Fused Bispentacenequinone and Its Unexpected Michael Addition

被引:46
作者
Zhang, Xiaojie [1 ]
Li, Jinling [1 ]
Qu, Hemi [1 ]
Chi, Chunyan [1 ]
Wu, Jishan [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
关键词
FUNCTIONALIZED PENTACENE; ORGANIC ELECTRONICS; RED EMITTERS; DERIVATIVES; TRANSISTORS; HEPTACENE; ACENES; DYES;
D O I
10.1021/ol101720e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Fused bispentacenequinone 2 was synthesized by photocyclization of bispentacenequinone 1. Unusual regioselective Michael addition was observed for 2 when excess aryl Grignard reagent was used. Subsequent acidification and oxidation in air gave diaryl-substituted bispentacenequinone 3. Tetra-aryl-substituted fused bispentacenequinone 4 was obtained from 3 after the second Michael addition followed by oxidation in air.
引用
收藏
页码:3946 / 3949
页数:4
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