Yu Peng

A Series of Fluorescent and Colorimetric Chemodosimeters for Selective Recognition of Cyanide Based on the FRET Mechanism

Co-reporter:Ying-Xi Hua, Yongliang Shao, Ya-Wen Wang, and Yu Peng

The Journal of Organic Chemistry June 16, 2017 Volume 82(Issue 12) pp:6259-6259

Publication Date(Web):May 26, 2017

DOI:10.1021/acs.joc.7b00850

A series of fluorescence “turn-on” probes (PY, AN, NA, B1, and B2) have been developed and successfully applied to detect cyanide anions based on the Michael addition reaction and FRET mechanism. These probes demonstrated good selectivity, high sensitivity, and very fast recognition for CN–. In particular, the fluorescence response of probe NA finished within 3 s. Low limits of detection (down to 63 nM) are also obtained in these probes with remarkable fluorescence enhancement factors. In addition, fluorescence colors of these probes turned to blue, yellow, or orange upon sensing CN–. In UV–vis mode, all of them showed ratiometric response for CN–. 1H NMR titration experiments and TDDFT calculations were taken to verify the mechanism of the specific reaction and fluorescence properties of the corresponding compounds. Moreover, silica gel plates with these probes were also fabricated and utilized to detect cyanide.

Fluorescein-Based Chromogenic and Ratiometric Fluorescence Probe for Highly Selective Detection of Cysteine and Its Application in Bioimaging

Co-reporter:Zhen-Hai Fu, Xiao Han, Yongliang Shao, Jianguo Fang, Zhi-Hong Zhang, Ya-Wen Wang, and Yu Peng

Analytical Chemistry February 7, 2017 Volume 89(Issue 3) pp:

Publication Date(Web):December 23, 2016

DOI:10.1021/acs.analchem.6b04431

A dual mode fluorescent probe, which is based on an integration of fluorescein and coumarin fluorophores, was developed for the discrimination of Cys from Hcy and GSH. This probe (2) shows the advantage of quick reaction (5 min) with Cys, resulting in a strong fluorescence turn-on response when excited at 450 nm. Notably, it also demonstrates the ratiometric fluorescence property while excited by a shorter wavelength (332 nm). All of results suggest probe 2 has a high selectivity toward Cys even in the presence of other amino acids, cations and anions. The detection limit of Cys was calculated as 0.084 μM, which was much lower than the intracellular concentration. 1H NMR, MS and DFT calculation were used to reveal the detection mechanism further. Finally, this low cytotoxic probe was successfully applied in bioimaging within HepG2 cells.

Syntheses of three terbium complexes as fluorescent probes and their application on the pH detection of routine urine test

Co-reporter:Ai-Min Luo, Yongliang Shao, Ke-Jia Zhang, Ya-Wen Wang, Yu Peng

Chinese Chemical Letters 2017 Volume 28, Issue 10(Volume 28, Issue 10) pp:

Publication Date(Web):1 October 2017

DOI:10.1016/j.cclet.2017.08.037

By modifying the salicylic-acid moiety with electron-withdrawing or –donating groups, three new terbium complexes (LI·Tb, LII·Tb, LIII·Tb) based on tripodal carboxylate ligands were synthesized. Due to different pull-push electronic effects of ligands, the fluorescence intensities of these terbium complexes significantly varied, that is: LII·Tb > LIII·Tb > LI·Tb. Meanwhile, the characteristic peaks at 492 nm (5D4 → 7F6) and 547 nm (5D4 → 7F5) showed “Off–On–Off” fluorescence response to various pH conditions, which indicated that all of them can be used as the highly sensitive pH fluorescent probes. Notably, using LII·Tb with the best fluorescence performance as a probe, some patients’ urine samples can be easily monitored through the response triggered by pH value. Therefore, LII·Tb has the potential to auxiliarily diagnose some diseases in clinical practice through pH detection of routine urine test.Download high-res image (138KB)Download full-size imageTerbium complexes were synthesized as probes for the recognition of proton in aqueous solution via fluorescence mode, and it was successful used in the pH detection of routine urine test.

A solvent-tuning fluorescence sensor for In(III) and Al(III) ions and its bioimaging application

Co-reporter:Ya-Wen Wang, Ying-Xi Hua, Hui-Hui Wu, Xin Sun, Yu Peng

Chinese Chemical Letters 2017 Volume 28, Issue 10(Volume 28, Issue 10) pp:

Publication Date(Web):1 October 2017

DOI:10.1016/j.cclet.2017.07.019

A fluorescence-enhanced probe PY, which is based on integration of pyrene moiety and amino acid group, was developed for the orthogonal recognition of In3+ and Al3+ by the quick formation of 1:1 complex. PY shows high selectivity and sensitivity for In3+ in NaOAc/HOAc (pH 4.8) buffer solution but rather for Al3+ in methanol. Moreover, this probe shows good cell permeability, and the recognition of In3+ by PY was successfully applied in bioimaging, which was the first example for detection of this metal ion in living cells.Download high-res image (85KB)Download full-size imageA bifunctional and sensitive chemosensor for In3+ and Al3+ by switching solvent is developed.

