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Jingbo Lan

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Name: 兰静波; Lan, JingBo
Organization: Sichuan University , China
Department: College of Chemistry
Title: Professor(PhD)

TOPICS

An Effective Strategy to Construct Highly Efficient Deep-Blue Organic Light-Emitting Field-Effect Transistors
Co-reporter:Guoqiang Tang;Bijin Li;Jingsong You
Advanced Materials Interfaces 2017 Volume 4(Issue 17) pp:
Publication Date(Web):2017/09/01
DOI:10.1002/admi.201700453
The fabrication of highly efficient deep-blue organic light-emitting field-effect transistors (OLEFETs) remains a challenge due to the large energy bandgap of deep-blue emitters. In this work, an effective strategy is developed by combining an ambipolar charge transport material with an efficient deep-blue fluorescent emitter that features the hybridized local and charge-transfer (HLCT) excited state character in a trilayer device architecture. The ambipolar nature of charge transport material endows the device with a relatively high hole–electron recombination efficiency, while the HLCT excited state character of the emitter offers the device a high singlet exciton yield. The device exhibits a maximum brightness of 710 cd m−2 and a maximum external quantum efficiency (EQE) of 0.28%, which is the first example of deep-blue OLEFETs. Unlike conventional OLEFETs, the devices presented herein display high EQEs during almost the entire illumination. The EQE of device at the maximum brightness reaches 0.20%, which is the highest value among the reported blue OLEFETs. Moreover, the device exhibits an excellent color purity with a sharp emission peak at 445 nm, a narrow full-width at half-maximum of 58 nm, and a Commission Internationale de l'Eclairage coordinates of (0.15, 0.06) that is very close to the National Television System Committee standard blue (0.14, 0.08).
Molecular Engineering of Mechanochromic Materials by Programmed C–H Arylation: Making a Counterpoint in the Chromism Trend
Co-reporter:Jie Wu, Yangyang Cheng, Jingbo Lan, Di Wu, Shengyou Qian, Lipeng Yan, Zhen He, Xiaoyu Li, Kai Wang, Bo Zou, and Jingsong You
Journal of the American Chemical Society 2016 Volume 138(Issue 39) pp:12803-12812
Publication Date(Web):September 7, 2016
DOI:10.1021/jacs.6b03890
The development of facile methods for screening organic functional molecules through C–H bond activation is a revolutionary trend in materials research. The prediction of mechanochromism as well as mechanochromic trends of luminogens is an appealing yet challenging puzzle. Here, we present a strategy for the design of mechanochromic luminogens based on the dipole moment of donor–acceptor molecules. For this purpose, a highly efficient route to 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines (2,7-diaryl-TAPs) has been established through programmed C–H arylation, which unlocks a great opportunity to rapidly assemble a library of fluorophores for the discovery of mechanochromic regularity. Molecular dipole moment can be employed to explain and further predict the mechanochromic trends. The 2,7-diaryl-TAPs with electron-donating groups on the 2-aryl and electron-withdrawing groups on the 7-aryl possess a relatively small dipole moment and exhibit a red-shifted mechanochromism. When the two aryls are interchanged, the resulting luminogens have a relatively large dipole moment and display a blue-shifted mechanochromism. Seven pairs of isomers with opposite mechanochromic trends are presented as illustrative examples. The aryl-interchanged congeners with a bidirectional emission shift are structurally similar, which provides an avenue for understanding in-depth the mechanochromic mechanism.
Chelation-assisted Pd-catalysed ortho-selective oxidative C–H/C–H cross-coupling of aromatic carboxylic acids with arenes and intramolecular Friedel–Crafts acylation: one-pot formation of fluorenones
Co-reporter:Denan Sun, Bijin Li, Jingbo Lan, Quan Huang and Jingsong You  
Chemical Communications 2016 vol. 52(Issue 18) pp:3635-3638
Publication Date(Web):28 Jan 2016
DOI:10.1039/C6CC00103C
Pd-Catalysed ortho-selective oxidative C–H/C–H cross-coupling of aromatic carboxylic acids with arenes and subsequent intramolecular Friedel–Crafts acylation has been accomplished for the first time through a chelation-assisted C–H activation strategy. Starting from the readily available substrates, a variety of fluorenone derivatives are obtained in one pot. The direct use of naturally occurring carboxylic acid functionalities as directing groups avoids unnecessary steps for installation and removal of an extra directing group.
Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp2)–H arylation
Co-reporter:Qian Wu, Chenglong Du, Yumin Huang, Xingyan Liu, Zhen Long, Feijie Song and Jingsong You  
Chemical Science 2015 vol. 6(Issue 1) pp:288-293
Publication Date(Web):09 Oct 2014
DOI:10.1039/C4SC02070G
Based on the well-defined five-membered aryl gold(III) complexes, [Au(tpy)X2] (3a and 3b) and [AuBr(Ph)(tpy)] (7), as well as the aryl gold(III) complex [AuCl2(Ph)(tpy)] (8) (tpy = 2-(o-tolyl)pyridine) as reliable models, we present a detailed study of the mechanism for gold(III)-catalyzed oxidative cross-coupling reactions between cycloaurable arenes and arylboronic acids. Here we report the direct evidence for a mechanistic proposal including arene C–H activation, transmetallation and biaryl reductive elimination. The chelation-assisted C–H activation strategy has been used for the development of the gold(III)-catalyzed C–H bond arylation of arenes with aryl reagents to forge extended π-conjugated systems.
Novel Ruthenium Sensitizers with a Phenothiazine Conjugated Bipyridyl Ligand for High-Efficiency Dye-Sensitized Solar Cells
Co-reporter:Zhijie She, Yangyang Cheng, Luoqiang Zhang, Xiaoyu Li, Di Wu, Qiang Guo, Jingbo Lan, Ruilin Wang, and Jingsong You
ACS Applied Materials & Interfaces 2015 Volume 7(Issue 50) pp:27831
Publication Date(Web):December 1, 2015
DOI:10.1021/acsami.5b09160
