1,2,8a-triethyl-8-ethylidene-8,8a-dihydro-3-(4-methoxyphenyl)-, (8E)-](/data/chemimg/3740900/1644434-34-3_b.png)
![10H-Thieno[2,3-a]carbazole, 2-(5-iodo-2-thienyl)-10-octyl-5-phenyl-](/data/chemimg/3740900/1630976-76-9.png)
![10H-Thieno[2,3-a]carbazole, 2-(5-iodo-2-thienyl)-10-octyl-5-phenyl-](/data/chemimg/3740900/1630976-76-9_b.png)
![10H-Thieno[2,3-a]carbazole, 2-iodo-10-octyl-5-phenyl-](/data/chemimg/3740900/1630976-74-7.png)
![10H-Thieno[2,3-a]carbazole, 2-iodo-10-octyl-5-phenyl-](/data/chemimg/3740900/1630976-74-7_b.png)
![2-Propenoic acid, 3-[1-[(ethoxycarbonyl)amino]-2-naphthalenyl]-, ethyl ester, (2E)-](/data/chemimg/3740900/1627602-38-3.png)
![2-Propenoic acid, 3-[1-[(ethoxycarbonyl)amino]-2-naphthalenyl]-, ethyl ester, (2E)-](/data/chemimg/3740900/1627602-38-3_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-diphenyl-, 1,1-dimethylethyl ester](/data/chemimg/3740900/1627602-37-2.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-diphenyl-, 1,1-dimethylethyl ester](/data/chemimg/3740900/1627602-37-2_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-diphenyl-, methyl ester](/data/chemimg/3740900/1627602-36-1.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-diphenyl-, methyl ester](/data/chemimg/3740900/1627602-36-1_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 2-methyl-3-phenyl-, ethyl ester](/data/chemimg/3740900/1627602-35-0.png)
![1H-Benz[g]indole-1-carboxylic acid, 2-methyl-3-phenyl-, ethyl ester](/data/chemimg/3740900/1627602-35-0_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 3-methyl-2-phenyl-, ethyl ester](/data/chemimg/3740900/1627602-34-9.png)
![1H-Benz[g]indole-1-carboxylic acid, 3-methyl-2-phenyl-, ethyl ester](/data/chemimg/3740900/1627602-34-9_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-dipropyl-, ethyl ester](/data/chemimg/3740900/1627602-33-8.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-dipropyl-, ethyl ester](/data/chemimg/3740900/1627602-33-8_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-di-2-thienyl-, ethyl ester](/data/chemimg/3740900/1627602-32-7.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-di-2-thienyl-, ethyl ester](/data/chemimg/3740900/1627602-32-7_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-bis(4-methoxyphenyl)-, ethyl ester](/data/chemimg/3740900/1627602-31-6.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-bis(4-methoxyphenyl)-, ethyl ester](/data/chemimg/3740900/1627602-31-6_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-bis(4-chlorophenyl)-, ethyl ester](/data/chemimg/3740900/1627602-30-5.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-bis(4-chlorophenyl)-, ethyl ester](/data/chemimg/3740900/1627602-30-5_b.png)
![Indolo[7,6-g]indole-3,8-dicarboxylic acid, 1,2,6,7-tetraphenyl-, 3,8-diethyl ester](/data/chemimg/3740900/1627602-29-2.png)
![Indolo[7,6-g]indole-3,8-dicarboxylic acid, 1,2,6,7-tetraphenyl-, 3,8-diethyl ester](/data/chemimg/3740900/1627602-29-2_b.png)
![1H-Naphth[2,3-g]indole-1-carboxylic acid, 2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-28-1.png)