Two fluorescein-based chemosensors for the fast detection of 2,4,6-trinitrophenol (TNP) in water

Co-reporter:Zhen-Hai Fu;Ya-Wen Wang

Chemical Communications 2017 vol. 53(Issue 76) pp:10524-10527

Publication Date(Web):2017/09/21

DOI:10.1039/C7CC05966C

Two fluorescein-based chemosensors have been developed. They exhibited rapid and selective detection of 2,4,6-trinitrophenol (TNP) via fluorescence quenching both in ethanol and water solution when excited by visible light.

A fluorescein-based chemosensor for relay fluorescence recognition of Cu(II) ions and biothiols in water and its applications to a molecular logic gate and living cell imaging

Co-reporter:Zhen-Hai Fu;Lu-Bin Yan;Xiaolong Zhang;Fan-Fan Zhu;Xin-Long Han;Jianguo Fang;Ya-Wen Wang

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 19) pp:4115-4121

Publication Date(Web):2017/05/16

DOI:10.1039/C7OB00525C

Relay recognition of copper(II) ions and biothiols via a fluorescence “on–off–on” cascade was designed and realized as a new sequential combination of cations and small molecules. Probe 1 bearing a fluorescein skeleton was thus synthesized, which performed well in 100% HEPES buffer (pH = 7.0) solution, as a highly sensitive, selective fluorescence sensor for Cu2+. The limit of detection (LOD, 0.017 ppm) was obtained, and this value is much lower than 1.3 ppm, allowed by US EPA. The 1 : 1 complex generated from fast sensing of Cu2+ when excited at 491 nm, showed good relay recognition for biothiols (i.e., Cys, Hcy and GSH with low detection limits of 0.12 μM, 0.036 μM and 0.024 μM, respectively) via remarkable fluorescence enhancement. The origin of this relay process was disclosed through ESI-MS and corresponding density functional theory (DFT) computations. Notably, probe 1 can be utilized for the construction of a molecular logic gate with the IMPLICATION function by using the above fluorescence changes. Moreover, this relay recognition was also applied to HepG2 cell imaging successfully.

Stereospecific Synthesis of Tetrahydronaphtho[2,3-b]furans Enabled by a Nickel-Promoted Tandem Reductive Cyclization

Co-reporter:Yu Peng, Jian Xiao, Xiao-Bo Xu, Shu-Ming Duan, Li Ren, Yong-Liang Shao, and Ya-Wen Wang

Organic Letters 2016 Volume 18(Issue 19) pp:5170-5173

Publication Date(Web):September 23, 2016

DOI:10.1021/acs.orglett.6b02665

A Ni-mediated cascade to a stereoselective synthesis of trans-tetrahydronaphtho[2,3-b]furans is efficiently achieved for the first time. The mild reductive system can be easily generated from inexpensive and air-stable materials and shows a broad positional tolerance of substituents that were previously difficult or impossible to access by other methods. Facile syntheses toward new analogues of therapeutic agents (iso)deoxypodophyllotoxin are also reported. In addition, the inherent substrate control is disclosed for the observed unique stereoselectivities during cyclizations.

A fluorescent probe for relay recognition of homocysteine and Group IIIA ions including Ga(III)

Co-reporter:Ya-Wen Wang, Shun-Bang Liu, Wei-Jian Ling and Yu Peng

Chemical Communications 2016 vol. 52(Issue 4) pp:827-830

Publication Date(Web):05 Nov 2015

DOI:10.1039/C5CC07886E

Challenging relay recognition of Hcy and Ga3+, has been realized for the first time. Chemodosimeter 1 bearing a 1,1′-binaphthyl skeleton is a fluorescence turn-on probe for Hcy over Cys. The system (2) generated from the recognition of Hcy exhibited further fluorescence enhancement for Ga3+, which is the first example for specific fluorescent recognition of this metal ion.

A Terbium(III)-Complex-Based On–Off Fluorescent Chemosensor for Phosphate Anions in Aqueous Solution and Its Application in Molecular Logic Gates

Co-reporter:Ya-Wen Wang, Shun-Bang Liu, Yan-Ling Yang, Peng-Zhi Wang, Ai-Jiang Zhang, and Yu Peng

ACS Applied Materials & Interfaces 2015 Volume 7(Issue 7) pp:4415

Publication Date(Web):January 28, 2015

DOI:10.1021/am5089346

A new Tb(III) complex based on a tripodal carboxylate ligand has been synthesized for the selective fluorescent recognition of phosphate anions, including inorganic phosphates and nucleoside phosphates (e.g., ATP), in Tris buffer solution. The resulting L·Tb complex shows the characteristic emission bands centered at about 495 and 550 nm from the Tb(III)-centered 5D4 excited state to 7FJ transitions with J = 6 and 5, where the chelating ligand acts only as an “antenna”. Upon the addition of phosphate anions to the aqueous solution of Tb(III) complex, significant “on–off” fluorescence changes were observed, which were attributed to the inhibition of the “antenna” effect between the ligand and Tb(III) after the incorporation of phosphate anions. Furthermore, this unique Tb(III) complex has been successfully utilized to detect phosphate anions with filter papers and hydrogels. Notably, the Tb(III) complex also can be used for the construction of molecular logic gates with TRANSFER and INHIBIT logic functions by using the above fluorescence changes.Keywords: chemosensor; fluorescence; molecular logic gate; phosphate anions; Tb(III) complex

