Synthesis of [all]-S,S-dioxide oligothiophenes using HOF•CH3CN

被引:69
作者
Amir, E [1 ]
Rozen, S [1 ]
机构
[1] Tel Aviv Univ, Raymond & Beverly Sackler Fac Exact Sci, Sch Chem, IL-69978 Tel Aviv, Israel
关键词
fluorine; hypofluorous acid; oligomers; oxygenation; thiophenes;
D O I
10.1002/anie.200501681
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Nonaromatic stable polyenes are obtained by dioxygenation of oligothiophenes using HOF·CH3CN prepared in situ by passing F2 through aqueous acetonitrile (see scheme). These fully S,S-dioxygenated derivatives have a considerably smaller HOMO-LUMO gap than the parent compounds; furthermore, in the solid state they tend to form favorable π-π stacking interactions, unlike most non-oxidized oligothiophenes which adopt the herringbone" motif. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA."
引用
收藏
页码:7374 / 7378
页数:5
相关论文
共 38 条
[1]   2,2'-BITHIENYL DERIVATIVES - EPR INVESTIGATION OF THEIR RADICAL IONS IN SOLUTION, ELECTROCHEMICAL PROPERTIES, AND CRYSTAL-STRUCTURE [J].
ALEMAN, C ;
BRILLAS, E ;
DAVIES, AG ;
FAJARI, L ;
GIRO, D ;
JULIA, L ;
PEREZ, JJ ;
RIUS, J .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :3091-3099
[2]   High performance n-type organic field-effect transistors based on π-electronic systems with trifluoromethylphenyl groups [J].
Ando, S ;
Nishida, JI ;
Tada, H ;
Inoue, Y ;
Tokito, S ;
Yamashita, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (15) :5336-5337
[3]   Molecular packing and photoluminescence efficiency in odd-membered oligothiophene S,S-dioxides [J].
Antolini, L ;
Tedesco, E ;
Barbarella, G ;
Favaretto, L ;
Sotgiu, G ;
Zambianchi, M ;
Casarini, D ;
Gigli, G ;
Cingolani, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (37) :9006-9013
[4]   Oligothiophene S,S-dioxides: towards n-type semiconductor oligothiophenes? [J].
Arbizzani, C ;
Barbarella, G ;
Bongini, A ;
Favaretto, L ;
Mastragostino, M ;
Ostoja, P ;
Pudova, O ;
Zambianchi, M .
OPTICAL MATERIALS, 1998, 9 (1-4) :43-45
[5]  
Barbarella G, 1998, ADV MATER, V10, P551, DOI 10.1002/(SICI)1521-4095(199805)10:7<551::AID-ADMA551>3.0.CO
[6]  
2-Y
[7]   Oligothiophene-S,S-dioxides:: a new class of thiophene-based materials [J].
Barbarella, G ;
Pudova, O ;
Arbizzani, C ;
Mastragostino, M ;
Bongini, A .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1742-1745
[8]   Oligothiophene S,S-dioxides.: Synthesis and electronic properties in relation to the parent oligothiophenes [J].
Barbarella, G ;
Favaretto, L ;
Sotgiu, G ;
Zambianchi, M ;
Antolini, L ;
Pudova, O ;
Bongini, A .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5497-5506
[9]   SELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED OLIGOTHIOPHENES [J].
BAUERLE, P ;
WURTHNER, F ;
GOTZ, G ;
EFFENBERGER, F .
SYNTHESIS-STUTTGART, 1993, (11) :1099-1103
[10]   Synthesis of 1,10-N,N'-phenanthroline dioxides using HOF•CH3CN complex [J].
Carmeli, M ;
Rozen, S .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2131-2134