Two efficient ruthenium sensitizers with a phenothiazine-modified bipyridine as an ancillary ligand, coded SCZ-1 and SCZ-2, have been developed as dyes in dye-sensitized solar cells (DSSCs). Both sensitizers exhibit low-energy metal-to-ligand charge transfer (MLCT) bands centered at 539 nm with high molar extinction coefficients of 1.77 × 104 M–1 cm–1 for SCZ-1 and 1.66 × 104 M–1 cm–1 for SCZ-2, which are significantly higher than the corresponding value for the reference N719 (1.27 × 104 M–1 cm–1), indicating that the light-harvesting capacity of ruthenium sensitizers can be reinforced by introducing phenothiazine moieties into the bipyridine ligand. Under AM 1.5G irradiation (100 mW cm–2), SCZ-1 and SCZ-2 sensitized DSSC devices show impressive power conversion efficiencies (PCE) up to 10.4% by using of iodide-based electrolytes, which exceeds that of N719 (9.9%) under the same conditions. Both of the open circuit voltage (VOC) and fill factor (FF) of SCZ-sensitized solar cells approximate to those of N719-sensitized cell. The relatively higher efficiencies of the SCZ-sensitized cells than that of N719-sensitized cell come from their higher short-circuit photocurrent density (JSC), which may be mainly attributed to the high absorption coefficient. The absorption spectrum and device efficiency of SCZ-1 are both quite close to those of SCZ-2, suggesting that the difference in alkyl chains on the N atom of phenothiazine is not a decisive factor in affecting the photovoltaic performance of dyes.Keywords: dye-sensitized solar cell; high-efficiency; light-harvesting capacity; phenothiazine; ruthenium sensitizer
Aldehyde as a Traceless Directing Group for Rh(III)-Catalyzed C–H Activation: A Facile Access to Diverse Indolo[1,2-a]quinolines
Co-reporter:Xingyan Liu, Xiaoyu Li, Hu Liu, Qiang Guo, Jingbo Lan, Ruilin Wang, and Jingsong You
Organic Letters 2015 Volume 17(Issue 12) pp:2936-2939
Publication Date(Web):May 29, 2015
DOI:10.1021/acs.orglett.5b01171
The aldehyde group has been developed for the first time as a traceless directing group to promote regioselective Rh(III)-catalyzed C–H activation/cyclization of indolyl aldehydes with alkynes. This protocol streamlines access to a variety of appealing indolo[1,2-a]quinoline structures. As illustrative examples, a concise three-step synthesis of indolo[1,2-a]quinoline-based sensitizers is accomplished that exhibits the potential of C–H activation in the construction of organic optoelectronic materials.
Rh(III)-Catalyzed Decarboxylative ortho-Heteroarylation of Aromatic Carboxylic Acids by Using the Carboxylic Acid as a Traceless Directing Group
Co-reporter:Xurong Qin, Denan Sun, Qiulin You, Yangyang Cheng, Jingbo Lan, and Jingsong You
Organic Letters 2015 Volume 17(Issue 7) pp:1762-1765
Publication Date(Web):March 23, 2015
DOI:10.1021/acs.orglett.5b00532
Highly selective decarboxylative ortho-heteroarylation of aromatic carboxylic acids with various heteroarenes has been developed through Rh(III)-catalyzed two-fold C–H activation, which exhibits a wide substrate scope of both aromatic carboxylic acids and heteroarenes. The use of naturally occurring carboxylic acid as the directing group avoids troublesome extra steps for installation and removal of an external directing group.
Rh-catalysed direct cyclisation of 1,4-naphthoquinone and 9,10-phenanthraquinone with alkyne: facile access to 1,8-dioxapyrenes and 1,12-dioxaperylenes as orange and red-emitting luminophores
Co-reporter:Jing Wang, Dekun Qin, Jingbo Lan, Yangyang Cheng, Shuai Zhang, Qiang Guo, Jie Wu, Di Wu and Jingsong You  
Chemical Communications 2015 vol. 51(Issue 29) pp:6337-6339
Publication Date(Web):03 Mar 2015
DOI:10.1039/C5CC00312A
Rh-catalysed direct cyclisation of 1,4-naphthoquinones and 9,10-phenanthraquinones with alkynes has been accomplished for the first time through the C–H activation strategy to forge 1,8-dioxapyrenes and 1,12-dioxaperylenes. Starting from readily available substrates, a variety of dipyran-containing PAHs are obtained in one step and exhibit orange/red-emitting performance, large Stokes shifts and high thermal stability.
Cu-catalysed direct C–H (hetero)arylation of [1,2,4]triazolo[4,3-a]pyridine to construct deep-blue-emitting luminophores
Co-reporter:Jie Wu, Qiulin You, Jingbo Lan, Qiang Guo, Xiaoyu Li, Ying Xue and Jingsong You  
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 19) pp:5372-5375
Publication Date(Web):07 Apr 2015
DOI:10.1039/C5OB00552C
Cu-catalysed direct C–H (hetero)arylation of [1,2,4]triazolo[4,3-a]pyridine has been accomplished for the first time to streamline the synthesis of 3-aryl-[1,2,4]triazolo[4,3-a]pyridines for screening blue-emitting materials. On this basis, the photophysical properties of the resulting compounds were systematically investigated, most of which exhibited excellent deep-blue emission with moderate to high quantum yields, photostability, air stability and thermal stability.
Molecular design of new organic sensitizers based on thieno[1,4]benzothiazine for dye-sensitized solar cells
Co-reporter:Hu Liu, Xingrong Liao, Xiaoyu Li, Di Wu, Qiang Guo, Jie Wu, Shengyou Qian, Jingbo Lan, Ruilin Wang and Jingsong You  
RSC Advances 2015 vol. 5(Issue 70) pp:56865-56871
Publication Date(Web):22 Jun 2015
DOI:10.1039/C5RA07785K
A novel thieno[1,4]benzothiazine donor has been developed for the first time to construct metal-free organic sensitizers, which exhibit more dramatically red-shifted absorptions than phenothiazine-based dyes. Under AM 1.5G irradiation, the conversion efficiency of the new dye TBT-1-based DSSC (η = 7.6%) approximates to that of the phenothiazine-based PT-C6, indicating thieno[1,4]benzothiazine would be a promising electron donor for the construction of organic optoelectronic materials.
Rhodium(III)-Catalyzed ortho CH Heteroarylation of (Hetero)aromatic Carboxylic Acids: A Rapid and Concise Access to -Conjugated Poly-heterocycles
Co-reporter:Dr. Xurong Qin;Xiaoyu Li;Quan Huang;Hu Liu;Dr. Di Wu;Qiang Guo;Dr. Jingbo Lan;Dr. Ruilin Wang;Dr. Jingsong You
Angewandte Chemie 2015 Volume 127( Issue 24) pp:7273-7276
Publication Date(Web):
DOI:10.1002/ange.201501982