Concise synthesis of the DEFG ring system in rubriflordilactone B

Co-reporter:Yu Peng, Shu-Ming Duan, Ya-Wen Wang

Tetrahedron Letters 2015 Volume 56(Issue 30) pp:4509-4511

Publication Date(Web):22 July 2015

DOI:10.1016/j.tetlet.2015.05.117

The first synthesis of 6,5,5,5-tetracyclic moiety related with promising anti-HIV activity in rubriflordilactone B has been efficiently achieved. Our strategy started from cheap materials, and features the utilization of radical 1,5-H abstraction/cyclization and vinylogous Mukaiyama aldol reaction, which successfully established the array of five continuous stereogenic carbon centers in the target.The first synthesis of 6,5,5,5-tetracyclic moiety related with promising anti-HIV activity in rubriflordilactone B has been achieved.

Nickel-mediated stereocontrolled synthesis of spiroketals via tandem cyclization–coupling of β-bromo ketals and aryl iodides

Co-reporter:Yu Peng, Xiao-Bo Xu, Jian Xiao and Ya-Wen Wang

Chemical Communications 2014 vol. 50(Issue 4) pp:472-474

Publication Date(Web):04 Nov 2013

DOI:10.1039/C3CC47780K

A ketal-tether approach for the stereoselective synthesis of [5,5] and [5,6]-spiroketals based on reductive coupling catalyzed by the readily available Ni complex is demonstrated. Either an intermolecular or an intramolecular stereospecific cascade has been achieved as well.

A bifunctional, colorimetric and fluorescent probe for recognition of Cu2+ and Hg2+ and its application in molecular logic gate

Co-reporter:YanLing Yang;YaWen Wang

Science China Chemistry 2014 Volume 57( Issue 2) pp:289-295

Publication Date(Web):2014 February

DOI:10.1007/s11426-013-4999-1

A bifunctional probe 1 with iminocoumarin scaffold demonstrated different responses for Cu2+ and Hg2+. In fluorescence mode of probe 1, the intensity at 528 nm was quenched severely upon the addition of Cu2+ or Hg2+. Meanwhile, a new fluorescence band at 574 nm appeared in the case of Hg2+. In its UV-Vis absorption mode, significant hypochromic shift for Cu2+ and bathochromic shift for Hg2+ occurred, which are in agreement with the observation of distinct color changes. In addition, probe 1 can be used for the construction of a molecular logic gate with NOR and INHIBIT logic functions.

Nickel-Mediated Inter- and Intramolecular C–S Coupling of Thiols and Thioacetates with Aryl Iodides at Room Temperature

Co-reporter:Xiao-Bo Xu, Jian Liu, Jian-Jian Zhang, Ya-Wen Wang, and Yu Peng

Organic Letters 2013 Volume 15(Issue 3) pp:550-553

Publication Date(Web):January 15, 2013

DOI:10.1021/ol303366u

A Ni(0)-catalyzed intermolecular cross-coupling of various functionalized thiols and aryl iodides has been developed and successfully extended to less explored intramolecular versions, where thioacetates could also be utilized as the strategic surrogate. Air-stable precatalysts, very mild conditions, and an easy protocol allow rapid access to medicinally useful aryl thioethers, as demonstrated in the facile synthesis of (±)-chuangxinmycin as a key step.

Off–on–off fluorescent chemosensor for pH measurement with a terbium(III) complex based on a tripodal salicylic-acid derivative

Co-reporter:Yan-Ling Yang, Ya-Wen Wang, Dong-Zhu Duan, Ai-Jiang Zhang, Jian-Guo Fang and Yu Peng

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 40) pp:6960-6966

Publication Date(Web):20 Aug 2013

DOI:10.1039/C3OB41319E

New Tb(III) and Eu(III) complexes have been synthesized as potential pH probes using a tripodal substituted-salicylic ligand (H3BSA). Among them, this carboxylate ligand is found to be a good sensitizer for Tb(III) emission owing to the superior match of the triplet energy level of the ligand with the 5D4 emitting level of Tb(III). The resulting BSA·Tb complex exhibited high sensitivity in the physiological pH range with significant “off–on–off” fluorescence changes in aqueous solution. Furthermore, this unique rare-earth complex has been successfully used to monitor pH variations within HeLa cells and with filter papers.

