Synthesis, structures, and properties of disubstituted heteroacenes on one side containing both pyrrole and thiophene rings.
Synthesis, structures, and properties of disubstituted heteroacenes on one side containing both pyrrole and thiophene rings.
复制标题
DOI：
10.1021/jo800622y
复制
发表时间：
2008-05
期刊：
影响因子：
--
通讯作者：
Ting Qi;Wenfeng Qiu;Yunqi Liu;Hengjun Zhang;Xike Gao;Ying Liu;Kun Lu;C. Du;G. Yu;Daoben Z
中科院分区：
文献类型：
--
作者：
Ting Qi;Wenfeng Qiu;Yunqi Liu;Hengjun Zhang;Xike Gao;Ying Liu;Kun Lu;C. Du;G. Yu;Daoben Z
以3，3 '-二溴-2，2'-联吲哚为原料，通过与二苯磺酰基硫醚和有机锂的分子内环化反应，合成了一系列新的含吡咯和呋喃环的梯型杂并苯化合物5，6-二取代二吲哚并[3，2-B：4，5-b ']噻吩（DIT）.单晶X-射线衍射结果表明，5，6-二丙基二吲哚并[3，2-B：4，5-b ']噻吩（4 B）形成人字形堆积基序，5，6-二（对甲苯基）二吲哚并[3，2-B：4，5-b']噻吩（4 d）形成平行堆积基序。它们都具有S-S接触，增强了分子之间的电子传输。它们的物理化学性质表明，二吲哚并[3，2- B：4，5-b ']噻吩的骨架比吲哚并[3，2-B]咔唑的骨架更有利于在固体中聚集.大的带隙和低的HOMO能级可以导致更好的稳定性。
A new series of ladder-type heteroacenes containing both pyrrole and furan rings, 5,6-disubstituted diindolo[3,2-b:4,5-b']thiophenes (DITs), were effectively synthesized from N-functionalized 3,3'-dibromo-2,2'-biindoles undergoing intramolecular cyclization with bis(phenylsulfonyl) sulfide and organolithium. Single-crystal X-ray results demonstrate that 5,6-dipropyldiindolo[3,2-b:4,5-b']thiophene (4b) forms a herringbone-type of packing motif and 5,6-di(p-tolyl)diindolo[3,2-b:4,5-b']thiophene (4d) forms a parallel packing motif. Both of them have S-S contacts, enhancing the electronic transport between molecules. Their photophysical properties suggest that the skeleton of diindolo[3,2- b:4,5-b']thiophene is more favorable to aggregate in solid than that of indolo[3,2-b]carbazole. The large band gaps and low-lying HOMO energy levels could result in much better stability.