Synthesis and Electronic, Optical, and Electrochemical Properties of a Series of Tetracyanobutadiene-Substituted Carbazoles
Synthesis and Electronic, Optical, and Electrochemical Properties of a Series of Tetracyanobutadiene-Substituted Carbazoles
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DOI：
10.1002/ajoc.201500431
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发表时间：
2016-02-01
影响因子：
2.7
通讯作者：
Nakamura, Yosuke
中科院分区：
文献类型：
--
作者：
Kato, Shin-ichiro;Noguchi, Hiroto;Nakamura, Yosuke
通过四氰基乙烯（TCNE）与含炔基的咔唑衍生物的[2+2]环加成反应，再经逆电环化反应，合成了一系列四氰基丁二烯（TCBD）取代的咔唑生色团。咔唑的反应性取决于咔唑和炔属部分之间的共轭连接性、咔唑部分的数目和炔属部分的长度。所有的产品功能在可见光区的分子内电荷转移带。TCBD取代在1-位的咔唑产生小HOMO-LUMO间隙相比，在2-和3-位。评价了咔唑部分的TCBD取代模式与给体-受体-缀合的有效性之间的关系，并且确定了-缀合按位置1的顺序是有效的
A series of tetracyanobutadiene (TCBD)-substituted carbazole chromophores were synthesized by formal [2+2] cycloaddition between tetracyanoethylene (TCNE) and carbazole derivatives containing an acetylenic moiety, followed by retro-electrocyclization. The reactivity of the carbazole varied depending on the conjugation connectivity between the carbazole and acetylenic moieties, the number of the carbazole moieties, and the length of the acetylenic moieties. All of the products feature intramolecular charge-transfer bands in the visible region. TCBD substitution at the 1-position of the carbazole gave rise to small HOMO-LUMO gaps compared to that at the 2- and 3-positions. The relationship between the TCBD substitution pattern of the carbazole moiety and the effectiveness of donor-acceptor -conjugation was evaluated, and it was established that the -conjugation was effective in order of positions 1