Total synthesis of (±)-sacidumlignans D and A through Ueno–Stork radical cyclization reaction

Co-reporter:Jian-Jian Zhang, Chang-Song Yan, Yu Peng, Zhen-Biao Luo, Xiao-Bo Xu and Ya-Wen Wang

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 15) pp:2498-2513

Publication Date(Web):12 Feb 2013

DOI:10.1039/C3OB00053B

Efficient synthesis of (±)-sacidumlignan D (4) has been successfully achieved employing Ueno–Stork radical cyclization of α-bromo acetal 21 as a key step. Two synthetic approaches for the symmetrical diaryl ketone 19 have been discussed in detail. Notably, sacidumlignan A (1) can be also efficiently synthesized in only 7 steps with 25% overall yield, where acid triggered tandem reaction starting from analogous Ueno–Stork cyclization product 27 played an important role. Moreover, potentially biomimetic conversion from (±)-sacidumlignan D (4) to sacidumlignan A (1) could be realized.

Collective synthesis of several 2,7′-cyclolignans and their correlation by chemical transformations

Co-reporter:Yu Peng, Zhen-Biao Luo, Jian-Jian Zhang, Long Luo and Ya-Wen Wang

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 43) pp:7574-7586

Publication Date(Web):19 Sep 2013

DOI:10.1039/C3OB41672K

Collective synthesis of anti-malarial 2,7′-cyclolignans has been stereoselectively achieved employing (±)-cyclogalgravin (2) as a linchpin through a series of functional group conversions, including redox reactions. Interestingly, 2 can be correlated with the neolignan (±)-kadangustin J (1) isolated from a different plant source, through a highly efficient dehydrative cyclization reaction with excellent diastereotopic differentiation of the veratryl group and concomitant construction of the C1–C7 bond. It is noteworthy that the first total synthesis of stereodivergent (±)-8,8′-epi-aristoligone (5), (±)-8′-epi-aristoligone (7), (±)-8′-epi-8-OH-aristoligone (8) and (±)-8′-epi-aristoligol (9) was demonstrated.

Colorimetric and Fluorescent Chemosensors for the Detection of 2,4,6-Trinitrophenol and Investigation of their Co-Crystal Structures

Co-reporter:Ming Dong;Dr. Ya-Wen Wang;Dr. Ai-Jiang Zhang;Dr. Yu Peng

Chemistry – An Asian Journal 2013 Volume 8( Issue 6) pp:1321-1330

Publication Date(Web):

DOI:10.1002/asia.201300159

Abstract

A full account of our studies of 2,4,6-trinitrophenol (TNP) sensing is provided. A series of chemosensors 2, 3, 4, 5 with a variety of aromatic chromophores for specific recognition of TNP has been designed and then realized through the fluorescence “on/off” mechanism. These chemosensors demonstrated highly selective, sensitive, and fluorescent quenching of TNP with remarkable visual changes through the intramolecular charge-transfer (ICT) process. Their host–guest interactions were investigated by ¹H NMR spectroscopic titrations and their corresponding co-crystal structures, which showed that the 1:1 host–guest complexes were formed by multiple hydrogen-bond interactions in solution or in the solid state. The origins of the significant affinity demonstrated during the fluorescence recognition process were further disclosed through DFT calculations of corresponding compounds.

Ni-Catalyzed Reductive Homocoupling of Unactivated Alkyl Bromides at Room Temperature and Its Synthetic Application

Co-reporter:Yu Peng, Long Luo, Chang-Song Yan, Jian-Jian Zhang, and Ya-Wen Wang

The Journal of Organic Chemistry 2013 Volume 78(Issue 21) pp:10960-10967

Publication Date(Web):October 2, 2013

DOI:10.1021/jo401936v

A room-temperature Ni-catalyzed reductive approach to homocoupling of unactivated primary, secondary, and tertiary alkyl bromides is described. The catalytic system can be easily generated from air-stable and cheap materials and demonstrates broad functional group tolerance, thus allowing facile access to useful dimeric triterpene and lignan-like molecules. Moreover, the dimerization of tertiary bromide 6 efficiently establishes sterically hindered vicinal quaternary carbons (C3a and C3a′), which is a key linkage of intriguing bispyrrolo[2,3-b]indoline alkaloids, thereby enabling us to complete the total syntheses of racemic chimonanthine (9) and folicanthine (10). In addition, this dimerization method can be expanded to the highly stereoselective synthesis of bisperhydrofuro[2,3-b]furan (5a) and the dimeric spiroketal 5b, signifying the involvement of possible radical species.

A Selective and Ratiometric Bifunctional Fluorescent Probe for Al3+ Ion and Proton

Co-reporter:Xin Sun, Ya-Wen Wang, and Yu Peng

Organic Letters 2012 Volume 14(Issue 13) pp:3420-3423

Publication Date(Web):June 26, 2012

DOI:10.1021/ol301390g

A new bifunctional probe based on a pyrene–amino acid conjugate for the differential response of Al3+ and H+ was demonstrated for the first time. Interestingly, two solvent-dependent sensing mechanisms for Al3+, which feature a ratiometric change from excimer to monomer in CH3OH and a turn-on response in water, are also disclosed.

