Oligo(p-quinone methide)s bridged with thiophene rings. Novel oligomeric, quinonoid pi-systems with high electron affinity

被引:6
作者
Kurata, H [1 ]
Hisamitsu, A [1 ]
Oda, M [1 ]
机构
[1] OSAKA UNIV,GRAD SCH SCI,DEPT CHEM,TOYONAKA,OSAKA 560,JAPAN
关键词
D O I
10.1016/S0040-4039(97)10323-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel cross-conjugated oligomers composed of p-quinone methides and thiophenes, synthesized up to tetramer, possess substantially high electron affinity (CV). Alkali metal reduction of the dimer yields a stereoisomeric mixture of stable dianions, and protonation with trifluoroacetic acid generates the corresponding monocation and dication depending on acid strength. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:8875 / 8878
页数:4
相关论文
共 12 条
[1]   COMPOUNDS OF POTENTIAL PHARMACOLOGICAL INTEREST .2. SOME HETEROCYCLIC AND CARBOCYCLIC SYSTEMS RELATED TO 1-PHENYLINDANE [J].
ACHESON, RM ;
MACPHEE, KE ;
PHILPOTT, PG ;
BARLTROP, JA .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (MAR) :698-705
[2]  
ACHESON RM, 1979, J HETEROCYCLIC CHEM, P1147
[3]   PREPARATION AND PROPERTIES OF THIOPHEN ANALOGUES OF PORPHYRINS AND RELATED SYSTEMS .3. [J].
AHMED, M ;
METHCOHN, O .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (11) :2104-&
[5]  
GIERKE W, 1973, TETRAHEDRON LETT, P3681
[6]  
HUNIG S, 1956, LIEBIGS ANN CHEM, V599, P131
[7]   GENERATION, CHARACTERIZATION, AND REACTIONS OF FULVENE DIANIONS [J].
KAWASE, T ;
FUJINO, S ;
ODA, M .
CHEMISTRY LETTERS, 1990, (09) :1683-1686
[8]   SYNTHESIS AND PROPERTIES OF OLIGO-6-(2-THIENYL)PENTAFULVENES [J].
KAWASE, T ;
KURATA, H ;
MORIKAWA, T ;
ODA, M .
TETRAHEDRON LETTERS, 1993, 34 (21) :3449-3452
[9]   ALKALI-METAL REDUCTION OF OLIGO-6-(2-THIENYL)PENTAFULVENES - SYNTHESIS OF OLIGOTHIENYLENEMETHINES ATTACHED WITH CYCLOPENTADIENIDE GROUPS [J].
KURATA, H ;
KAWASE, T ;
ODA, M .
CHEMISTRY LETTERS, 1994, (12) :2219-2222
[10]   QUINONE METHIDES AND FUCHSONES .30. SUBSTITUTION EFFECT IN ELECTRONIC ABSORPTION-SPECTRA OF 2-SUBSTITUTED AND 2,6-SUBSTITUTED 4-BENZHYDRYLIDENE-2,5-CYCLOHEXADIEN-1-ONES [J].
MUSIL, L ;
KOUTEK, B ;
VELEK, J ;
SOUCEK, M .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1984, 49 (09) :1949-1964