![1H-Naphth[2,3-g]indole-1-carboxylic acid, 2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-28-1_b.png)
![9H-Phenaleno[1,9-fg]indole-9-carboxylic acid, 7,8-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-27-0.png)
![9H-Phenaleno[1,9-fg]indole-9-carboxylic acid, 7,8-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-27-0_b.png)
![4H-Fluoreno[9,1-fg]indole-4-carboxylic acid, 5,6-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-26-9.png)
![4H-Fluoreno[9,1-fg]indole-4-carboxylic acid, 5,6-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-26-9_b.png)
![9H-Indeno[1,7-fg]indole-9-carboxylic acid, 4,5-dihydro-7,8-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-25-8.png)
![9H-Indeno[1,7-fg]indole-9-carboxylic acid, 4,5-dihydro-7,8-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-25-8_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 6-methoxy-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-24-7.png)
![1H-Benz[g]indole-1-carboxylic acid, 6-methoxy-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-24-7_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 5-methyl-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-23-6.png)
![1H-Benz[g]indole-1-carboxylic acid, 5-methyl-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-23-6_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 5-nitro-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-22-5.png)
![1H-Benz[g]indole-1-carboxylic acid, 5-nitro-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-22-5_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 5-bromo-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-21-4.png)
![1H-Benz[g]indole-1-carboxylic acid, 5-bromo-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-21-4_b.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-20-3.png)
![1H-Benz[g]indole-1-carboxylic acid, 2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-20-3_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-diphenyl-, 1,1-dimethylethyl ester](/data/chemimg/3740900/1627602-19-0.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-diphenyl-, 1,1-dimethylethyl ester](/data/chemimg/3740900/1627602-19-0_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-diphenyl-, methyl ester](/data/chemimg/3740900/1627602-18-9.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-diphenyl-, methyl ester](/data/chemimg/3740900/1627602-18-9_b.png)
![Ethanone, 1-(2,3-diphenyl-1H-benzo[de]quinolin-1-yl)-](/data/chemimg/3740900/1627602-17-8.png)
![Ethanone, 1-(2,3-diphenyl-1H-benzo[de]quinolin-1-yl)-](/data/chemimg/3740900/1627602-17-8_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2-methyl-3-phenyl-, ethyl ester](/data/chemimg/3740900/1627602-16-7.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2-methyl-3-phenyl-, ethyl ester](/data/chemimg/3740900/1627602-16-7_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 3-methyl-2-phenyl-, ethyl ester](/data/chemimg/3740900/1627602-15-6.