Synthesis and characterization of radical oligothiophenes: A new class of thiophene-based conjugated homologues

被引:50
作者
Pappenfus, TM [1 ]
Mann, KR [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
关键词
D O I
10.1021/ol026292l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A series of thiophene-based homologues with an aromatic core surrounded by terthiophene "arms" with acetylene linkages has been synthesized by using Sonogashira coupling methods. The homologues were investigated spectroscopically in solution and in the solid state. They display extended pi-conjugation through the aromatic core that affects the strong emission and redox properties.
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收藏
页码:3043 / 3046
页数:4
相关论文
共 26 条
[11]   Hexakis(terthiophenylthio)benzene as a new class liquid crystalline molecule [J].
Inoue, S ;
Nishiguchi, S ;
Murakami, S ;
Aso, Y ;
Otsubo, T ;
Vill, V ;
Mori, A ;
Ujiie, S .
JOURNAL OF CHEMICAL RESEARCH-S, 1999, (10) :596-597A
[12]   Synthesis and characterization of the electronic and electrochemical properties of thienylenevinylene oligomers with multinanometer dimensions [J].
Jestin, I ;
Frère, P ;
Mercier, N ;
Levillain, E ;
Stievenard, D ;
Roncali, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8150-8158
[13]   THE 3RD-ORDER OPTICAL NONLINEARITY OF THE PHENYLETHYNYL-SUBSTITUTED BENZENE SYSTEM [J].
KONDO, K ;
YASUDA, S ;
SAKAGUCHI, T ;
MIYA, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (01) :55-56
[14]   Crystal engineering of conjugated oligomers and the spectral signature of π stacking in conjugated oligomers and polymers [J].
Koren, AB ;
Curtis, MD ;
Kampf, JW .
CHEMISTRY OF MATERIALS, 2000, 12 (06) :1519-+
[15]  
Kotha S, 1999, SYNLETT, P1621
[16]   SYNTHESIS OF HIGH-CARBON MATERIALS FROM ACETYLENIC PRECURSORS - PREPARATION OF AROMATIC MONOMERS BEARING MULTIPLE ETHYNYL GROUPS [J].
NEENAN, TX ;
WHITESIDES, GM .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2489-2496
[17]   A π-stacking terthiophene-based quinodimethane is an n-channel conductor in a thin film transistor [J].
Pappenfus, TM ;
Chesterfield, RJ ;
Frisbie, CD ;
Mann, KR ;
Casado, J ;
Raff, JD ;
Miller, LL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (16) :4184-4185
[18]  
Pearson DL, 1997, SYNTHETIC MET, V84, P303, DOI 10.1016/S0379-6779(97)80760-6
[19]   Rapid syntheses of oligo(2,5-thiophene ethynylene)s with thioester termini: Potential molecular scale wires with alligator clips [J].
Pearson, DL ;
Tour, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1376-1387
[20]   CONVENIENT SYNTHESIS OF ACETYLENES - CATALYTIC SUBSTITUTIONS OF ACETYLENIC HYDROGEN WITH BROMOALKENES, IODOARENES, AND BROMOPYRIDINES [J].
SONOGASHIRA, K ;
TOHDA, Y ;
HAGIHARA, N .
TETRAHEDRON LETTERS, 1975, (50) :4467-4470