Adapting N-Heterocyclic Carbene/Azide Coupling Chemistry for Polymer Synthesis: Enabling Access to Aromatic Polytriazenes

被引:72
作者
Coady, Daniel J. [1 ]
Khramov, Dimitri M. [1 ]
Norris, Brent C. [1 ]
Tennyson, Andrew G. [1 ]
Bielawski, Christopher W. [1 ]
机构
[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
azides; carbenes; click chemistry; coupling reactions; polymers; AZA-WITTIG POLYMERIZATION; CLICK-CHEMISTRY; THIN-FILMS; ELECTRONIC-STRUCTURE; POLYAZOMETHINES; AZIDES; ETHER; POLY(AZOMETHINE); POLYAZINES; TRIAZENES;
D O I
10.1002/anie.200901046
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A click by any other name: Coupling bis(N-heterocyclic carbene)s with bis(azide)s afforded a novel class of conjugated polytriazenes. These polymers were rendered electrically conductive upon doping, and fluorene-containing variants exhibited luminescence. This adaptation of Nheterocyclic carbene (NHC)/azide coupling chemistry to polymer synthesis reveals the potential of NHCs as building blocks for accessing polymers having useful electronic properties. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5187 / 5190
页数:4
相关论文
共 70 条
[1]   Contribution to the structure of benzidine [J].
Adams, R ;
Bullock, JE ;
Wilson, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1923, 45 :521-527
[2]   Looking for stable carbenes: The difficulty in starting anew [J].
Arduengo, AJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) :913-921
[3]   POLYETHER AZOMETHINES .1. SYNTHESIS AND CHARACTERIZATION [J].
BANERJEE, S ;
GUTCH, PK ;
SAXENA, C .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1995, 33 (10) :1719-1725
[4]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[5]   A modular approach to main-chain organometallic polymers [J].
Boydston, AJ ;
Williams, KA ;
Bielawski, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (36) :12496-12497
[6]   Bis(imidazolylidene)s as modular building blocks for monomeric and macromolecular organometallic materials [J].
Boydston, Andrew J. ;
Bielawski, Christopher W. .
DALTON TRANSACTIONS, 2006, (34) :4073-4077
[7]   Organic azides:: An exploding diversity of a unique class of compounds [J].
Bräse, S ;
Gil, C ;
Knepper, K ;
Zimmermann, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240
[8]  
Brase S., 2005, ANGEW CHEM, V117, P5320, DOI DOI 10.1002/ANGE.200400657
[9]   Photopolymerization of reactive mesogenic Schiff bases and related metallomesogens [J].
Cano, M ;
Oriol, L ;
Piñol, M ;
Serrano, JL .
CHEMISTRY OF MATERIALS, 1999, 11 (01) :94-100
[10]   Mechanical properties and characterization of the crystalline structure in annealed thermotropic poly(azomethines) [J].
Cerrada, P ;
Oriol, L ;
Pinol, M ;
Serrano, JL ;
Iribarren, I ;
Guerra, SM .
MACROMOLECULES, 1996, 29 (07) :2515-2523