High-Yielding Alkyne-Tetracyanoethylene Addition Reactions: A Powerful Tool for Analyzing Alkyne-Linked Conjugated Polymer Structures

被引：26

作者：

Fujita, Hiroyuki ^{[3
]}

Tsuboi, Kazuma ^{[3
]}

Michinobu, Tsuyoshi ^{[1
,2
]}

机构：

[1] Tokyo Inst Technol, Global Edge Inst, Meguro Ku, Tokyo 1528550, Japan

[2] Japan Sci & Technol Agcy JST, PRESTO, Tokyo, Japan

[3] Tokyo Inst Technol, Dept Organ & Polymer Mat, Meguro Ku, Tokyo 1528552, Japan

来源：

MACROMOLECULAR CHEMISTRY AND PHYSICS | 2011年 / 212卷 / 16期

关键词：

conjugated polymers; electrochemistry; functionalization of polymers; CHARGE-TRANSFER INTERACTIONS; DONOR-ACCEPTOR CHROMOPHORES; ONE-STEP SYNTHESIS; CLICK SYNTHESIS; POLY(ARYLENEETHYNYLENE)S; POSTFUNCTIONALIZATION; NONLINEARITIES; DERIVATIVES; TCNQ;

D O I：

10.1002/macp.201100198

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Poly(o-phenyleneethynylene) and poly(o-phenylenebutadiynylene) derivatives are synthesized by the Sonogashira polycondensation or oxidative polymerization of an asymmetric monomer, 3,4-diethynyl-N, N-dihexylaniline. Postfunctionalization of the poly(o-phenyleneethylene) derivatives is unsuccessful due to the occurrence of undesired side reactions. In contrast, the poly(o-phenylenebutadiynylene) derivative is converted into the donor-acceptor type polymer without side reactions. The resulting polymer features a well-defined charge-transfer (CT) band in the Vis-NIR region and redox activity in both the anodic and cathodic directions. The results suggest that the oxidative polymerization mainly proceeds through the pseudo two-step pathway.

引用

页码：1758 / 1766

页数：9

共 32 条

[1] Donor-substituted octacyano[4]dendralenes: a new class of cyano-rich non-planar organic acceptors [J].

Breiten, Benjamin ;

Wu, Yi-Lin ;

Jarowski, Peter D. ;

Gisselbrecht, Jean-Paul ;

Boudon, Corinne ;

Griesser, Markus ;

Onitsch, Christine ;

Gescheidt, Georg ;

Schweizer, W. Bernd ;

Langer, Nicolle ;

Lennartz, Christian ;

Diederich, Francois .

CHEMICAL SCIENCE, 2011, 2 (01) :88-93

[2] Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications [J].

Bunz, UHF .

CHEMICAL REVIEWS, 2000, 100 (04) :1605-1644

[3] Poly(aryleneethynylene)s [J].

Bunz, Uwe H. F. .

MACROMOLECULAR RAPID COMMUNICATIONS, 2009, 30 (9-10) :772-805

[4] The Glaser reaction mechanism. A DFT study [J].

Fomina, L ;

Vazquez, B ;

Tkatchouk, E ;

Fomine, S .

TETRAHEDRON, 2002, 58 (33) :6741-6747

[5] Non-planar push-pull chromophores [J].

Kato, Shin-ichiro ;

Diederich, Francois .

CHEMICAL COMMUNICATIONS, 2010, 46 (12) :1994-2006

[6] One-electron-reduced and -oxidized stages of donor-substituted 1,1,4,4-tetracyanobuta-1,3-dienes of different molecular architectures [J].

Kivala, Milan ;

Stanoeva, Tsvetanka ;

Michinobu, Tsuyoshi ;

Frank, Brian ;

Gescheidt, Georg ;

Diederich, Francois .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (25) :7638-7647

[7] A novel reaction of 7,7,8,8-tetracyanoquinodimethane (TCNQ): charge-transfer chromophores by [2+2] cycloaddition with alkynes [J].

Kivala, Milan ;

Boudon, Corinne ;

Gisselbrecht, Jean-Paul ;

Seiler, Paul ;

Gross, Maurice ;

Diederich, Francois .

CHEMICAL COMMUNICATIONS, 2007, (45) :4731-4733

[8] Organic Super-Acceptors with Efficient Intramolecular Charge-Transfer Interactions by [2+2] Cycloadditions of TCNE, TCNQ, and F4-TCNQ to Donor-Substituted Cyanoalkynes [J].

Kivala, Milan ;

Boudon, Corinne ;

Gisselbrecht, Jean-Paul ;

Enko, Barbara ;

Seiler, Paul ;

Mueller, Imke B. ;

Langer, Nicolle ;

Jarowski, Peter D. ;

Gescheidt, Georg ;

Diederich, Francois .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (16) :4111-4123

[9] Acetylene-Derived Strong Organic Acceptors for Planar and Nonplanar Push-Pull Chromophores [J].

Kivala, Milan ;

Diederich, Francois .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (02) :235-248

[10]

Leclerc M., 2010, Design and Synthesis of Conjugated Polymers

← 1 2 3 4 →