Extended conjugated borenium dimers via late stage functionalization of air-stable borepinium ions

被引:28
作者
Adachi, Yohei [1 ,2 ]
Arai, Fuka [1 ]
Jakle, Frieder [2 ]
机构
[1] Hiroshima Univ, Grad Sch Engn, Dept Appl Chem, Higashihiroshima 7398527, Japan
[2] Rutgers Univ Newark, Dept Chem, 73 Warren St, Newark, NJ 07102 USA
关键词
N-HETEROCYCLIC CARBENE; POLYCYCLIC AROMATICS; ELECTRON-DEFICIENT; BORON; TRIARYLBORANE; MOLECULES; POLYMERS; ACCEPTOR; ROUTE;
D O I
10.1039/d0cc02514c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Applications of highly electron-deficient organoborenium ions in conjugated materials remain scarce due to their low stability toward air and moisture. We report here the preparation of benzo[d]dithieno[b,f]borepinium ions as air-stable pi-conjugated heterocycles and their conversion into the first dimeric borenium cations, which exhibit very low lying LUMOs and enhanced fluorescence as a result of extended conjugation.
引用
收藏
页码:5119 / 5122
页数:4
相关论文
共 43 条
[1]   Synthesis and Properties of Benzo[d]dithieno[b,f]borepins [J].
Adachi, Yohei ;
Ohshita, Joji .
ORGANOMETALLICS, 2018, 37 (06) :869-881
[2]   Hybrid conjugated polymers with alternating dithienosilole or dithienogermole and tricoordinate boron units [J].
Adachi, Yohei ;
Ooyama, Yousuke ;
Ren, Yi ;
Yin, Xiaodong ;
Jakle, Frieder ;
Ohshita, Joji .
POLYMER CHEMISTRY, 2018, 9 (03) :291-299
[3]   A Poly(9-Borafluorene) Homopolymer: An Electron-Deficient Polyfluorene with "Turn-On" Fluorescence Sensing of NH3 Vapor [J].
Adams, Ian A. ;
Rupar, Paul A. .
MACROMOLECULAR RAPID COMMUNICATIONS, 2015, 36 (14) :1336-1340
[4]   Quantum Interference Enhanced Chemical Responsivity in Single-Molecule Dithienoborepin Junctions [J].
Baghernejad, Masoud ;
Van Dyck, Colin ;
Bergfield, Justin ;
Levine, David R. ;
Gubicza, Agnes ;
Tovar, John D. ;
Calame, Michel ;
Broekmann, Peter ;
Hong, Wenjing .
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (66) :15141-15146
[5]   Synthesis and Luminescent Properties of Lewis Base-Appended Borafluorenes [J].
Berger, Christopher J. ;
He, Gang ;
Merten, Christian ;
McDonald, Robert ;
Ferguson, Michael J. ;
Rivard, Eric .
INORGANIC CHEMISTRY, 2014, 53 (03) :1475-1486
[6]   Conjugated "B-Entacenes": Polycyclic Aromatics Containing Two Borepin Rings [J].
Caruso, Anthony, Jr. ;
Tovar, John D. .
ORGANIC LETTERS, 2011, 13 (12) :3106-3109
[7]   Functionalized Dibenzoborepins as Components of Small Molecule and Polymeric π-Conjugated Electronic Materials [J].
Caruso, Anthony, Jr. ;
Tovar, John D. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07) :2227-2239
[8]   Synthesis of Functionalizable Boron-Containing π-Electron Materials that Incorporate Formally Aromatic Fused Borepin Rings [J].
Caruso, Anthony, Jr. ;
Siegler, Maxime A. ;
Tovar, John D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (25) :4213-4217
[9]   Cationic Tricoordinate Boron Intermediates: Borenium Chemistry from the Organic Perspective [J].
De Vries, Timothy S. ;
Prokofjevs, Aleksandrs ;
Vedejs, Edwin .
CHEMICAL REVIEWS, 2012, 112 (07) :4246-4282
[10]   N-Heterocyclic Carbene Adducts of Main Group Elements and Their Use as Ligands in Transition Metal Chemistry [J].
Doddi, Adinarayana ;
Peters, Marius ;
Tamm, Matthias .
CHEMICAL REVIEWS, 2019, 119 (12) :6994-7112