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 3-methyl-2-phenyl-, ethyl ester](/data/chemimg/3740900/1627602-15-6_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-dipropyl-, ethyl ester](/data/chemimg/3740900/1627602-14-5.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-dipropyl-, ethyl ester](/data/chemimg/3740900/1627602-14-5_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-di-2-thienyl-, ethyl ester](/data/chemimg/3740900/1627602-13-4.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-di-2-thienyl-, ethyl ester](/data/chemimg/3740900/1627602-13-4_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-bis(4-methoxyphenyl)-, ethyl ester](/data/chemimg/3740900/1627602-12-3.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-bis(4-methoxyphenyl)-, ethyl ester](/data/chemimg/3740900/1627602-12-3_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-bis(4-chlorophenyl)-, ethyl ester](/data/chemimg/3740900/1627602-11-2.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-bis(4-chlorophenyl)-, ethyl ester](/data/chemimg/3740900/1627602-11-2_b.png)
![Benzo[lmn][2,7]phenanthroline-1,6-dicarboxylic acid, 2,3,7,8-tetraphenyl-, 1,6-diethyl ester](/data/chemimg/3740900/1627602-10-1.png)
![Benzo[lmn][2,7]phenanthroline-1,6-dicarboxylic acid, 2,3,7,8-tetraphenyl-, 1,6-diethyl ester](/data/chemimg/3740900/1627602-10-1_b.png)
![3H-Naphtho[1,2,3-de]quinoline-3-carboxylic acid, 1,2-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-09-8.png)
![3H-Naphtho[1,2,3-de]quinoline-3-carboxylic acid, 1,2-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-09-8_b.png)
![3H-Phenaleno[2,1,9-def]quinoline-3-carboxylic acid, 4,5-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-08-7.png)
![3H-Phenaleno[2,1,9-def]quinoline-3-carboxylic acid, 4,5-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-08-7_b.png)
![1H-Fluoreno[2,1,9-def]quinoline-1-carboxylic acid, 2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-07-6.png)
![1H-Fluoreno[2,1,9-def]quinoline-1-carboxylic acid, 2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-07-6_b.png)
![1H-Benzo[ij][2,7]naphthyridine-1-carboxylic acid, 2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-06-5.png)
![1H-Benzo[ij][2,7]naphthyridine-1-carboxylic acid, 2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-06-5_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 6-methoxy-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-05-4.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 6-methoxy-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-05-4_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 7-methyl-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-04-3.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 7-methyl-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-04-3_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 7-nitro-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-03-2.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 7-nitro-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-03-2_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 7-bromo-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-02-1.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 7-bromo-2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-02-1_b.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-01-0.png)
