Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation

doi:10.1021/jo501402n

	Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation
	Qiu, Li 1,3; Wang, Xiao1 ; Zhao, Na1,3 ; Xu, Shiliang 1,2; An, Zengjian1 ; Zhuang, Xuhui 1,3; Lan, Zhenggang 1; Wen, Lirong 2; Wan, Xiaobo 1
	2014-12-05
发表期刊	JOURNAL OF ORGANIC CHEMISTRY
卷号	79 期号:23 页码:11339-11348
摘要	A newly developed reductive ring closure methodology to heteroacenes bearing a dihydropyrrolo[3,2-b]pyrrole core was systematically studied for its scope and limitation. The methodology involves (i) the cyclization of an o-aminobenzoic acid ester derivative to give an eight-membered cyclic dilactam, and (ii) the conversion of the dilactams into the corresponding diimidoyl chloride, which undergoes (iii) reductive ring closure to install the dihydropyrrolo[3,2-b]pyrrole core. The first step of the methodology plays the key role due to its substrate limitation, which suffers from the competition of oligomerization and hydrolysis. All the dilactams could successfully convert to the corresponding diimidoyl chlorides, most of which succeeded to give the dihydropyrrolo[3,2-b]pyrrole core. The influence of the substituents and the elongation of conjugated length on the photophysical properties of the obtained heteroacenes were then investigated systematically using UV-vis spectroscopy and cyclic voltammetry. It was found that chlorination and fluorination had quite a different effect on the photophysical properties of the heteroacene, and the ring fusing pattern also had a drastic influence on the band gap of the heteroacene. The successful preparation of a series of heteroacenes bearing a dihydropyrrolo[3,2-b]pyrrole core would provide a wide variety of candidates for further fabrication of organic field-effect transistor devices.
文章类型	Article
WOS标题词	Science & Technology ; Physical Sciences
DOI	10.1021/jo501402n
关键词[WOS]	FIELD-EFFECT TRANSISTORS ; ORGANIC SEMICONDUCTORS ; OPTICAL-PROPERTIES ; HIGH-PERFORMANCE ; DERIVATIVES ; INDOLE ; BASE
收录类别	SCI ; IC
语种	英语
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
WOS记录号	WOS:000346038300005
引用统计
文献类型	期刊论文
条目标识符	http://ir.qibebt.ac.cn/handle/337004/6279
专题	生物基及仿生高分子材料团队（过去）
作者单位	1.Chinese Acad Sci, CAS Key Lab Biobased Mat, Qingdao Inst Bioenergy & Bioproc Technol, Qingdao 266101, Peoples R China 2.Qingdao Univ Sci & Technol, State Key Lab Base Ecochem Engn, Coll Chem & Mol Engn, Qingdao 266042, Peoples R China 3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
推荐引用方式 GB/T 7714	Qiu, Li,Wang, Xiao,Zhao, Na,et al. Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation[J]. JOURNAL OF ORGANIC CHEMISTRY,2014,79(23):11339-11348.
APA	Qiu, Li.,Wang, Xiao.,Zhao, Na.,Xu, Shiliang.,An, Zengjian.,...&Wan, Xiaobo.(2014).Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation.JOURNAL OF ORGANIC CHEMISTRY,79(23),11339-11348.
MLA	Qiu, Li,et al."Reductive Ring Closure Methodology toward Heteroacenes Bearing a Dihydropyrrolo[3,2-b]pyrrole Core: Scope and Limitation".JOURNAL OF ORGANIC CHEMISTRY 79.23(2014):11339-11348.