Synthesis, Properties, and Semiconducting Characteristics of BF2 Complexes of β,β-Bisphenanthrene-Fused Azadipyrromethenes

被引:61
作者
Sheng, Wanle [1 ]
Zheng, Yu-Qing [2 ]
Wu, Qinghua [1 ]
Wu, Yayang [1 ]
Yu, Changjiang [1 ]
Jiao, Lijuan [1 ]
Hao, Erhong [1 ]
Wang, Jie-Yu [2 ]
Pei, Jian [2 ]
机构
[1] Anhui Normal Univ, Lab Funct Mol Solids, Minist Educ, Sch Chem & Mat Sci, Wuhu 241000, Peoples R China
[2] Peking Univ, Beijing Natl Lab Mol Sci, Coll Chem & Mol Engn, Beijing 100080, Peoples R China
关键词
FIELD-EFFECT TRANSISTORS; THIN-FILM TRANSISTORS; NEAR-INFRARED DYES; BODIPY DYES; SOLAR-CELLS; AZA-BODIPY; CONJUGATED POLYMERS; DIPOLE INTERACTIONS; FUSED BODIPYS; FAR-RED;
D O I
10.1021/acs.orglett.7b01133
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three novel Pi-extended BF2 complexes of beta,beta-bisphenanthrene fused azadipyrromethenes containing nine fused, rings have been synthesized on the basis of a tandem. Suzuki coupling reaction on reaction on available 2,6-dibromoazaBODIPYs followed by an intramolecular oxidative aromatic Coupling mediated by iron(III) Chloride. These, resultant BF2 complexes exhibit strong absorption (extinction coefficients up to 2.4 x 10(5) M-1 cm(-1) and emission in the near-infrared (NIR) range (790-816 nm) with excellent photo and thermal stabilities. The hole Mobility of the thin-filin field-effect trahsistors of these dyes fabricated by :a solution process. reaches up to 0.018 cm(2) V-1 s(-1).
引用
收藏
页码:2893 / 2896
页数:4
相关论文
共 76 条
[1]   Near-Infrared Nitrofluorene Substitued Aza-Boron-dipyrromethenes Dyes [J].
Bellier, Quenlin ;
Pegaz, Sarah ;
Aronica, Christophe ;
Le Guennic, Boris ;
Andraud, Chantal ;
Maury, Olivier .
ORGANIC LETTERS, 2011, 13 (01) :22-25
[2]   Thiophene-substituted aza-bodipy as a strategic synthon for the design of near-infrared dyes [J].
Bellier, Quentin ;
Dalier, Fabrice ;
Jeanneau, Erwann ;
Maury, Olivier ;
Andraud, Chantal .
NEW JOURNAL OF CHEMISTRY, 2012, 36 (03) :768-773
[3]   A fluorescence off-on reporter for real time monitoring of gemcitabine delivery to the cancer cells [J].
Bhuniya, Sankarprasad ;
Lee, Min Hee ;
Jeon, Hyun Mi ;
Han, Ji Hye ;
Lee, Jae Hong ;
Park, Nayoung ;
Maiti, Sukhendu ;
Kang, Chulhun ;
Kim, Jong Seung .
CHEMICAL COMMUNICATIONS, 2013, 49 (64) :7141-7143
[4]   Fluorescent indicators based on BODIPY [J].
Boens, Noel ;
Leen, Volker ;
Dehaen, Wim .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) :1130-1172
[5]   High-Performance Solution-Processed Solar Cells and Ambipolar Behavior in Organic Field-Effect Transistors with Thienyl-BODIPY Scaffoldings [J].
Bura, Thomas ;
Leclerc, Nicolas ;
Fall, Sadiara ;
Leveque, Patrick ;
Heiser, Thomas ;
Retailleau, Pascal ;
Rihn, Sandra ;
Mirloup, Antoine ;
Ziessel, Raymond .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) :17404-17407
[6]   Large π-Conjugated Quinacridone Derivatives: Syntheses, Characterizations, Emission, and Charge Transport Properties [J].
Chen, Weiping ;
Tian, Kui ;
Song, Xiaoxian ;
Zhang, Zuolun ;
Ye, Kaiqi ;
Yu, Gui ;
Wang, Yue .
ORGANIC LETTERS, 2015, 17 (24) :6146-6149
[7]   Heterotriangulenes π-Expanded at Bridging Positions [J].
Chou, Chih-Ming ;
Saito, Shohei ;
Yamaguchi, Shigehiro .
ORGANIC LETTERS, 2014, 16 (11) :2868-2871
[8]   Unusual Intramolecular Hydrogen Transfer in 3,5-Di(triphenylethylenyl) BODIPY Synthesis and 1,2-Migratory Shift in Subsequent Scholl Type Reaction [J].
Chua, Ming Hui ;
Huang, Kuo-Wei ;
Xu, Jianwei ;
Wu, Jishan .
ORGANIC LETTERS, 2015, 17 (17) :4168-4171
[9]   Bis(2-pyridyl)-substituted boratriazaindacene as an NIR-emitting chemosensor for Hg(II) [J].
Coskun, Ali ;
Yilmaz, M. Deniz ;
Akkaya, Engin U. .
ORGANIC LETTERS, 2007, 9 (04) :607-609
[10]   Synthesis, Optoelectronic, and Transistor Properties of BODIPY- and Cyclopenta[c]thiophene-Containing π-Conjugated Copolymers [J].
Debnath, Sashi ;
Singh, Saumya ;
Bedi, Anjan ;
Krishnamoorthy, Kothandam ;
Zade, Sanjio S. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2015, 119 (28) :15859-15867