![1H-Benzo[de]quinoline-1-carboxylic acid, 2,3-diphenyl-, ethyl ester](/data/chemimg/3740900/1627602-01-0_b.png)
![1,3,2-Dioxaborolane, 2-[(1Z)-3-methoxy-1-(methoxymethyl)-1-propen-1-yl]-4,4,5,5-tetramethyl-](/data/chemimg/3740900/1622926-05-9.png)
![1,3,2-Dioxaborolane, 2-[(1Z)-3-methoxy-1-(methoxymethyl)-1-propen-1-yl]-4,4,5,5-tetramethyl-](/data/chemimg/3740900/1622926-05-9_b.png)
![1,3,2-Dioxaborolane, 2-[(1Z)-1,2-bis(4-fluorophenyl)ethenyl]-4,4,5,5-tetramethyl-](/data/chemimg/3740900/1622926-04-8.png)
![1,3,2-Dioxaborolane, 2-[(1Z)-1,2-bis(4-fluorophenyl)ethenyl]-4,4,5,5-tetramethyl-](/data/chemimg/3740900/1622926-04-8_b.png)
![2H-Pyran, 2-[[3,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propen-1-yl]oxy]tetrahydro-](/data/chemimg/3740900/1622926-01-5.png)
![2H-Pyran, 2-[[3,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propen-1-yl]oxy]tetrahydro-](/data/chemimg/3740900/1622926-01-5_b.png)
![1,3,2-Dioxaborolane, 2-(2-[1,1-biphenyl]-4-ylethynyl)-4,4,5,5-tetramethyl-](/data/chemimg/3740900/1622925-88-5.png)
![1,3,2-Dioxaborolane, 2-(2-[1,1-biphenyl]-4-ylethynyl)-4,4,5,5-tetramethyl-](/data/chemimg/3740900/1622925-88-5_b.png)
![1,3,2-Dioxaborolane, 2-[2-(4-butylphenyl)ethynyl]-4,4,5,5-tetramethyl-](/data/chemimg/3740900/1622925-87-4.png)
![1,3,2-Dioxaborolane, 2-[2-(4-butylphenyl)ethynyl]-4,4,5,5-tetramethyl-](/data/chemimg/3740900/1622925-87-4_b.png)
![1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(3-methylphenyl)ethynyl]-](/data/chemimg/3740900/1622925-86-3.png)
![1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(3-methylphenyl)ethynyl]-](/data/chemimg/3740900/1622925-86-3_b.png)
![2-Propenoic acid, 2-cyano-3-[5-[5-(10-octyl-5-phenyl-10H-thieno[2,3-a]carbazol-2-yl)-2-thienyl]-2-furanyl]-, (2E)-](/data/chemimg/3740900/1621457-07-5.png)
![2-Propenoic acid, 2-cyano-3-[5-[5-(10-octyl-5-phenyl-10H-thieno[2,3-a]carbazol-2-yl)-2-thienyl]-2-furanyl]-, (2E)-](/data/chemimg/3740900/1621457-07-5_b.png)
![2-Furancarboxaldehyde, 5-[5-(10-octyl-5-phenyl-10H-thieno[2,3-a]carbazol-2-yl)-2-thienyl]-](/data/chemimg/3740800/1621457-05-3.png)
![2-Furancarboxaldehyde, 5-[5-(10-octyl-5-phenyl-10H-thieno[2,3-a]carbazol-2-yl)-2-thienyl]-](/data/chemimg/3740800/1621457-05-3_b.png)
![10H-Thieno[2,3-a]carbazole, 10-octyl-5-phenyl-2-(2-thienyl)-](/data/chemimg/3740800/1621457-03-1.png)
![10H-Thieno[2,3-a]carbazole, 10-octyl-5-phenyl-2-(2-thienyl)-](/data/chemimg/3740800/1621457-03-1_b.png)
![Benzenamine, N-octyl-2-[2-[3-(2-phenylethynyl)-2-thienyl]ethynyl]-](/data/chemimg/3740800/1621457-01-9.png)
![Benzenamine, N-octyl-2-[2-[3-(2-phenylethynyl)-2-thienyl]ethynyl]-](/data/chemimg/3740800/1621457-01-9_b.png)
![Benzofuran, 2-[2-(2-[1,1-biphenyl]-2-ylethynyl)phenyl]-](/data/chemimg/3740800/1616754-89-2.png)
![Benzofuran, 2-[2-(2-[1,1-biphenyl]-2-ylethynyl)phenyl]-](/data/chemimg/3740800/1616754-89-2_b.png)
