Structurally Dynamic Materials Based on Bis(N-heterocyclic carbene)s and Bis(isothiocyanate)s: Toward Reversible, Conjugated Polymers

被引:59
作者
Norris, Brent C. [1 ]
Bielawski, Christopher W. [1 ]
机构
[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
COVALENT POLYMERS; CHEMISTRY; ISOTHIOCYANATES;
D O I
10.1021/ma100524g
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A study was conducted to demonstrate the formation of structurally dynamic materials based on bis(N-heterocyclic carbene)s (NHC) and bis(isothiocyanate). It was demonstrated that all the challenges involved in the construction and application of self-healing materials were overcome by the chemistry of NHCs substrates that formed reversible adducts with a variety of reagents, including other NHCs, organic electrophiles, and transition metals. The study also explored the feasibility of preparing structurally reversible polymers based on NHCs chemistry. Bis(NHC) was selected as a suitable monomer for the investigations, as its reactive carhene moieties were connected through an extended π-system and featured flexible branched alkyl N-subslituents to enhance solubility in organic sohents.
引用
收藏
页码:3591 / 3593
页数:3
相关论文
共 35 条
[1]   Mercapto-N-phenylformimidoyl-1-ethyl-3-( 2-morpholinoethyl)benzimidazolinium inner salt [J].
Akkurt, M ;
Karaca, S ;
Küçükbay, H ;
Yilmaz, Ü ;
Büyükgüngör, O .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2005, 61 :O2875-O2877
[2]   1-cyclohexylmethyl-3-methyl-2-[(phenyl-imino)(sulfido)methyl]benzimidazolium [J].
Akkurt, Mehmet ;
Karaca, Selvi ;
Kucukbay, Hasan ;
Sireci, Nihat ;
Buyukgungor, Orhan .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 :O809-U1467
[3]   When and how do diaminocarbenes dimerize? [J].
Alder, RW ;
Blake, ME ;
Chaker, L ;
Harvey, JN ;
Paolini, F ;
Schütz, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (44) :5896-5911
[4]   Catalytic double-bond metathesis without the transition metal [J].
Bell, SA ;
Meyer, TY ;
Geib, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (36) :10698-10705
[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]   Microcapsules containing suspensions of carbon nanotubes [J].
Caruso, Mary M. ;
Schelkopf, Stuart R. ;
Jackson, Aaron C. ;
Landry, Alexandra M. ;
Braun, Paul V. ;
Moore, Jeffrey S. .
JOURNAL OF MATERIALS CHEMISTRY, 2009, 19 (34) :6093-6096
[7]   A thermally re-mendable cross-linked polymeric material [J].
Chen, XX ;
Dam, MA ;
Ono, K ;
Mal, A ;
Shen, HB ;
Nutt, SR ;
Sheran, K ;
Wudl, F .
SCIENCE, 2002, 295 (5560) :1698-1702
[8]   Adapting N-Heterocyclic Carbene/Azide Coupling Chemistry for Polymer Synthesis: Enabling Access to Aromatic Polytriazenes [J].
Coady, Daniel J. ;
Khramov, Dimitri M. ;
Norris, Brent C. ;
Tennyson, Andrew G. ;
Bielawski, Christopher W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5187-5190
[9]   Reversible carboxylation of N-heterocyclic carbenes [J].
Duong, HA ;
Tekavec, TN ;
Arif, AM ;
Louie, J .
CHEMICAL COMMUNICATIONS, 2004, (01) :112-113
[10]   Synthesis and Study of 5,5′-Bibenzimidazolylidenes and Their Bimetallic Complexes [J].
Er, Joyce A. V. ;
Tennyson, Andrew G. ;
Kamplain, Justin W. ;
Lynch, Vincent M. ;
Bielawski, Christopher W. .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2009, (13) :1729-1738