Unexpected Side Chain Oxidation in a Swivel Cruciform Oligothiophene

被引:10
作者
Koenen, Jan-Moritz [1 ]
Bilge, Askin [1 ]
Allard, Sybille [1 ]
Alle, Ronald [2 ]
Meerholz, Klaus [2 ]
Scherf, Ullrich [1 ]
机构
[1] Berg Univ Wuppertal, Makromol Chem & Inst Polymertechnol, D-42097 Wuppertal, Germany
[2] Univ Cologne, Inst Phys Chem, D-50939 Cologne, Germany
关键词
TRANSISTORS;
D O I
10.1021/ol900675f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two swivel cruciform oligothiophenes are investigated for the occurrence of oxidative ring closure reactions. Surprisingly, instead of intramolecular cyclizations, a regioselective side chain oxidation of two of the four alpha-methylene groups next to the terminal thiophene rings is detected for one of the oligomers. Such side chain oxidations may be one unintended degradation pathway in oligothiophene-based organic semiconductors used as the active layer of organic field effect transistors (OFETs), organic light emitting diodes (OLEDs), and organic solar cells (OSCs).
引用
收藏
页码:2149 / 2152
页数:4
相关论文
共 18 条
[1]  
Allard S., 2008, Angew. Chem, V120, P4138
[2]   Functionalized acenes and heteroacenes for organic electronics [J].
Anthony, John E. .
CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048
[3]  
BILGE A, 2006, THESIS BU WUPPERTAL
[4]   Swivel-cruciform oligothiophene dimers [J].
Bilge, Askin ;
Zen, Achmad ;
Forster, Michael ;
Li, Hongbo ;
Galbrecht, Frank ;
Nehls, Benjamin S. ;
Farrell, Tony ;
Neher, Dieter ;
Scherf, Ullrich .
JOURNAL OF MATERIALS CHEMISTRY, 2006, 16 (31) :3177-3182
[5]  
Brooks P, 1999, SYNTHESIS-STUTTGART, P1303
[6]   Partial fluorination overcomes herringbone crystal packing in small polycyclic aromatics [J].
Cho, DM ;
Parkin, SR ;
Watson, MD .
ORGANIC LETTERS, 2005, 7 (06) :1067-1068
[7]   Influence of alkyl substituents on the solution- and surface-organization of hexa-peri-hexabenzocoronenes [J].
Kastler, M ;
Pisula, W ;
Wasserfallen, D ;
Pakula, T ;
Müllen, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) :4286-4296
[8]   Synthesis of 2,5,8,11,14,17-hexafluoro-hexa-perihexabenzocoronene for n-type organic field-effect transistors [J].
Kikuzawa, Yoshihiro ;
Mori, Tomohiko ;
Takeuchi, Hisato .
ORGANIC LETTERS, 2007, 9 (23) :4817-4820
[9]   Planarized star-shaped oligothiophenes with enhanced π-electron delocalization [J].
Nicolas, Y ;
Blanchard, P ;
Levillain, E ;
Allain, M ;
Mercier, N ;
Roncali, J .
ORGANIC LETTERS, 2004, 6 (02) :273-276
[10]   4 NOVEL PHENYLDITHIENOINDOLE ISOMERS FROM THE OXIDATIVE PHOTOCYCLIZATION OF DITHIENYLPYRROLES [J].
PERRINE, DM ;
KAGAN, J ;
HUANG, DB ;
ZENG, K ;
TEO, BK .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) :2213-2216