An Excellent Fluorescent Dye with a Twistable Aromatic Chain and Its Axially Chiral Crystals

doi:10.1021/jp900514e

CORC > 化学研究所 > 中国科学院化学研究所

	An Excellent Fluorescent Dye with a Twistable Aromatic Chain and Its Axially Chiral Crystals
	Ma, Yan; Hao, Rui; Shao, Guangsheng; Wang, Yuan
刊名	JOURNAL OF PHYSICAL CHEMISTRY A
	2009-04-30
卷号	113 期号:17 页码:5066-5072
ISSN号	1089-5639
DOI	10.1021/jp900514e
英文摘要	A new organic fluorescent dye, 2,4-dichloro-6-[p-(N,N-diethylamino)biphenyly]-1,3,5-triazine (DBQ), with an electron withdrawing-donating pair bridged by a twistable aromatic chain has been synthesized. DBQ exhibits high fluorescence quantum yields (0.96 in hexane and 0.71 in THF), high extinction coefficients, and an excitation window extending up to similar to 480 nm. Due to the strong intramolecular charge transfer character., DBQ shows obviously solvent-dependent Stokes shifts with a value as high as 6360 cm(-1) in THF and controllable fluorescence emission in the visible region from "blue" to "orange". The axially chiral structures of DBQ crystals were clearly revealed by the X-ray analyses and CD spectroscopy measurements. Two enantiomers of DBQ were obtained by spontaneous resolution upon crystallization without any chiral auxiliary. The low rotation barriers around the interannular bonds in DBQ molecules resulted in an efficient and selective multiplication of each of the chiral structures when DBQ crystallized in THF at room temperature in the presence of an enantiopure crystal seed, leaving racemized DBQ molecules in the solution. The special crystalline properties of DBQ provided a new approach to the design and synthesis of organic chiral crystals. The photophysical properties of' DBQ make it promising in the preparation of new fluorescent probes with high sensitivity.
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000265529800033
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/67377]
专题	中国科学院化学研究所
通讯作者	Wang, Yuan
作者单位	Peking Univ, Beijing Natl Lab Mol Sci, State Key Lab Struct Chem Unstable & Stable Speci, Coll Chem & Mol Engn, Beijing 100871, Peoples R China
推荐引用方式 GB/T 7714	Ma, Yan,Hao, Rui,Shao, Guangsheng,et al. An Excellent Fluorescent Dye with a Twistable Aromatic Chain and Its Axially Chiral Crystals[J]. JOURNAL OF PHYSICAL CHEMISTRY A,2009,113(17):5066-5072.
APA	Ma, Yan,Hao, Rui,Shao, Guangsheng,&Wang, Yuan.(2009).An Excellent Fluorescent Dye with a Twistable Aromatic Chain and Its Axially Chiral Crystals.JOURNAL OF PHYSICAL CHEMISTRY A,113(17),5066-5072.
MLA	Ma, Yan,et al."An Excellent Fluorescent Dye with a Twistable Aromatic Chain and Its Axially Chiral Crystals".JOURNAL OF PHYSICAL CHEMISTRY A 113.17(2009):5066-5072.