Abstract

RhIII-catalyzed oxidative CH/CH cross-coupling between (hetero)aromatic carboxylic acids and various heteroarenes has been accomplished to construct highly functionalized ortho-carboxy-substituted bi(hetero)aryls. The use of a carboxy group as the directing group obviates tedious steps for installation and removal of extra directing groups, and enables a facile one-step synthesis of ortho-carboxy bi(hetero)aryls. The method provides opportunities for rapid assembly of a library of important fluorene and coumarin-type poly-heterocycles through intramolecular electrophilic substitution or oxidative lactonization. As illustrative examples, the strategy developed herein greatly streamlines accesses to a variety of appealing polyheterocycles such as DTPO (5H-dithieno[3,2-b:2′,3′-d]pyran-5-one), CPDTO (cyclopentadithiophen-4-one), and indenothiophenes.

Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative CH Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials
Co-reporter:Bijin Li;Dr. Jingbo Lan;Dr. Di Wu ;Dr. Jingsong You
Angewandte Chemie 2015 Volume 127( Issue 47) pp:14214-14218
Publication Date(Web):
DOI:10.1002/ange.201507272

Abstract

Reported herein is the first example of a transition-metal-catalyzed internal oxidative CH/CH cross-coupling between two (hetero)arenes through a traceless oxidation directing strategy. Without the requirement of an external metal oxidant, a wide range of phenols, including phenol-containing natural products, can undergo the coupling with azoles to assemble a large library of highly functionalized 2-(2-hydroxyphenyl)azoles. The route provides an opportunity to rapidly screen white-light-emitting materials. As illustrative examples, two bis(triphenylamine)-bearing 2-(2-hydroxyphenyl)oxazoles, which are difficult to access otherwise, exhibit bright white-light emission, high quantum yield, and thermal stability. Also presented is the first example of the white-light emission, in a single excited-state intramolecular proton transfer system, of 2-(2-hydroxyphenyl)azoles, thus highlighting the charm of CH activation in the discovery of new organic optoelectronic materials.

Rhodium(III)-Catalyzed ortho-Heteroarylation of Phenols through Internal Oxidative CH Activation: Rapid Screening of Single-Molecular White-Light-Emitting Materials
Co-reporter:Bijin Li;Dr. Jingbo Lan;Dr. Di Wu ;Dr. Jingsong You
Angewandte Chemie International Edition 2015 Volume 54( Issue 47) pp:14008-14012
Publication Date(Web):
DOI:10.1002/anie.201507272

Abstract

Reported herein is the first example of a transition-metal-catalyzed internal oxidative CH/CH cross-coupling between two (hetero)arenes through a traceless oxidation directing strategy. Without the requirement of an external metal oxidant, a wide range of phenols, including phenol-containing natural products, can undergo the coupling with azoles to assemble a large library of highly functionalized 2-(2-hydroxyphenyl)azoles. The route provides an opportunity to rapidly screen white-light-emitting materials. As illustrative examples, two bis(triphenylamine)-bearing 2-(2-hydroxyphenyl)oxazoles, which are difficult to access otherwise, exhibit bright white-light emission, high quantum yield, and thermal stability. Also presented is the first example of the white-light emission, in a single excited-state intramolecular proton transfer system, of 2-(2-hydroxyphenyl)azoles, thus highlighting the charm of CH activation in the discovery of new organic optoelectronic materials.

