Pyrazine-containing acene-type molecular ribbons with up to 16 rectilinearly arranged fused aromatic rings

doi:10.1021/ja800311a

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	Pyrazine-containing acene-type molecular ribbons with up to 16 rectilinearly arranged fused aromatic rings
	Gao, Baoxiang 1,2; Wang, Ming 1; Cheng, Yanxiang 1; Wang, Lixiang 1; Jing, Xiabin 1; Wang, Fosong 1
刊名	JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
	2008-07-02
卷号	130 期号:26 页码:8297-8306
ISSN号	0002-7863
DOI	10.1021/ja800311a
英文摘要	A series of acene-type conjugated molecules(1-5) containing 2-6 pyrazine units and up to 16 rectilinearly arranged fused aromatic rings were synthesized by condensation coupling of 1,2-diamines and 1,2-diketones. The energy gap of the molecules estimated from absorption edge decreases with an increase in molecular length, indicating the well-delocalized nature of the molecules. The cyclic voltarnmetry measurements suggest that the n-type properties of these ribbonlike pyrazine derivatives are dependent on the molecular length and the number of the pyrazine units. As the number of pyrazine units and the molecular length increase, the first reduction wave onset is shifted from -1.16 to -0.62 V (vs Ag/AgCl), corresponding to the LUMO energy levels of -3.24 and -3.78 eV, respectively. These molecules tend to aggregate in solution more readily with an increase in molecular length, as evident by H-1 NMR and LIV-vis absorption spectra. Introduction of t-butyl groups in pyrene units can noticeably suppress the aggregation of these molecules in solution. High electron affinity, high environmental stability, and ease of structural modification make these compounds excellent candidates as a new class of n-type semiconductors.
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000257152800045
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/64325]
专题	中国科学院化学研究所
通讯作者	Wang, Lixiang
作者单位	1.Chinese Acad Sci, Changchun Inst Appl Chem, State Key Lab Polymer Phys & Chem, Changchun 130022, Peoples R China 2.Hebei Univ, Coll Chem & Environm Sci, Baoding 071002, Peoples R China
推荐引用方式 GB/T 7714	Gao, Baoxiang,Wang, Ming,Cheng, Yanxiang,et al. Pyrazine-containing acene-type molecular ribbons with up to 16 rectilinearly arranged fused aromatic rings[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2008,130(26):8297-8306.
APA	Gao, Baoxiang,Wang, Ming,Cheng, Yanxiang,Wang, Lixiang,Jing, Xiabin,&Wang, Fosong.(2008).Pyrazine-containing acene-type molecular ribbons with up to 16 rectilinearly arranged fused aromatic rings.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,130(26),8297-8306.
MLA	Gao, Baoxiang,et al."Pyrazine-containing acene-type molecular ribbons with up to 16 rectilinearly arranged fused aromatic rings".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 130.26(2008):8297-8306.