A highly selective fluorescence-enhanced chemosensor for Al3+ in aqueous solution based on a hybrid ligand from BINOL scaffold and β-amino alcohol

Co-reporter:Ming Dong, Yu-Man Dong, Tian-Hua Ma, Ya-Wen Wang, Yu Peng

Inorganica Chimica Acta 2012 Volume 381() pp:137-142

Publication Date(Web):15 February 2012

DOI:10.1016/j.ica.2011.08.043

A chemosensor (R)-OH bearing an amino alcohol group was synthesized for the highly selective fluorescent recognition of Al3+ with low limit of detection (16 ppb). “Turn-on” type fluorescence changes were observed upon the addition of Al3+ in aqueous solution. The significant enhancement (35.4-fold) of fluorescence intensity was ascribed to the complex formation between (R)-OH and Al3+ which denoted as the chelation-enhanced fluorescence (CHEF) process.Graphical abstractA chemosensor (R)-OH bearing an amino alcohol group was synthesized for the highly selective fluorescent recognition of Al3+ with low limit of detection (16 ppb). “Turn-on” type fluorescence changes were observed upon the addition of Al3+ in aqueous solution.Highlights► A chemosensor (R)-OH bearing an amino alcohol group was synthesized. ► (R)-OH presents the highly selective fluorescent recognition of Al3+. ► “Turn-on” type fluorescence changes were observed upon the addition of Al3+ in aqueous solution. ► A dramatic 35.4-fold fluorescence enhancement was observed. ► It has the lower detection limit (16 ppb).

Nickel-Mediated Inter- and Intramolecular Reductive Cross-Coupling of Unactivated Alkyl Bromides and Aryl Iodides at Room Temperature

Co-reporter:Chang-Song Yan;Dr. Yu Peng;Xiao-Bo Xu;Dr. Ya-Wen Wang

Chemistry - A European Journal 2012 Volume 18( Issue 19) pp:6039-6048

Publication Date(Web):

DOI:10.1002/chem.201200190

Abstract

A nickel-mediated intermolecular reductive cross-coupling reaction of unactivated alkyl bromides and aryl iodides at room temperature has been developed and successfully extended to less explored intramolecular versions and tandem cyclization-intermolecular cross-coupling. Highly stereoselective (or stereospecific) synthesis of linear-fused perhydrofuro[2,3-b]furan (pyran) and spiroketal skeletons allows rapid access to these useful building blocks, which would be potentially valuable in the synthesis of relevant natural products. A rational explanation for the formation of contiguous stereogenic centers is given.

A Selective, Sensitive, Colorimetric, and Fluorescence Probe for Relay Recognition of Fluoride and Cu(II) Ions with “Off–On–Off” Switching in Ethanol–Water Solution

Co-reporter:Yu Peng, Yu-Man Dong, Ming Dong, and Ya-Wen Wang

The Journal of Organic Chemistry 2012 Volume 77(Issue 20) pp:9072-9080

Publication Date(Web):September 24, 2012

DOI:10.1021/jo301548v

Anion to cation relay recognition was designed and realized for the first time with sequence specificity (F–→Cu2+) via a fluorescence “off–on–off” mechanism. Probe 1 was a highly selective, sensitive, and turn-on chemodosimeter for F– through a specific cyclization reaction triggered by the strong affinity of fluoride toward silicon with a significant change of fluorescence color in both ethanol and ethanol–water (1:1, v/v) solution. Fluorescence enhancement factors were dramatic: 833-fold in ethanol and 164-fold in ethanol–water (1:1, v/v) solution, respectively. The in situ system generated from the sensing of F– showed good relay recognition ability for Cu2+ via fast fluorescence quenching by the formation of a 1:1 complex in ethanol–water (1:1, v/v) solution. The isolated pure compound 2 also exhibited high selectivity toward Cu2+ in PBS buffer (pH = 7.0) solution. The origin of this sequence specificity of fluorescence recognition was disclosed through the crystal or optimized structures and DFT calculations of corresponding compounds.

Synthesis, crystal structures, luminescent and magnetic properties of homodinuclear lanthanide complexes with a flexible tripodal carboxylate ligand

Co-reporter:Ai-Jiang Zhang, Ya-Wen Wang, Wei Dou, Ming Dong, Yan-Ling Zhang, Yu Tang, Wei-Sheng Liu and Yu Peng

