ICCAS OpenIR
Synthesis, structures, and properties of disubstituted heteroacenes on one side containing both pyrrole and thiophene rings
Qi, Ting2; Qiu, Wenfeng1; Liu, Yunqi1; Zhang, Hengjun2; Gao, Xike2; Liu, Ying2; Lu, Kun2; Du, Chunyan2; Yu, Gui1; Zhu, Daoben1
2008-06-20
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume73Issue:12Pages:4638-4643
AbstractA 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.
DOI10.1021/jo800622y
Indexed BySCI ; IC
Language英语
WOS IDWOS:000256757100035
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:39[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/65202
Collection中国科学院化学研究所
Corresponding AuthorLiu, Yunqi
Affiliation1.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
Recommended Citation
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.
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