Facile Synthesis of 3-Alkoxy-4-cyanothiophenes As New Building Blocks for Donor-Acceptor Conjugated Systems

被引:52
作者
Hergue, Noemie [1 ]
Mallet, Charlotte [1 ]
Savitha, Gurunathan [1 ]
Allain, Magali [1 ]
Frere, Pierre [1 ]
Roncali, Jean [1 ]
机构
[1] LUNAM Univ, Grp Linear Conjugated Syst, MOLTECH Anjou UMR CNRS 6200, F-49045 Angers, France
关键词
BAND-GAP; ELECTRONIC-PROPERTIES; OXIDATION; POLYMERS; 3,4-DIARYL-2,5-DIHYDROTHIOPHENES; OLIGOMERS;
D O I
10.1021/ol200296j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Alkoxy-4-cyanothiophenes are efficiently synthesized in two steps from the readily available 4-cyano-3-oxotetrahydrothiophene. Regioisomers of bithiophene derivatives are easily synthesized by playing on the strong electronic dissymmetry of the thiophene ring induced by the alkoxy and cyano groups.
引用
收藏
页码:1762 / 1765
页数:4
相关论文
共 34 条
[1]   FRIES REARRANGEMENT OF SOME 3-ACETOXY-THIOPHENES AND 3-PROPIONYLOXY-THIOPHENES [J].
BANKS, MR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (03) :507-513
[2]  
BARALDI PG, 1985, SYNTHESIS-STUTTGART, P969
[3]   Effect of carbonitrile and hexyloxy substituents on alternated copolymer of polythiophene-Performances in photovoltaic cells [J].
Berson, Solenn ;
Cecioni, Samy ;
Billon, Martial ;
Kervella, Yann ;
de Bettignies, Remi ;
Bailly, Severine ;
Guillerez, Stephane .
SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2010, 94 (05) :699-708
[4]   Fine tuning of the electronic properties of linear π-conjugated oligomers by covalent bridging [J].
Blanchard, P ;
Verlhac, P ;
Michaux, L ;
Frère, P ;
Roncali, J .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (04) :1244-1255
[5]   Bridged dithienylethylenes as precursors of small bandgap electrogenerated conjugated polymers [J].
Blanchard, P ;
Brisset, H ;
Illien, B ;
Riou, A ;
Roncali, J .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2401-2408
[6]   RELATIONSHIP BETWEEN BAND-GAP AND BOND LENGTH ALTERNATION IN ORGANIC CONJUGATED POLYMERS [J].
BREDAS, JL .
JOURNAL OF CHEMICAL PHYSICS, 1985, 82 (08) :3808-3811
[7]   Development of Novel Conjugated Donor Polymers for High-Efficiency Bulk-Heterojunction Photovoltaic Devices [J].
Chen, Junwu ;
Cao, Yong .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (11) :1709-1718
[8]   Synthesis of Conjugated Polymers for Organic Solar Cell Applications [J].
Cheng, Yen-Ju ;
Yang, Sheng-Hsiung ;
Hsu, Chain-Shu .
CHEMICAL REVIEWS, 2009, 109 (11) :5868-5923
[9]   COMPETITION FOR REGIOCHEMICAL CONTROL BETWEEN SUBSTITUENTS OF SOME 2,3-DISUBSTITUTED BUTA-1,3-DIENES IN THE DIELS-ALDER REACTIONS [J].
CHOU, TS ;
CHANG, CY ;
WU, MC ;
HUNG, SH ;
LIU, HM ;
YEH, WY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (22) :1643-1644
[10]   Oxidation of 3,4-diaryl-2,5-dihydrothiophenes to 3,4-diarylthiophenes using CuBr2:: Simple and efficient preparation of 3,4-diarylthiophenes [J].
Dang, Yizhe ;
Chen, Yi .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (34) :5661-5664