Dalton Transactions 2011 vol. 40(Issue 12) pp:2844-2851

Publication Date(Web):10 Feb 2011

DOI:10.1039/C0DT01514H

Six new homodinuclear lanthanide(III) complexes with a flexible tripodal carboxylate ligand (H3L), of formulae [Ln2L2(DMF)4]·4DMF (Ln = La (1), Nd (2), Eu (3), Gd (4), Tb (5), Dy (6), DMF = N, N-Dimethylformamide) have been synthesized. Among them, 1, 2, 3, 4, 6 were characterized by single-crystal X-ray diffraction, which crystallized in the monoclinic space groupP21/n with a = 13.309(2) Å, b = 27.404(4) Å, c = 16.686(3) Å, β = 105.115(2) and V = 5875.2(17) Å3 for 1, a = 13.3016(5) Å, b = 27.1952(12) Å, c = 16.6339(7) Å, β = 105.030(2) and V = 5811.3(4) Å3 for 2, a = 13.2797(10) Å, b = 27.072(2) Å, c = 16.6564(13) Å, β = 104.9390(10) and V = 5785.7(8) Å3 for 3, a = 13.2855(3) Å, b = 27.0074(6) Å, c = 16.6357(3) Å, β = 104.9790(10) and V = 5766.2(2) Å3 for 4, a = 13.2837(5) Å, b = 26.9105(10) Å, c = 16.6066(6) Å, β = 104.917(2) and V = 5736.3(4) Å3 for 6. The crystal structures reveal that these complexes are isostructural, and molecules are connected from 0D to 3D supramolecular structures by hydrogen bonds. All of them were characterized by elemental analysis, IR spectroscopy, XRD and TGA. Unusually, non-luminescent Tb(III) complex was obtained. The photophysical property of the Eu(III) complex and the magnetic property of Gd(III) complex are investigated and discussed in detail.

A Selective, Sensitive, and Chromogenic Chemodosimeter for Cyanide Based on the 1,1′-Binaphthyl Scaffold

Co-reporter:Yu-Man Dong, Yu Peng, Ming Dong, and Ya-Wen Wang

The Journal of Organic Chemistry 2011 Volume 76(Issue 16) pp:6962-6966

Publication Date(Web):July 13, 2011

DOI:10.1021/jo201269e

A highly selective chemodosimeter 1 for cyanide based on the 1,1′-binaphthyl skeleton is described which demonstrated significant visual change and a low limit of detection. Interestingly, a reversible process triggered successively by CN– and Au3+ is also observed and determined by fluorescence, UV–vis spectra, 1H NMR titration, and ESI–MS.

Highly Selective Ratiometric Fluorescent Sensing for Hg2+ and Au3+, Respectively, in Aqueous Media

Co-reporter:Ming Dong, Ya-Wen Wang, and Yu Peng

Organic Letters 2010 Volume 12(Issue 22) pp:5310-5313

Publication Date(Web):October 29, 2010

DOI:10.1021/ol1024585

A nonsulfur probe based on a 1,8-naphthalimide and alkyne conjugate for the ratiometric fluorescent sensing for Hg2+ and Au3+ through the tuning of pH in different aqueous solutions is described. This work provides a novel reaction-based approach for selective recognition of these two ions with significant change of fluorescence color and constitutes the first ratiometric case for Au3+.

A series of highly sensitive and selective fluorescent and colorimetric “off-on” chemosensors for Cu (II) based on rhodamine derivatives

Co-reporter:Ming Dong, Tian-Hua Ma, Ai-Jiang Zhang, Yu-Man Dong, Ya-Wen Wang, Yu Peng

Dyes and Pigments 2010 Volume 87(Issue 2) pp:164-172

Publication Date(Web):October 2010

DOI:10.1016/j.dyepig.2010.03.015

Several rhodamine-B (C.I. Basic Violet 10) hydrazide derivatives were employed as specific fluorescent and colorimetric chemosensors for Cu2+ in neutral buffered media. The probes exhibited selective “off-on” type changes in both absorption and emission spectra toward Cu2+ ions compared to other metal cations, which was attributed to transformation of the non-fluorescent and colorless spirolactam derivative to the ring-opened, fluorescent, pink coloured amide. Further studies of structure-activity relationship revealed that the designated acyl hydrazone skeleton moiety shared by these chemosensors, derived from the dye hydrazide and salicylaldehyde analogues, determines the selectivity for Cu2+ over other cations.

cine Substitution and the Cu Effect in Stille Cross-Coupling Reactions: Mechanistic Perspectives and Synthetic Utility

Co-reporter:Yu Peng;Wei-Dong Z. Li

European Journal of Organic Chemistry 2010 Volume 2010( Issue 35) pp:6703-6718

Publication Date(Web):

DOI:10.1002/ejoc.201000557

Abstract

cine Substitution arising from slow transmetallation occasionally occurs in classic Pd-catalyzed Stille cross-coupling reactions with sterically hindered vinyltin components. Mechanistic explanations of this “abnormal” cross-coupling mode and the intriguing co-catalytic effects of metallic Cu species in restoring the ipso selectivity are summarized. Typical synthetic applications of this unique Cu effect and the advent of Cu-catalyzed Stille-type cross-coupling are also demonstrated.

A simply and highly selective “turn-on” type fluorescent chemosensor for Hg2+ based on chiral BINOL-Schiff’s base ligand

Co-reporter:Tian-Hua Ma, Ai-Jiang Zhang, Ming Dong, Yu-Man Dong, Yu Peng, Ya-Wen Wang

Journal of Luminescence 2010 Volume 130(Issue 5) pp:888-892

Publication Date(Web):May 2010

DOI:10.1016/j.jlumin.2009.12.030

A chiral BINOL derivative bearing Schiff’s base group has been synthesized for the selective fluorescent recognition of Hg2+. Highly selective “turn-on” type fluorescence changes were observed upon the addition of Hg2+. The fluorescence intensity enhancement was ascribed to the complex formation between (R)-1 and Hg2+ which blocked the photo-induced electron transfer process.