Rhodium(III)-Catalyzed ortho CH Heteroarylation of (Hetero)aromatic Carboxylic Acids: A Rapid and Concise Access to -Conjugated Poly-heterocycles
Co-reporter:Dr. Xurong Qin;Xiaoyu Li;Quan Huang;Hu Liu;Dr. Di Wu;Qiang Guo;Dr. Jingbo Lan;Dr. Ruilin Wang;Dr. Jingsong You
Angewandte Chemie International Edition 2015 Volume 54( Issue 24) pp:7167-7170
Publication Date(Web):
DOI:10.1002/anie.201501982

Abstract

RhIII-catalyzed oxidative CH/CH cross-coupling between (hetero)aromatic carboxylic acids and various heteroarenes has been accomplished to construct highly functionalized ortho-carboxy-substituted bi(hetero)aryls. The use of a carboxy group as the directing group obviates tedious steps for installation and removal of extra directing groups, and enables a facile one-step synthesis of ortho-carboxy bi(hetero)aryls. The method provides opportunities for rapid assembly of a library of important fluorene and coumarin-type poly-heterocycles through intramolecular electrophilic substitution or oxidative lactonization. As illustrative examples, the strategy developed herein greatly streamlines accesses to a variety of appealing polyheterocycles such as DTPO (5H-dithieno[3,2-b:2′,3′-d]pyran-5-one), CPDTO (cyclopentadithiophen-4-one), and indenothiophenes.

