A Luminescent Nitrogen-Containing Polycyclic Aromatic Hydrocarbon Synthesized by Photocyclodehydrogenation with Unprecedented Regioselectivity

	A Luminescent Nitrogen-Containing Polycyclic Aromatic Hydrocarbon Synthesized by Photocyclodehydrogenation with Unprecedented Regioselectivity
	Gu, Xinggui 1,2,3,4; Wang, Hong 1,2,3,4; Roose, Jesse 1,2,3,4; He, Zikai 1,2,3,4; Zhou, Yue 5; Yan, Yongli 5; Cai, Yuanjing 1,2,3,4; Shi, Heping 2,3,4; Zhang, Yilin 2,3,4; Sung, Herman H. Y.2,3,4
刊名	CHEMISTRY-A EUROPEAN JOURNAL
	2015-12-01
卷号	21 期号:49 页码:17973-17980
关键词	aggregation luminescence optical waveguides polycycles regioselectivity
英文摘要	We present a nitrogen-containing polycyclic aromatic hydrocarbon (N-PAH), namely 12-methoxy-9-(4-methoxyphenyl)-5,8-diphenyl-4-(pyridin-4-yl) pyreno[1,10,9-h,i,j]-isoquinoline (c-TPE-ON), which exhibits high quantum-yield emission both in solution (blue) and in the solid state (yellow). This molecule was unexpectedly obtained by a three-fold, highly regioselective photocyclodehydrogenation of a tetraphenylethylene-derived AIEgen. Based on manifold approaches involving UV/Vis, photoluminescence, and NMR spectroscopy as well as HRMS, we propose a reasonable mechanism for the formation of the disk-like N-PAH that is supported by density functional theory calculations. In contrast to most PAHs that are commonly used, our system does not suffer from entire fluorescence quenching in the solid state due to the peripheral aromatic rings preventing p-p stacking interactions, as evidenced by single-crystal X-ray analysis. Moreover, its rod-like microcrystals exhibit excellent optical waveguide properties. Hence, c-TPE-ON comprises a N-PAH with unprecedented luminescent properties and as such is a promising candidate for fabricating organic optoelectronic devices. Our design and synthetic strategy might lead to a more general approach to the preparation of solution-and solid-state luminescent PAHs.
收录类别	SCI
语种	英语
公开日期	2016-05-09
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/29539]
专题	化学研究所_光化学实验室
作者单位	1.HKUST Shenzhen Res Inst, Shenzhen 518057, Peoples R China 2.Hong Kong Univ Sci & Technol, Dept Chem, Phys, Kowloon, Hong Kong, Peoples R China 3.Hong Kong Univ Sci & Technol, Inst Mol Funct Mat, Div Life Sci, Kowloon, Hong Kong, Peoples R China 4.Hong Kong Univ Sci & Technol, Div Biomed Engn, Kowloon, Hong Kong, Peoples R China 5.Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci BNLMS, Beijing 100190, Peoples R China 6.Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China 7.S China Univ Technol, State Key Lab Luminescent Mat & Devices, SCUT HKUST Joint Res Lab, Guangdong Innovat Res Team, Guangzhou 51640, Guangdong, Peoples R China
推荐引用方式 GB/T 7714	Gu, Xinggui,Wang, Hong,Roose, Jesse,et al. A Luminescent Nitrogen-Containing Polycyclic Aromatic Hydrocarbon Synthesized by Photocyclodehydrogenation with Unprecedented Regioselectivity[J]. CHEMISTRY-A EUROPEAN JOURNAL,2015,21(49):17973-17980.
APA	Gu, Xinggui.,Wang, Hong.,Roose, Jesse.,He, Zikai.,Zhou, Yue.,...&Tang, Ben Zhong.(2015).A Luminescent Nitrogen-Containing Polycyclic Aromatic Hydrocarbon Synthesized by Photocyclodehydrogenation with Unprecedented Regioselectivity.CHEMISTRY-A EUROPEAN JOURNAL,21(49),17973-17980.
MLA	Gu, Xinggui,et al."A Luminescent Nitrogen-Containing Polycyclic Aromatic Hydrocarbon Synthesized by Photocyclodehydrogenation with Unprecedented Regioselectivity".CHEMISTRY-A EUROPEAN JOURNAL 21.49(2015):17973-17980.