A Unique Water-Tuning Dual-Channel Fluorescence-Enhanced Sensor for Aluminum Ions Based on a Hybrid Ligand from a 1,1-Binaphthyl Scaffold and an Amino Acid

Co-reporter:Tian-Hua Ma;Ming Dong;Yu-Man Dong;Dr. Ya-Wen Wang ;Dr. Yu Peng

Chemistry - A European Journal 2010 Volume 16( Issue 34) pp:10313-10318

Publication Date(Web):

DOI:10.1002/chem.201001431

Fluorescent sensors for Ca2+ and Pb2+ based on binaphthyl derivatives

Co-reporter:Ya-Wen Wang, Yong-Tao Shi, Yu Peng, Ai-Jiang Zhang, Tian-Hua Ma, Wei Dou, Jiang-Rong Zheng

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2009 Volume 72(Issue 2) pp:322-326

Publication Date(Web):March 2009

DOI:10.1016/j.saa.2008.09.013

Two novel binaphthyl compounds have been synthesized for the selective fluorescent recognition of Ca2+ or Pb2+. By introducing different terminal groups to the receptor unit, the fluorescence signals of the receptors are significantly changed: 1 is fluorescence enhancement for Ca2+, 2 is fluorescence quenching for Pb2+. The binding properties for metal ions were examined by the absorption and fluorescence spectra. The fluorescence intensity enhancement was ascribed to the complex formation between Ca2+ and 1 which blocked the photo-induced electron transfer process.

Nickel-mediated stereocontrolled synthesis of spiroketals via tandem cyclization–coupling of β-bromo ketals and aryl iodides

Co-reporter:Yu Peng, Xiao-Bo Xu, Jian Xiao and Ya-Wen Wang

Chemical Communications 2014 - vol. 50(Issue 4) pp:NaN474-474

Publication Date(Web):2013/11/04

DOI:10.1039/C3CC47780K

A ketal-tether approach for the stereoselective synthesis of [5,5] and [5,6]-spiroketals based on reductive coupling catalyzed by the readily available Ni complex is demonstrated. Either an intermolecular or an intramolecular stereospecific cascade has been achieved as well.

A fluorescein-based chemosensor for relay fluorescence recognition of Cu(II) ions and biothiols in water and its applications to a molecular logic gate and living cell imaging

Co-reporter:Zhen-Hai Fu, Lu-Bin Yan, Xiaolong Zhang, Fan-Fan Zhu, Xin-Long Han, Jianguo Fang, Ya-Wen Wang and Yu Peng

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 19) pp:NaN4121-4121

Publication Date(Web):2017/03/28

DOI:10.1039/C7OB00525C

Relay recognition of copper(II) ions and biothiols via a fluorescence “on–off–on” cascade was designed and realized as a new sequential combination of cations and small molecules. Probe 1 bearing a fluorescein skeleton was thus synthesized, which performed well in 100% HEPES buffer (pH = 7.0) solution, as a highly sensitive, selective fluorescence sensor for Cu2+. The limit of detection (LOD, 0.017 ppm) was obtained, and this value is much lower than 1.3 ppm, allowed by US EPA. The 1:1 complex generated from fast sensing of Cu2+ when excited at 491 nm, showed good relay recognition for biothiols (i.e., Cys, Hcy and GSH with low detection limits of 0.12 μM, 0.036 μM and 0.024 μM, respectively) via remarkable fluorescence enhancement. The origin of this relay process was disclosed through ESI-MS and corresponding density functional theory (DFT) computations. Notably, probe 1 can be utilized for the construction of a molecular logic gate with the IMPLICATION function by using the above fluorescence changes. Moreover, this relay recognition was also applied to HepG2 cell imaging successfully.

Off–on–off fluorescent chemosensor for pH measurement with a terbium(III) complex based on a tripodal salicylic-acid derivative

Co-reporter:Yan-Ling Yang, Ya-Wen Wang, Dong-Zhu Duan, Ai-Jiang Zhang, Jian-Guo Fang and Yu Peng

Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 40) pp:NaN6966-6966

Publication Date(Web):2013/08/20

DOI:10.1039/C3OB41319E

New Tb(III) and Eu(III) complexes have been synthesized as potential pH probes using a tripodal substituted-salicylic ligand (H3BSA). Among them, this carboxylate ligand is found to be a good sensitizer for Tb(III) emission owing to the superior match of the triplet energy level of the ligand with the 5D4 emitting level of Tb(III). The resulting BSA·Tb complex exhibited high sensitivity in the physiological pH range with significant “off–on–off” fluorescence changes in aqueous solution. Furthermore, this unique rare-earth complex has been successfully used to monitor pH variations within HeLa cells and with filter papers.