![Benzo[b]thiophene, 2-[2-(2-[1,1-biphenyl]-2-ylethynyl)phenyl]-](/data/chemimg/3740800/1616754-88-1.png)
![Benzo[b]thiophene, 2-[2-(2-[1,1-biphenyl]-2-ylethynyl)phenyl]-](/data/chemimg/3740800/1616754-88-1_b.png)
![Naphthalene, 2-[2-(2-[1,1-biphenyl]-2-ylethynyl)phenyl]-](/data/chemimg/3740800/1616754-87-0.png)
![Naphthalene, 2-[2-(2-[1,1-biphenyl]-2-ylethynyl)phenyl]-](/data/chemimg/3740800/1616754-87-0_b.png)
![1,1-Biphenyl, 2-(2-[1,1-biphenyl]-2-ylethynyl)-5-methyl-](/data/chemimg/3740800/1616754-86-9.png)
![1,1-Biphenyl, 2-(2-[1,1-biphenyl]-2-ylethynyl)-5-methyl-](/data/chemimg/3740800/1616754-86-9_b.png)
![1,1-Biphenyl, 2-(2-[1,1-biphenyl]-2-ylethynyl)-3-methyl-](/data/chemimg/3740800/1616754-85-8.png)
![1,1-Biphenyl, 2-(2-[1,1-biphenyl]-2-ylethynyl)-3-methyl-](/data/chemimg/3740800/1616754-85-8_b.png)
![1,1-Biphenyl, 2-(2-[1,1-biphenyl]-2-ylethynyl)-4-methyl-](/data/chemimg/3740800/1616754-83-6.png)
![1,1-Biphenyl, 2-(2-[1,1-biphenyl]-2-ylethynyl)-4-methyl-](/data/chemimg/3740800/1616754-83-6_b.png)
![[1,1-Biphenyl]-4-amine, 2-(2-[1,1-biphenyl]-2-ylethynyl)-N,N-diphenyl-](/data/chemimg/3740800/1616754-82-5.png)
![[1,1-Biphenyl]-4-amine, 2-(2-[1,1-biphenyl]-2-ylethynyl)-N,N-diphenyl-](/data/chemimg/3740800/1616754-82-5_b.png)
![1,1-Biphenyl, 2-(2-[1,1-biphenyl]-2-ylethynyl)-4-methoxy-](/data/chemimg/3740800/1616754-81-4.png)
![1,1-Biphenyl, 2-(2-[1,1-biphenyl]-2-ylethynyl)-4-methoxy-](/data/chemimg/3740800/1616754-81-4_b.png)
![1,1-Biphenyl, 2-(2-[1,1-biphenyl]-2-ylethynyl)-4-fluoro-](/data/chemimg/3740800/1616754-80-3.png)
![1,1-Biphenyl, 2-(2-[1,1-biphenyl]-2-ylethynyl)-4-fluoro-](/data/chemimg/3740800/1616754-80-3_b.png)
![[1,1-Biphenyl]-4-carboxylic acid, 2-(2-[1,1-biphenyl]-2-ylethynyl)-, methyl ester](/data/chemimg/3740800/1616754-79-0.png)
![[1,1-Biphenyl]-4-carboxylic acid, 2-(2-[1,1-biphenyl]-2-ylethynyl)-, methyl ester](/data/chemimg/3740800/1616754-79-0_b.png)
![[1,1-Biphenyl]-4-carboxaldehyde, 2-(2-[1,1-biphenyl]-2-ylethynyl)-](/data/chemimg/3740800/1616754-78-9.png)
![[1,1-Biphenyl]-4-carboxaldehyde, 2-(2-[1,1-biphenyl]-2-ylethynyl)-](/data/chemimg/3740800/1616754-78-9_b.png)
![9H-Fluorene, 2-(trifluoromethyl)-9-[2-(trifluoromethyl)-9H-fluoren-9-ylidene]-, (9E)-](/data/chemimg/3740800/1616754-76-7.png)
![9H-Fluorene, 2-(trifluoromethyl)-9-[2-(trifluoromethyl)-9H-fluoren-9-ylidene]-, (9E)-](/data/chemimg/3740800/1616754-76-7_b.png)
![9H-Fluorene, 2-(trifluoromethyl)-9-[2-(trifluoromethyl)-9H-fluoren-9-ylidene]-, (9Z)-](/data/chemimg/3740800/1616754-75-6.png)
![9H-Fluorene, 2-(trifluoromethyl)-9-[2-(trifluoromethyl)-9H-fluoren-9-ylidene]-, (9Z)-](/data/chemimg/3740800/1616754-75-6_b.png)
![10H-Benz[b]indeno[2,1-d]furan, 10-(9H-fluoren-9-ylidene)-4b,9b-dihydro-](/data/chemimg/3740800/1616754-73-4.png)
![10H-Benz[b]indeno[2,1-d]furan, 10-(9H-fluoren-9-ylidene)-4b,9b-dihydro-](/data/chemimg/3740800/1616754-73-4_b.png)
![10H-Benz[b]indeno[2,1-d]thiophene, 10-(9H-fluoren-9-ylidene)-4b,9b-dihydro-](/data/chemimg/3740800/1616754-72-3.png)
