Carbazole-Based Boron Dipyrromethenes (BODIPYs): Facile Synthesis, Structures, and Fine-Tunable Optical Properties

被引：56

作者：

Maeda, Chihiro ^{[1
]}

Todaka, Takumi ^{[1
]}

Ema, Tadashi ^{[1
]}

机构：

[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Chem & Biotechnol, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 12期

关键词：

AZA-BODIPY; FUSED BODIPY; FLUORESCENT DYES; CATALYZED BORYLATION; HIGHLY FLUORESCENT; OLIGOMERS; BRIGHT; RED; FUNCTIONALIZATION; PORPHYRINOIDS;

D O I：

10.1021/acs.orglett.5b01363

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbazole-based BODIPYs were synthesized in three steps using an organometallic approach consisting of sequential Ir-catalyzed borylation, Suzuki-Miyaura coupling, and boron complexation. Various substituents were introduced into the carbazole moiety, and large substituent effects were confirmed by means of absorption spectroscopy, cyclic voltammetry, and DFT calculations. Dibenzocarbazoles were also converted into the corresponding BODIPYs.

引用

页码：3090 / 3093

页数：4

共 64 条

[1] Sulfur-Bridged BODIPY DYEmers [J].

Ahrens, Johannes ;

Boeker, Birte ;

Brandhorst, Kai ;

Funk, Markus ;

Broering, Martin .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (34) :11382-11395

[2] High Stokes Shift Anilido-Pyridine Boron Difluoride Dyes [J].

Araneda, Juan F. ;

Piers, Warren E. ;

Heyne, Belinda ;

Parvez, Masood ;

McDonald, Robert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (51) :12214-12217

[3] Singlet Oxygen Generation by Novel NIR BODIPY Dyes [J].

Awuah, Samuel G. ;

Polreis, Jason ;

Biradar, Vidya ;

You, Youngjae .

ORGANIC LETTERS, 2011, 13 (15) :3884-3887

[4] Design, synthesis and photophysical studies of dipyrromethene-based materials: insights into their applications in organic photovoltaic devices [J].

Bessette, Andre ;

Hanan, Garry S. .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (10) :3342-3405

[5] A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds [J].

Billingsley, Kelvin L. ;

Anderson, Kevin W. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (21) :3484-3488

[6] NIR-fluorescent coumarin-fused BODIPY dyes with large Stokes shifts [J].

Bochkov, Andrei Y. ;

Akchurin, Igor O. ;

Dyachenko, Oleg A. ;

Traven, Valery F. .

CHEMICAL COMMUNICATIONS, 2013, 49 (99) :11653-11655

[7] Fluorescent indicators based on BODIPY [J].

Boens, Noel ;

Leen, Volker ;

Dehaen, Wim .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) :1130-1172

[8] Phenylethynyl-BODIPY Oligomers: Bright Dyes and Fluorescent Building Blocks [J].

Cakmak, Yusuf ;

Akkaya, Engin U. .

ORGANIC LETTERS, 2009, 11 (01) :85-88

[9] 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes modified for extended conjugation and restricted bond rotations [J].

Chen, J ;

Burghart, A ;

Derecskei-Kovacs, A ;

Burgess, K .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :2900-2906

[10] Diversity-Oriented Facile Access to Highly Fluorescent Membrane-Permeable Benz[c,d]indole N-Heteroarene BF2 Dyes [J].

Cheng, Chi ;

Gao, Naixun ;

Yu, Changjiang ;

Wang, Zhaoyun ;

Wang, Jun ;

Hao, Erhong ;

Wei, Yun ;

Mu, Xiaolong ;

Tian, Yanli ;

Ran, Chongzhao ;

Jiao, Lijuan .

ORGANIC LETTERS, 2015, 17 (02) :278-281

← 1 2 3 4 5 6 7 →