A fluorescent probe for relay recognition of homocysteine and Group IIIA ions including Ga(III)

Co-reporter:Ya-Wen Wang, Shun-Bang Liu, Wei-Jian Ling and Yu Peng

Chemical Communications 2016 - vol. 52(Issue 4) pp:NaN830-830

Publication Date(Web):2015/11/05

DOI:10.1039/C5CC07886E

Challenging relay recognition of Hcy and Ga3+, has been realized for the first time. Chemodosimeter 1 bearing a 1,1′-binaphthyl skeleton is a fluorescence turn-on probe for Hcy over Cys. The system (2) generated from the recognition of Hcy exhibited further fluorescence enhancement for Ga3+, which is the first example for specific fluorescent recognition of this metal ion.

Synthesis, crystal structures, luminescent and magnetic properties of homodinuclear lanthanide complexes with a flexible tripodal carboxylate ligand

Co-reporter:Ai-Jiang Zhang, Ya-Wen Wang, Wei Dou, Ming Dong, Yan-Ling Zhang, Yu Tang, Wei-Sheng Liu and Yu Peng

Dalton Transactions 2011 - vol. 40(Issue 12) pp:NaN2851-2851

Publication Date(Web):2011/02/10

DOI:10.1039/C0DT01514H

Six new homodinuclear lanthanide(III) complexes with a flexible tripodal carboxylate ligand (H3L), of formulae [Ln2L2(DMF)4]·4DMF (Ln = La (1), Nd (2), Eu (3), Gd (4), Tb (5), Dy (6), DMF = N, N-Dimethylformamide) have been synthesized. Among them, 1, 2, 3, 4, 6 were characterized by single-crystal X-ray diffraction, which crystallized in the monoclinic space groupP21/n with a = 13.309(2) Å, b = 27.404(4) Å, c = 16.686(3) Å, β = 105.115(2) and V = 5875.2(17) Å3 for 1, a = 13.3016(5) Å, b = 27.1952(12) Å, c = 16.6339(7) Å, β = 105.030(2) and V = 5811.3(4) Å3 for 2, a = 13.2797(10) Å, b = 27.072(2) Å, c = 16.6564(13) Å, β = 104.9390(10) and V = 5785.7(8) Å3 for 3, a = 13.2855(3) Å, b = 27.0074(6) Å, c = 16.6357(3) Å, β = 104.9790(10) and V = 5766.2(2) Å3 for 4, a = 13.2837(5) Å, b = 26.9105(10) Å, c = 16.6066(6) Å, β = 104.917(2) and V = 5736.3(4) Å3 for 6. The crystal structures reveal that these complexes are isostructural, and molecules are connected from 0D to 3D supramolecular structures by hydrogen bonds. All of them were characterized by elemental analysis, IR spectroscopy, XRD and TGA. Unusually, non-luminescent Tb(III) complex was obtained. The photophysical property of the Eu(III) complex and the magnetic property of Gd(III) complex are investigated and discussed in detail.

Collective synthesis of several 2,7′-cyclolignans and their correlation by chemical transformations

Co-reporter:Yu Peng, Zhen-Biao Luo, Jian-Jian Zhang, Long Luo and Ya-Wen Wang

Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 43) pp:NaN7586-7586

Publication Date(Web):2013/09/19

DOI:10.1039/C3OB41672K

Collective synthesis of anti-malarial 2,7′-cyclolignans has been stereoselectively achieved employing (±)-cyclogalgravin (2) as a linchpin through a series of functional group conversions, including redox reactions. Interestingly, 2 can be correlated with the neolignan (±)-kadangustin J (1) isolated from a different plant source, through a highly efficient dehydrative cyclization reaction with excellent diastereotopic differentiation of the veratryl group and concomitant construction of the C1–C7 bond. It is noteworthy that the first total synthesis of stereodivergent (±)-8,8′-epi-aristoligone (5), (±)-8′-epi-aristoligone (7), (±)-8′-epi-8-OH-aristoligone (8) and (±)-8′-epi-aristoligol (9) was demonstrated.

Total synthesis of (±)-sacidumlignans D and A through Ueno–Stork radical cyclization reaction

Co-reporter:Jian-Jian Zhang, Chang-Song Yan, Yu Peng, Zhen-Biao Luo, Xiao-Bo Xu and Ya-Wen Wang

Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 15) pp:NaN2513-2513

Publication Date(Web):2013/02/12

DOI:10.1039/C3OB00053B

Efficient synthesis of (±)-sacidumlignan D (4) has been successfully achieved employing Ueno–Stork radical cyclization of α-bromo acetal 21 as a key step. Two synthetic approaches for the symmetrical diaryl ketone 19 have been discussed in detail. Notably, sacidumlignan A (1) can be also efficiently synthesized in only 7 steps with 25% overall yield, where acid triggered tandem reaction starting from analogous Ueno–Stork cyclization product 27 played an important role. Moreover, potentially biomimetic conversion from (±)-sacidumlignan D (4) to sacidumlignan A (1) could be realized.

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