Pd-Catalyzed C–H Carbonylation of (Hetero)arenes with Formates and Intramolecular Dehydrogenative Coupling: A Shortcut to Indolo[3,2-c]coumarins
Co-reporter:Jie Wu, Jingbo Lan, Siyuan Guo, and Jingsong You
Organic Letters 2014 Volume 16(Issue 22) pp:5862-5865
Publication Date(Web):November 3, 2014
DOI:10.1021/ol502749b
An efficient protocol for the synthesis of (hetero)aryl carboxylic esters has been achieved by Pd-catalyzed C–H carbonylation of (hetero)arenes with aryl formates. A relatively wide range of functional groups can be tolerated in this transformation, and the corresponding esters are obtained in good yields. On this basis, an intramolecular oxidative C–H/C–H coupling has been developed to prepare indolo[3,2-c]coumarins.
Cu-catalysed oxidative C–H/C–H coupling polymerisation of benzodiimidazoles: an efficient approach to regioregular polybenzodiimidazoles for blue-emitting materials
Co-reporter:Quan Huang, Xurong Qin, Bijin Li, Jingbo Lan, Qiang Guo and Jingsong You  
Chemical Communications 2014 vol. 50(Issue 89) pp:13739-13741
Publication Date(Web):15 Sep 2014
DOI:10.1039/C4CC06291D
The Cu-catalysed oxidative C–H/C–H coupling reaction of azoles has been used for the first time to develop polymerisation, which provides an efficient method for the preparation of polybenzodiimidazoles. These polymers exhibit high molecular weights, regioregularity, blue-emitting performance and thermal stability.
A sensitive colorimetric and fluorescent sensor based on imidazolium-functionalized squaraines for the detection of GTP and alkaline phosphatase in aqueous solution
Co-reporter:Ningjie Wu, Jingbo Lan, Lipeng Yan and Jingsong You  
Chemical Communications 2014 vol. 50(Issue 34) pp:4438-4441
Publication Date(Web):04 Mar 2014
DOI:10.1039/C4CC00752B
Imidazolium-functionalized squaraine ImSQ8 is synthesized as a sensitive colorimetric and fluorescent chemosensor for GTP in aqueous solution. The detection limit of GTP reaches 5.4 ppb. Its applications in the live-cell imaging and enzyme activity assay have also been demonstrated.
Chelation-assisted Rh(III)-catalyzed C2-selective oxidative C–H/C–H cross-coupling of indoles/pyrroles with heteroarenes
Co-reporter:Xurong Qin, Hu Liu, Dekun Qin, Qian Wu, Jingsong You, Dongbing Zhao, Qiang Guo, Xiaolei Huang and Jingbo Lan  
Chemical Science 2013 vol. 4(Issue 5) pp:1964-1969
Publication Date(Web):18 Jan 2013
DOI:10.1039/C3SC22241A
The chelation-assisted strategy has been endowed with some novel functions in the Rh(III)-catalyzed dehydrogenative coupling of indoles/pyrroles with heteroarenes. While the reaction conditions used are rather common, the strategy can close the homo-coupling pathway of each coupling partner, and dramatically extend substrate scope along with the exclusive indole or pyrrole C2-site selectivity. This is the first example describing that a catalytic system allows the oxidative C–H/C–H hetero-coupling not only between two electron-rich heteroarenes but also between electron-deficient and electron-rich heteroarenes, showing a further beneficial aspect of the Rh(III) catalysis.
2-Pyridylmethyl ether: a readily removable and efficient directing group for amino acid ligand accelerated ortho-C–H olefination of phenols
Co-reporter:Xuefeng Cong, Jingsong You, Ge Gao and Jingbo Lan  
Chemical Communications 2013 vol. 49(Issue 7) pp:662-664
Publication Date(Web):05 Nov 2012
DOI:10.1039/C2CC37291F
2-Pyridylmethyl ether-directed ortho-C–H olefination of phenols via a seven-membered cyclopalladated intermediate has been disclosed to construct a variety of ortho-alkenyl phenols and ortho-alkyl phenols.
Copper-catalysed oxidative C–H/N–H cross-coupling between formamides and amides through chelation-assisted N–H activation
Co-reporter:Xiaoyu Li, Bijin Li, Jingsong You and Jingbo Lan  
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 12) pp:1925-1928
Publication Date(Web):01 Feb 2013
DOI:10.1039/C3OB40094H
A copper-catalysed oxidative C–H/N–H cross-coupling between formamides and amides through chelation-assisted N–H activation has been developed for the preparation of various multi-substituted ureas.
Palladium-catalyzed tandem N–H/C–H arylation: regioselective synthesis of N-heterocycle-fused phenanthridines as versatile blue-emitting luminophores
Co-reporter:Lipeng Yan, Dongbing Zhao, Jingbo Lan, Yangyang Cheng, Qiang Guo, Xiaoyu Li, Ningjie Wu and Jingsong You  
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 45) pp:7966-7977
Publication Date(Web):30 Sep 2013
DOI:10.1039/C3OB41760C
A general and highly regioselective synthetic protocol for structurally diverse N-heteroaryl-fused phenanthridines has been developed. Varieties of fluorescence molecules comprising imidazole-fused, benzoimidazole-fused, indole-fused and pyrrole-fused phenanthridines were obtained by this modular approach, some of which exhibit excellent blue-emitting performance, high quantum yields, long fluorescence lifetimes, interesting electrochemical properties, and thermal stabilities.
Direct arylation of phenanthroline derivatives via oxidative C–H/C–H cross-coupling: synthesis and discovery of excellent ligands
Co-reporter:Bijin Li, Xurong Qin, Jingsong You, Xuefeng Cong and Jingbo Lan  
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 8) pp:1290-1293
Publication Date(Web):20 Dec 2012
DOI:10.1039/C2OB27325J
A concise synthetic protocol for aryl functionalized phenanthrolines has been developed. It was demonstrated that 3,8-diphenyl-1,10-phenanthroline (7a) is competent in promoting transition-metal-free direct arylation and 2,3,8,9-tetraphenyl-1,10-phenanthroline (8a) is a highly efficient ligand in the in situ Pd-catalysed Heck reaction.
Copper(II)-Catalyzed Dehydrogenative Cross-Coupling between Two Azoles
Co-reporter:Xurong Qin, Boya Feng, Jiaxing Dong, Xiaoyu Li, Ying Xue, Jingbo Lan, and Jingsong You
The Journal of Organic Chemistry 2012 Volume 77(Issue 17) pp:7677-7683
Publication Date(Web):August 17, 2012
DOI:10.1021/jo301128y
The copper(II)-catalyzed dehydrogenative coupling between two different azoles for the preparation of unsymmetrical biazoles has been developed. The current catalytic system can effectively control the chemoselectivity for heterocoupling over homocoupling.
One-pot synthesis of benzofused heteroaryl azoles via tandem C-heteroatom coupling/C–H activation of azoles
Co-reporter:Xurong Qin, Xuefeng Cong, Dongbing Zhao, Jingsong You and Jingbo Lan  
Chemical Communications 2011 vol. 47(Issue 19) pp:5611-5613
Publication Date(Web):08 Apr 2011
DOI:10.1039/C1CC10572H
The Cu(I) or Pd(II)-catalyzed cross-couplings of gem-dihaloolefins with azoles via tandem C-heteroatom coupling/C–H activation for the preparation of benzofused heteroaryl azoles have been developed.
Cyclen-functionalized perylenebisimides as sensitive and selective fluorescent sensors for Pb2+ in aqueous solution
Co-reporter:Rongqi Zhou, Bijin Li, Ningjie Wu, Ge Gao, Jingsong You and Jingbo Lan  
Chemical Communications 2011 vol. 47(Issue 23) pp:6668-6670
Publication Date(Web):11 May 2011
DOI:10.1039/C1CC11200G
Cyclen-functionalized perylenediimides PBI-1 and PBI-2 were first synthesized as highly sensitive and selective fluorescent chemosensors for Pb2+ in aqueous solution. PBI-2 shows a better selectivity for Pb2+ in the presence of other metal ions and, importantly, it can successfully enter the cell and be applied in imaging of living cells.
1,1′-Binaphthyl-based imidazolium chemosensors for highly selective recognition of tryptophan in aqueous solutions
Co-reporter:Li Yang, Song Qin, Xiaoyu Su, Fei Yang, Jingsong You, Changwei Hu, Rugang Xie and Jingbo Lan  
Organic & Biomolecular Chemistry 2010 vol. 8(Issue 2) pp:339-348
Publication Date(Web):17 Nov 2009
DOI:10.1039/B908540H
A type of 1,1′-binaphthyl-based imidazolium chemosensor module has been synthesized for the highly selective recognition of tryptophan (Trp) among the eleven α-amino acids investigated in aqueous solutions via synergistic effects of multiple hydrogen bonding and electrostatic interactions. These results have demonstrated that the C-2 hydrogen atom of the imidazolium ring plays a key role as a hydrogen bond donor. The UV/vis, fluorescence and mass spectral studies have indicated that a 1:1 complex is formed between the host and tryptophan. The binding affinity and selectivity of the cleft-like receptor (R)-1 with L-Trp are superior to those of (R)-2–5. In spite of an inferior selectivity towards various aromatic amino acids, the macrocyclic (R)-3 displays a remarkable enantiodiscrimination for the two enantiomers of tryptophan with a KD/KL value as high as 6.2.
Squaraine-based colorimetric and fluorescent sensors for Cu2+-specific detection and fluorescence imaging in living cells
Co-reporter:Weida Wang, Afu Fu, Jingsong You, Ge Gao, Jingbo Lan, Lijuan Chen
Tetrahedron 2010 66(21) pp: 3695-3701
Publication Date(Web):
DOI:10.1016/j.tet.2010.03.070
Enantioselective recognitions of chiral molecular tweezers containing imidazoliums for amino acids
Co-reporter:Xiaoyu Su;Kui Luo;Qingxiang Xiang;Rugang Xie
Chirality 2009 Volume 21( Issue 5) pp:539-546
Publication Date(Web):
DOI:10.1002/chir.20635