![10H-Benz[b]indeno[2,1-d]thiophene, 10-(9H-fluoren-9-ylidene)-4b,9b-dihydro-](/data/chemimg/3740800/1616754-72-3_b.png)
![Ethanone, 1-(2,3-diphenyl-1H-benz[g]indol-1-yl)-](/data/chemimg/3740800/1610681-58-7.png)
![Ethanone, 1-(2,3-diphenyl-1H-benz[g]indol-1-yl)-](/data/chemimg/3740800/1610681-58-7_b.png)
![1,3,2-Dioxaborolane, 2-[(1Z)-1,2-di-2-thienylethenyl]-4,4,5,5-tetramethyl-](/data/chemimg/3740800/1582799-98-1.png)
![1,3,2-Dioxaborolane, 2-[(1Z)-1,2-di-2-thienylethenyl]-4,4,5,5-tetramethyl-](/data/chemimg/3740800/1582799-98-1_b.png)
![Cyclohexene, 3,5-dimethyl-1-[(triethylsilyl)oxy]-, (3R,5R)-rel-](/data/chemimg/3740800/1575688-53-7.png)
![Cyclohexene, 3,5-dimethyl-1-[(triethylsilyl)oxy]-, (3R,5R)-rel-](/data/chemimg/3740800/1575688-53-7_b.png)
![Cyclohexene, 3,5-dimethyl-1-[(triethylsilyl)oxy]-, (3R,5S)-rel-](/data/chemimg/3740800/1575688-52-6.png)
![Cyclohexene, 3,5-dimethyl-1-[(triethylsilyl)oxy]-, (3R,5S)-rel-](/data/chemimg/3740800/1575688-52-6_b.png)
![Cyclohexene, 5-methyl-1-[(triethylsilyl)oxy]-](/data/chemimg/3740800/1575688-49-1.png)
![Cyclohexene, 5-methyl-1-[(triethylsilyl)oxy]-](/data/chemimg/3740800/1575688-49-1_b.png)
![1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(1-naphthalenyl)ethynyl]-](/data/chemimg/3740800/1418300-42-1.png)
![1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(1-naphthalenyl)ethynyl]-](/data/chemimg/3740800/1418300-42-1_b.png)
![Naphthalene, 2-[2-(2-bromophenyl)ethynyl]-6-methoxy-](/data/chemimg/3740800/1396301-36-2.png)
![Naphthalene, 2-[2-(2-bromophenyl)ethynyl]-6-methoxy-](/data/chemimg/3740800/1396301-36-2_b.png)
![11H-Benzo[a]fluorene, 11-(9H-fluoren-9-ylidene)-](/data/chemimg/3740800/1353012-53-9.png)
![11H-Benzo[a]fluorene, 11-(9H-fluoren-9-ylidene)-](/data/chemimg/3740800/1353012-53-9_b.png)
![Benzoic acid, 4-[2-(2-bromophenyl)ethynyl]-, methyl ester](/data/chemimg/3740800/1192159-83-3.png)
![Benzoic acid, 4-[2-(2-bromophenyl)ethynyl]-, methyl ester](/data/chemimg/3740800/1192159-83-3_b.png)
![1,1-Biphenyl, 2-[2-[4-(trifluoromethyl)phenyl]ethynyl]-](/data/chemimg/3740800/1192052-59-7.png)
![1,1-Biphenyl, 2-[2-[4-(trifluoromethyl)phenyl]ethynyl]-](/data/chemimg/3740800/1192052-59-7_b.png)
![1,1-Biphenyl, 2-[2-(4-butylphenyl)ethynyl]-](/data/chemimg/3740800/1097205-84-9.png)
![1,1-Biphenyl, 2-[2-(4-butylphenyl)ethynyl]-](/data/chemimg/3740800/1097205-84-9_b.png)
![2H-Pyran, tetrahydro-2-[[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propyn-1-yl]oxy]-](/data/chemimg/3740800/1068163-32-5.png)
![2H-Pyran, tetrahydro-2-[[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propyn-1-yl]oxy]-](/data/chemimg/3740800/1068163-32-5_b.png)
![Isoquinoline, 1,2,3,4-tetrahydro-2-[4-(trifluoromethyl)phenyl]-](/data/chemimg/3740800/1057277-76-5.png)
![Isoquinoline, 1,2,3,4-tetrahydro-2-[4-(trifluoromethyl)phenyl]-](/data/chemimg/3740800/1057277-76-5_b.png)
![Benzonitrile, 4-[2-(2-bromophenyl)ethynyl]-](/data/chemimg/3740800/1021176-20-4.png)
![Benzonitrile, 4-[2-(2-bromophenyl)ethynyl]-](/data/chemimg/3740800/1021176-20-4_b.png)
