Synthesis, structures, and properties of disubstituted heteroacenes on one side containing both pyrrole and thiophene rings

doi:10.1021/jo800622y

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	Synthesis, structures, and properties of disubstituted heteroacenes on one side containing both pyrrole and thiophene rings
	Qi, Ting 2; Qiu, Wenfeng 1; Liu, Yunqi 1; Zhang, Hengjun 2; Gao, Xike 2; Liu, Ying 2; Lu, Kun 2; Du, Chunyan 2; Yu, Gui 1; Zhu, Daoben 1
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2008-06-20
卷号	73 期号:12 页码:4638-4643
ISSN号	0022-3263
DOI	10.1021/jo800622y
英文摘要	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.
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000256757100035
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/65201]
专题	中国科学院化学研究所
通讯作者	Liu, Yunqi
作者单位	1.Chinese Acad Sci, Inst Chem, Organ Solids Lab, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China 2.Chinese Acad Sci, Grad Sch, Beijing 100190, Peoples R China
推荐引用方式 GB/T 7714	Qi, Ting,Qiu, Wenfeng,Liu, Yunqi,et al. Synthesis, structures, and properties of disubstituted heteroacenes on one side containing both pyrrole and thiophene rings[J]. JOURNAL OF ORGANIC CHEMISTRY,2008,73(12):4638-4643.
APA	Qi, Ting.,Qiu, Wenfeng.,Liu, Yunqi.,Zhang, Hengjun.,Gao, Xike.,...&Zhu, Daoben.(2008).Synthesis, structures, and properties of disubstituted heteroacenes on one side containing both pyrrole and thiophene rings.JOURNAL OF ORGANIC CHEMISTRY,73(12),4638-4643.
MLA	Qi, Ting,et al."Synthesis, structures, and properties of disubstituted heteroacenes on one side containing both pyrrole and thiophene rings".JOURNAL OF ORGANIC CHEMISTRY 73.12(2008):4638-4643.