Abstract

Two kinds of novel chiral molecular tweezers containing imidazoliums were synthesized from L-alanine, L-phenylalanine, and L-glutamic acid. They are constructed by the chiral imidazolium pincers and two different spacers which are 1,3-bis (bromomethyl)benzene and 2,6-bis(bromomethyl)pyridine, respectively. The enantioselective recognition of L- and D-amino acid derivatives by these molecular tweezers was investigated by UV spectroscopic titration experiments and good enantioselectivities were obtained, which are highly sensitive to whether the spacer has the binding site and the pincers has the other aromatic rings besides imidazolium ring. The host molecular 3b.2PF6− showed remarkable enantioselectivity for N-Boc protected histidine methyl ester, affording KL/KD of 5.10. Chirality, 2009. © 2008 Wiley-Liss, Inc.

Copper-catalysed oxidative C–H/N–H cross-coupling between formamides and amides through chelation-assisted N–H activation
Co-reporter:Xiaoyu Li, Bijin Li, Jingsong You and Jingbo Lan
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 12) pp:NaN1928-1928
Publication Date(Web):2013/02/01
DOI:10.1039/C3OB40094H
A copper-catalysed oxidative C–H/N–H cross-coupling between formamides and amides through chelation-assisted N–H activation has been developed for the preparation of various multi-substituted ureas.
Palladium-catalyzed tandem N–H/C–H arylation: regioselective synthesis of N-heterocycle-fused phenanthridines as versatile blue-emitting luminophores
Co-reporter:Lipeng Yan, Dongbing Zhao, Jingbo Lan, Yangyang Cheng, Qiang Guo, Xiaoyu Li, Ningjie Wu and Jingsong You
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 45) pp:NaN7977-7977
Publication Date(Web):2013/09/30
DOI:10.1039/C3OB41760C
A general and highly regioselective synthetic protocol for structurally diverse N-heteroaryl-fused phenanthridines has been developed. Varieties of fluorescence molecules comprising imidazole-fused, benzoimidazole-fused, indole-fused and pyrrole-fused phenanthridines were obtained by this modular approach, some of which exhibit excellent blue-emitting performance, high quantum yields, long fluorescence lifetimes, interesting electrochemical properties, and thermal stabilities.
Rh-catalysed direct cyclisation of 1,4-naphthoquinone and 9,10-phenanthraquinone with alkyne: facile access to 1,8-dioxapyrenes and 1,12-dioxaperylenes as orange and red-emitting luminophores
Co-reporter:Jing Wang, Dekun Qin, Jingbo Lan, Yangyang Cheng, Shuai Zhang, Qiang Guo, Jie Wu, Di Wu and Jingsong You
Chemical Communications 2015 - vol. 51(Issue 29) pp:NaN6339-6339
Publication Date(Web):2015/03/03
DOI:10.1039/C5CC00312A
Rh-catalysed direct cyclisation of 1,4-naphthoquinones and 9,10-phenanthraquinones with alkynes has been accomplished for the first time through the C–H activation strategy to forge 1,8-dioxapyrenes and 1,12-dioxaperylenes. Starting from readily available substrates, a variety of dipyran-containing PAHs are obtained in one step and exhibit orange/red-emitting performance, large Stokes shifts and high thermal stability.
Chelation-assisted Pd-catalysed ortho-selective oxidative C–H/C–H cross-coupling of aromatic carboxylic acids with arenes and intramolecular Friedel–Crafts acylation: one-pot formation of fluorenones
Co-reporter:Denan Sun, Bijin Li, Jingbo Lan, Quan Huang and Jingsong You
Chemical Communications 2016 - vol. 52(Issue 18) pp:NaN3638-3638
Publication Date(Web):2016/01/28
DOI:10.1039/C6CC00103C
Pd-Catalysed ortho-selective oxidative C–H/C–H cross-coupling of aromatic carboxylic acids with arenes and subsequent intramolecular Friedel–Crafts acylation has been accomplished for the first time through a chelation-assisted C–H activation strategy. Starting from the readily available substrates, a variety of fluorenone derivatives are obtained in one pot. The direct use of naturally occurring carboxylic acid functionalities as directing groups avoids unnecessary steps for installation and removal of an extra directing group.
Direct arylation of phenanthroline derivatives via oxidative C–H/C–H cross-coupling: synthesis and discovery of excellent ligands
Co-reporter:Bijin Li, Xurong Qin, Jingsong You, Xuefeng Cong and Jingbo Lan
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 8) pp:NaN1293-1293
Publication Date(Web):2012/12/20
DOI:10.1039/C2OB27325J
A concise synthetic protocol for aryl functionalized phenanthrolines has been developed. It was demonstrated that 3,8-diphenyl-1,10-phenanthroline (7a) is competent in promoting transition-metal-free direct arylation and 2,3,8,9-tetraphenyl-1,10-phenanthroline (8a) is a highly efficient ligand in the in situ Pd-catalysed Heck reaction.