![1,3,2-Dioxaborolane, 2-[2-(1-cyclohexen-1-yl)ethynyl]-4,4,5,5-tetramethyl-](/data/chemimg/3740800/1016547-00-4.png)
![1,3,2-Dioxaborolane, 2-[2-(1-cyclohexen-1-yl)ethynyl]-4,4,5,5-tetramethyl-](/data/chemimg/3740800/1016547-00-4_b.png)
![11H-Benzo[b]fluorene, 11-(9H-fluoren-9-ylidene)-](/data/chemimg/3740800/942226-24-6.png)
![11H-Benzo[b]fluorene, 11-(9H-fluoren-9-ylidene)-](/data/chemimg/3740800/942226-24-6_b.png)
![1,3,2-Dioxaborolane, 2-[(1E)-2-[1,1-biphenyl]-4-ylethenyl]-4,4,5,5-tetramethyl-](/data/chemimg/3740800/941666-88-2.png)
![1,3,2-Dioxaborolane, 2-[(1E)-2-[1,1-biphenyl]-4-ylethenyl]-4,4,5,5-tetramethyl-](/data/chemimg/3740800/941666-88-2_b.png)
![1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(2-methylphenyl)ethynyl]-](/data/chemimg/3740800/872356-94-0.png)
![1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(2-methylphenyl)ethynyl]-](/data/chemimg/3740800/872356-94-0_b.png)
![1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(4-methylphenyl)ethynyl]-](/data/chemimg/3740800/872356-93-9.png)
![1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(4-methylphenyl)ethynyl]-](/data/chemimg/3740800/872356-93-9_b.png)
![Benzene, 1-[1-[bis(4-methylphenyl)methylene]-2,3,3-tris(4-methylphenyl)-2-propen-1-yl]-4-methyl-](/data/chemimg/3740800/801218-86-0.png)
![Benzene, 1-[1-[bis(4-methylphenyl)methylene]-2,3,3-tris(4-methylphenyl)-2-propen-1-yl]-4-methyl-](/data/chemimg/3740800/801218-86-0_b.png)
![Benzenamine, 2-[(2-aminophenyl)ethynyl]-N,N-dimethyl-](http://img.cochemist.com/ccimg/736200/736184-67-1.png)
![Benzenamine, 2-[(2-aminophenyl)ethynyl]-N,N-dimethyl-](http://img.cochemist.com/ccimg/736200/736184-67-1_b.png)
![BENZOIC ACID, 4-([1,1'-BIPHENYL]-2-YLETHYNYL)-, ETHYL ESTER](http://img.cochemist.com/ccimg/725300/725213-47-8.png)
![BENZOIC ACID, 4-([1,1'-BIPHENYL]-2-YLETHYNYL)-, ETHYL ESTER](http://img.cochemist.com/ccimg/725300/725213-47-8_b.png)
![1,1'-BIPHENYL, 2-[(4-METHOXYPHENYL)ETHYNYL]-](http://img.cochemist.com/ccimg/725300/725213-45-6.png)
![1,1'-BIPHENYL, 2-[(4-METHOXYPHENYL)ETHYNYL]-](http://img.cochemist.com/ccimg/725300/725213-45-6_b.png)
![1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(2-thienyl)ethynyl]-](/data/chemimg/3740800/634196-64-8.png)
![1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(2-thienyl)ethynyl]-](/data/chemimg/3740800/634196-64-8_b.png)
![Silane, [(4,4-dimethyl-1-cyclohexen-1-yl)oxy]triethyl-](http://img.cochemist.com/ccimg/496900/496862-77-2.png)
![Silane, [(4,4-dimethyl-1-cyclohexen-1-yl)oxy]triethyl-](http://img.cochemist.com/ccimg/496900/496862-77-2_b.png)
![1,1-Biphenyl, 4-[2-(2-bromophenyl)ethynyl]-](/data/chemimg/3740800/383191-51-3.png)
![1,1-Biphenyl, 4-[2-(2-bromophenyl)ethynyl]-](/data/chemimg/3740800/383191-51-3_b.png)
![Benzoic acid, 4-[(1E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]-, methyl ester](/data/chemimg/3740800/223919-55-9.png)
![Benzoic acid, 4-[(1E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]-, methyl ester](/data/chemimg/3740800/223919-55-9_b.png)
![Cycloheptene, 1-[(triethylsilyl)oxy]-](/data/chemimg/3740800/220800-76-0.png)
