Branched charge-transfer chromophores featuring a 4,5-dicyanoimidazole unit

被引:22
作者
Bures, Filip [1 ]
Kulhanek, Jiri [1 ]
Mikysek, Tomas [2 ]
Ludvik, Jiri [3 ]
Lokaj, Jan [4 ,5 ]
机构
[1] Univ Pardubice, Inst Organ Chem & Technol, Fac Chem Technol, Pardubice 53210, Czech Republic
[2] Univ Pardubice, Dept Analyt Chem, Fac Chem Technol, Pardubice 53210, Czech Republic
[3] Acad Sci Czech Republ, J Heyrovsky Inst Phys Chem, CR-18223 Prague 8, Czech Republic
[4] Slovak Univ Technol Bratislava, Fac Food & Chem Technol, Bratislava 81237, Slovakia
[5] Slovak Univ Technol, Fac Mat Sci & Technol, Trnava 91724, Slovakia
关键词
NONLINEAR-OPTICAL PROPERTIES; 2-PHOTON ABSORPTION; IMIDAZOLE; DONOR; CONJUGATION; MOLECULES; OLIGOTHIOPHENES; BENZIMIDAZOLE; DERIVATIVES; THIAZOLE;
D O I
10.1016/j.tetlet.2010.02.067
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Six branched and stable push-pull chromophores featuring 4,5-dicyanoimidazole as an acceptor moiety, an N,N-dimethylamino group as a donor and various pi-conjugated linkers are reported. Systematic extension of the pi-linker revealed that the optical and electrochemical properties of A-pi-D chromophores are mainly affected by the nature of the pi-conjugated backbone (length and planarity) as well as by the number of appended donors. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2055 / 2058
页数:4
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共 50 条
[1]   Novel heteroaromatic-based multi-branched dyes with enhanced two-photon absorption activity [J].
Abbotto, A ;
Beverina, L ;
Bozio, R ;
Facchetti, A ;
Ferrante, C ;
Pagani, GA ;
Pedron, D ;
Signorini, R .
CHEMICAL COMMUNICATIONS, 2003, (17) :2144-2145
[2]   Second-Order Nonlinear Optical Activity of Dipolar Chromophores Based on Pyrrole-Hydrazono Donor Moieties [J].
Abbotto, Alessandro ;
Beverina, Luca ;
Manfredi, Norberto ;
Pagani, Giorgio A. ;
Archetti, Graziano ;
Kuball, Hans-Georg ;
Wittenburg, Christian ;
Heck, Juergen ;
Holtmann, Jan .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (25) :6175-6185
[3]   ELECTRON-DONORS AND CYANOIMIDAZOLE ACCEPTORS - CYCLIC VOLTAMMETRY AND MOLECULAR ORBITAL STUDY [J].
ALLAN, DS ;
BERGSTROM, DF ;
RASMUSSEN, PG .
SYNTHETIC METALS, 1988, 25 (02) :139-155
[4]   Organic semiconductors for solution-processable field-effect transistors (OFETs) [J].
Allard, Sybille ;
Forster, Michael ;
Souharce, Benjamin ;
Thiem, Heiko ;
Scherf, Ullrich .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4070-4098
[5]   SYNTHESIS AND PROPERTIES OF NEW DERIVATIVES OF 4,5-DICYANOIMIDAZOLE AND 4,4',5,5'-TETRACYANO-2,2'-BIIMIDAZOLE [J].
APEN, PG ;
RASMUSSEN, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6178-6187
[6]   METALATION AND REACTION OF 4,5-DICYANOIMIDAZOLES WITH ALKYLLITHIUM REAGENTS [J].
APEN, PG ;
RASMUSSEN, PG .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (05) :1091-1095
[7]  
APEN PG, 1989, HETEROCYCLES, V29, P1325
[8]   Synthesis and characterization of novel (oligo)thienyl-imidazo-phenanthrolines as versatile π-conjugated systems for several optical applications [J].
Batista, Rosa M. F. ;
Costa, Susana P. G. ;
Belsley, M. ;
Lodeiro, Carlos ;
Raposo, M. Manuela M. .
TETRAHEDRON, 2008, 64 (39) :9230-9238
[9]   Synthesis and second-order nonlinear optical properties of new chromophores containing benzimidazole, thiophene, and pyrrole heterocycles [J].
Batista, Rosa M. F. ;
Costa, Susana P. G. ;
Belsley, M. ;
Raposo, M. Manuela M. .
TETRAHEDRON, 2007, 63 (39) :9842-9849
[10]   Synthesis and optical properties of novel, thermally stable phenanthrolines bearing an arylthienyl-imidazo conjugation pathway [J].
Batista, Rosa M. F. ;
Costa, Susana P. G. ;
Belsley, M. ;
Raposo, M. Manuela M. .
DYES AND PIGMENTS, 2009, 80 (03) :329-336