1,1′-Binaphthyl-based imidazolium chemosensors for highly selective recognition of tryptophan in aqueous solutions
Co-reporter:Li Yang, Song Qin, Xiaoyu Su, Fei Yang, Jingsong You, Changwei Hu, Rugang Xie and Jingbo Lan
Organic & Biomolecular Chemistry 2010 - vol. 8(Issue 2) pp:NaN348-348
Publication Date(Web):2009/11/17
DOI:10.1039/B908540H
A type of 1,1′-binaphthyl-based imidazolium chemosensor module has been synthesized for the highly selective recognition of tryptophan (Trp) among the eleven α-amino acids investigated in aqueous solutions via synergistic effects of multiple hydrogen bonding and electrostatic interactions. These results have demonstrated that the C-2 hydrogen atom of the imidazolium ring plays a key role as a hydrogen bond donor. The UV/vis, fluorescence and mass spectral studies have indicated that a 1:1 complex is formed between the host and tryptophan. The binding affinity and selectivity of the cleft-like receptor (R)-1 with L-Trp are superior to those of (R)-2–5. In spite of an inferior selectivity towards various aromatic amino acids, the macrocyclic (R)-3 displays a remarkable enantiodiscrimination for the two enantiomers of tryptophan with a KD/KL value as high as 6.2.
One-pot synthesis of benzofused heteroaryl azoles via tandem C-heteroatom coupling/C–H activation of azoles
Co-reporter:Xurong Qin, Xuefeng Cong, Dongbing Zhao, Jingsong You and Jingbo Lan
Chemical Communications 2011 - vol. 47(Issue 19) pp:NaN5613-5613
Publication Date(Web):2011/04/08
DOI:10.1039/C1CC10572H
The Cu(I) or Pd(II)-catalyzed cross-couplings of gem-dihaloolefins with azoles via tandem C-heteroatom coupling/C–H activation for the preparation of benzofused heteroaryl azoles have been developed.
2-Pyridylmethyl ether: a readily removable and efficient directing group for amino acid ligand accelerated ortho-C–H olefination of phenols
Co-reporter:Xuefeng Cong, Jingsong You, Ge Gao and Jingbo Lan
Chemical Communications 2013 - vol. 49(Issue 7) pp:NaN664-664
Publication Date(Web):2012/11/05
DOI:10.1039/C2CC37291F
2-Pyridylmethyl ether-directed ortho-C–H olefination of phenols via a seven-membered cyclopalladated intermediate has been disclosed to construct a variety of ortho-alkenyl phenols and ortho-alkyl phenols.
Cu-catalysed oxidative C–H/C–H coupling polymerisation of benzodiimidazoles: an efficient approach to regioregular polybenzodiimidazoles for blue-emitting materials
Co-reporter:Quan Huang, Xurong Qin, Bijin Li, Jingbo Lan, Qiang Guo and Jingsong You
Chemical Communications 2014 - vol. 50(Issue 89) pp:NaN13741-13741
Publication Date(Web):2014/09/15
DOI:10.1039/C4CC06291D
The Cu-catalysed oxidative C–H/C–H coupling reaction of azoles has been used for the first time to develop polymerisation, which provides an efficient method for the preparation of polybenzodiimidazoles. These polymers exhibit high molecular weights, regioregularity, blue-emitting performance and thermal stability.
Cyclen-functionalized perylenebisimides as sensitive and selective fluorescent sensors for Pb2+ in aqueous solution
Co-reporter:Rongqi Zhou, Bijin Li, Ningjie Wu, Ge Gao, Jingsong You and Jingbo Lan
Chemical Communications 2011 - vol. 47(Issue 23) pp:NaN6670-6670
Publication Date(Web):2011/05/11
DOI:10.1039/C1CC11200G
Cyclen-functionalized perylenediimides PBI-1 and PBI-2 were first synthesized as highly sensitive and selective fluorescent chemosensors for Pb2+ in aqueous solution. PBI-2 shows a better selectivity for Pb2+ in the presence of other metal ions and, importantly, it can successfully enter the cell and be applied in imaging of living cells.
Stoichiometric to catalytic reactivity of the aryl cycloaurated species with arylboronic acids: insight into the mechanism of gold-catalyzed oxidative C(sp2)–H arylation
Co-reporter:Qian Wu, Chenglong Du, Yumin Huang, Xingyan Liu, Zhen Long, Feijie Song and Jingsong You
Chemical Science (2010-Present) 2015 - vol. 6(Issue 1) pp:NaN293-293
Publication Date(Web):2014/10/09
DOI:10.1039/C4SC02070G