![Cycloheptene, 1-[(triethylsilyl)oxy]-](/data/chemimg/3740800/220800-76-0_b.png)
![Thiazole, 2-[1,1'-biphenyl]-4-yl-](http://img.cochemist.com/ccimg/199300/199296-86-1.png)
![Thiazole, 2-[1,1'-biphenyl]-4-yl-](http://img.cochemist.com/ccimg/199300/199296-86-1_b.png)
![Isoquinoline, 1,2,3,4-tetrahydro-2-[(4-methoxyphenyl)methyl]-](http://img.cochemist.com/ccimg/173100/173034-82-7.png)
![Isoquinoline, 1,2,3,4-tetrahydro-2-[(4-methoxyphenyl)methyl]-](http://img.cochemist.com/ccimg/173100/173034-82-7_b.png)
![1,3,2-Dioxaborolane, 2-[(1E)-2-cyclohexylethenyl]-4,4,5,5-tetramethyl-](http://img.cochemist.com/ccimg/172600/172512-85-5.png)
![1,3,2-Dioxaborolane, 2-[(1E)-2-cyclohexylethenyl]-4,4,5,5-tetramethyl-](http://img.cochemist.com/ccimg/172600/172512-85-5_b.png)
![Silane, triethyl[(2-methyl-1-cyclopenten-1-yl)oxy]-](http://img.cochemist.com/ccimg/148700/148678-75-5.png)
![Silane, triethyl[(2-methyl-1-cyclopenten-1-yl)oxy]-](http://img.cochemist.com/ccimg/148700/148678-75-5_b.png)
![1H-Benz[g]indole, 2,3-diphenyl-](/data/chemimg/3740700/116999-94-1.png)
![1H-Benz[g]indole, 2,3-diphenyl-](/data/chemimg/3740700/116999-94-1_b.png)
![Indeno[2,1-a]indene, 5,10-dihydro-5,5,10,10-tetraphenyl-](http://img.cochemist.com/ccimg/91900/91861-70-0.png)
![Indeno[2,1-a]indene, 5,10-dihydro-5,5,10,10-tetraphenyl-](http://img.cochemist.com/ccimg/91900/91861-70-0_b.png)
![Phosphonic acid, P-[[methyl(4-methylphenyl)amino]methyl]-, diethyl ester](/data/chemimg/3740700/80311-84-8.png)
![Phosphonic acid, P-[[methyl(4-methylphenyl)amino]methyl]-, diethyl ester](/data/chemimg/3740700/80311-84-8_b.png)
![Indolo[3,2-b]indole, 5,10-diethyl-5,10-dihydro-](http://img.cochemist.com/ccimg/80300/80243-03-4.png)
![Indolo[3,2-b]indole, 5,10-diethyl-5,10-dihydro-](http://img.cochemist.com/ccimg/80300/80243-03-4_b.png)
![Benzene, 1-bromo-2-[2-(4-methylphenyl)ethynyl]-](/data/chemimg/3740700/38175-73-4.png)
![Benzene, 1-bromo-2-[2-(4-methylphenyl)ethynyl]-](/data/chemimg/3740700/38175-73-4_b.png)
![Silane, triethyl[(3-methyl-1-cyclohexen-1-yl)oxy]-](http://img.cochemist.com/ccimg/18500/18407-91-5.png)
![Silane, triethyl[(3-methyl-1-cyclohexen-1-yl)oxy]-](http://img.cochemist.com/ccimg/18500/18407-91-5_b.png)
![Bis[(pentamethylcyclopentadienyl)dichloro-rhodium]](http://img.cochemist.com/ccimg/12400/12354-85-7.png)
![Bis[(pentamethylcyclopentadienyl)dichloro-rhodium]](http://img.cochemist.com/ccimg/12400/12354-85-7_b.png)
![3-[(2E)-3-(4-bromophenyl)prop-2-enoyl]-4,6-dimethylpyridin-2(1H)-one](http://img.cochemist.com/ccimg/5300/5255-68-5.png)
![3-[(2E)-3-(4-bromophenyl)prop-2-enoyl]-4,6-dimethylpyridin-2(1H)-one](http://img.cochemist.com/ccimg/5300/5255-68-5_b.png)
![Cyclopentene, 1-[(triethylsilyl)oxy]-](/data/chemimg/3740700/3931-87-1.png)
![Cyclopentene, 1-[(triethylsilyl)oxy]-](/data/chemimg/3740700/3931-87-1_b.png)
![10H-Thieno[2,3-a]carbazole, 10-octyl-5-phenyl-](/data/chemimg/3740700/1621457-02-0.png)
![10H-Thieno[2,3-a]carbazole, 10-octyl-5-phenyl-](/data/chemimg/3740700/1621457-02-0_b.png)