Based on the well-defined five-membered aryl gold(III) complexes, [Au(tpy)X2] (3a and 3b) and [AuBr(Ph)(tpy)] (7), as well as the aryl gold(III) complex [AuCl2(Ph)(tpy)] (8) (tpy = 2-(o-tolyl)pyridine) as reliable models, we present a detailed study of the mechanism for gold(III)-catalyzed oxidative cross-coupling reactions between cycloaurable arenes and arylboronic acids. Here we report the direct evidence for a mechanistic proposal including arene C–H activation, transmetallation and biaryl reductive elimination. The chelation-assisted C–H activation strategy has been used for the development of the gold(III)-catalyzed C–H bond arylation of arenes with aryl reagents to forge extended π-conjugated systems.
Chelation-assisted Rh(III)-catalyzed C2-selective oxidative C–H/C–H cross-coupling of indoles/pyrroles with heteroarenes
Co-reporter:Xurong Qin, Hu Liu, Dekun Qin, Qian Wu, Jingsong You, Dongbing Zhao, Qiang Guo, Xiaolei Huang and Jingbo Lan
Chemical Science (2010-Present) 2013 - vol. 4(Issue 5) pp:NaN1969-1969
Publication Date(Web):2013/01/18
DOI:10.1039/C3SC22241A
The chelation-assisted strategy has been endowed with some novel functions in the Rh(III)-catalyzed dehydrogenative coupling of indoles/pyrroles with heteroarenes. While the reaction conditions used are rather common, the strategy can close the homo-coupling pathway of each coupling partner, and dramatically extend substrate scope along with the exclusive indole or pyrrole C2-site selectivity. This is the first example describing that a catalytic system allows the oxidative C–H/C–H hetero-coupling not only between two electron-rich heteroarenes but also between electron-deficient and electron-rich heteroarenes, showing a further beneficial aspect of the Rh(III) catalysis.
Cu-catalysed direct C–H (hetero)arylation of [1,2,4]triazolo[4,3-a]pyridine to construct deep-blue-emitting luminophores
Co-reporter:Jie Wu, Qiulin You, Jingbo Lan, Qiang Guo, Xiaoyu Li, Ying Xue and Jingsong You
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 19) pp:NaN5375-5375
Publication Date(Web):2015/04/07
DOI:10.1039/C5OB00552C
Cu-catalysed direct C–H (hetero)arylation of [1,2,4]triazolo[4,3-a]pyridine has been accomplished for the first time to streamline the synthesis of 3-aryl-[1,2,4]triazolo[4,3-a]pyridines for screening blue-emitting materials. On this basis, the photophysical properties of the resulting compounds were systematically investigated, most of which exhibited excellent deep-blue emission with moderate to high quantum yields, photostability, air stability and thermal stability.
A sensitive colorimetric and fluorescent sensor based on imidazolium-functionalized squaraines for the detection of GTP and alkaline phosphatase in aqueous solution
Co-reporter:Ningjie Wu, Jingbo Lan, Lipeng Yan and Jingsong You
Chemical Communications 2014 - vol. 50(Issue 34) pp:NaN4441-4441
Publication Date(Web):2014/03/04
DOI:10.1039/C4CC00752B
Imidazolium-functionalized squaraine ImSQ8 is synthesized as a sensitive colorimetric and fluorescent chemosensor for GTP in aqueous solution. The detection limit of GTP reaches 5.4 ppb. Its applications in the live-cell imaging and enzyme activity assay have also been demonstrated.
Acetic acid, [(4-methylphenyl)thio][(4-nitrobenzoyl)oxy]-, ethyl ester, (-)-
Acetic acid, [(4-methylphenyl)thio][(4-nitrobenzoyl)oxy]-, ethyl ester, (-)-
CAS:188488-85-9
Acetic acid, [(4-methylphenyl)thio][(4-nitrobenzoyl)oxy]-, ethyl ester, (-)-
2-METHYLINDAZOLE-5-CARBALDEHYDE
2-METHYLINDAZOLE-5-CARBALDEHYDE
CAS:1266558-20-6
2-METHYLINDAZOLE-5-CARBALDEHYDE
1-(2-METHYLINDAZOL-5-YL)ETHANONE
1-(2-METHYLINDAZOL-5-YL)ETHANONE
CAS:1159511-28-0
1-(2-METHYLINDAZOL-5-YL)ETHANONE
CAS:1046416-34-5
Benzo[1,2-b:4,5-b']dithiophene, 4,8-bis(dodecyloxy)-
Benzo[1,2-b:4,5-b']dithiophene, 4,8-bis(dodecyloxy)-
CAS:1044795-04-1
Benzo[1,2-b:4,5-b']dithiophene, 4,8-bis(dodecyloxy)-
3,3'-(5'-(3-(Pyridin-3-yl)phenyl)-[1,1':3',1''-terphenyl]-3,3''-diyl)dipyridine
3,3'-(5'-(3-(Pyridin-3-yl)phenyl)-[1,1':3',1''-terphenyl]-3,3''-diyl)dipyridine
CAS:921205-03-0
3,3'-(5'-(3-(Pyridin-3-yl)phenyl)-[1,1':3',1''-terphenyl]-3,3''-diyl)dipyridine
2H-Indazol-5-amine, N,N,2-trimethyl-
2H-Indazol-5-amine, N,N,2-trimethyl-
CAS:918903-51-2
2H-Indazol-5-amine, N,N,2-trimethyl-
1H-ISOINDOLE-1,3(2H)-DIONE, 2-(4-FLUOROPHENOXY)-
1H-ISOINDOLE-1,3(2H)-DIONE, 2-(4-FLUOROPHENOXY)-
CAS:880473-80-3
1H-ISOINDOLE-1,3(2H)-DIONE, 2-(4-FLUOROPHENOXY)-
2-Butenoic acid, 3-(phenylamino)-, 1,1-dimethylethyl ester, (2Z)-
2-Butenoic acid, 3-(phenylamino)-, 1,1-dimethylethyl ester, (2Z)-
CAS:859231-95-1
2-Butenoic acid, 3-(phenylamino)-, 1,1-dimethylethyl ester, (2Z)-
2-Butenoic acid, 3-[(phenylmethyl)amino]-, phenylmethyl ester, (2Z)-
2-Butenoic acid, 3-[(phenylmethyl)amino]-, phenylmethyl ester, (2Z)-
CAS:765911-06-6
2-Butenoic acid, 3-[(phenylmethyl)amino]-, phenylmethyl ester, (2Z)-