Synthesis, structure, fullerene-binding and resolution of C-3-symmetric cavitands with rigid and deep cavities

doi:10.1039/c1ob06465g

CORC > 化学研究所 > 中国科学院化学研究所

	Synthesis, structure, fullerene-binding and resolution of C-3-symmetric cavitands with rigid and deep cavities
	Yu, Jin-Tao; Huang, Zhi-Tang; Zheng, Qi-Yu
刊名	ORGANIC & BIOMOLECULAR CHEMISTRY
	2012
卷号	10 期号:7 页码:1359-1364
ISSN号	1477-0520
DOI	10.1039/c1ob06465g
英文摘要	An efficient palladium-catalyzed Suzuki-Miyaura coupling method involving the reaction between CTV-Br-3 and a variety of aryl and heteroaryl boronic acids in the presence of indolyl phosphane ligands has been developed. This reaction procedure provided a series of C-3-symmetric aryl-extended rigid cavitands for the first time. X-ray crystal structure analysis revealed that the phenyl substituted cavitand 5a has much larger rim edges and cavity height. This macrocyclic host adopts a linear head-to-tail "hand-shake" self-inclusion arrangement in the crystalline state. The fluorescence of 5a was considerably quenched upon the addition of C-60, with a binding constant of 78 700 +/- 2300 dm(3) mol(-1) and a 1:1 stoichiometry according to the Job's plot. The interaction of C-60 with 5a in the excited state is stronger than that with CTV, which could be attributed to more binding sites in the extended arms of 5a. Moreover, optically active C-3-symmetric cavitands (+)- and (-)-6 were easily obtained with high efficiency through chemical resolution.
语种	英语
出版者	ROYAL SOC CHEMISTRY
WOS记录号	WOS:000299476800006
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/47677]
专题	中国科学院化学研究所
通讯作者	Zheng, Qi-Yu
作者单位	Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
推荐引用方式 GB/T 7714	Yu, Jin-Tao,Huang, Zhi-Tang,Zheng, Qi-Yu. Synthesis, structure, fullerene-binding and resolution of C-3-symmetric cavitands with rigid and deep cavities[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2012,10(7):1359-1364.
APA	Yu, Jin-Tao,Huang, Zhi-Tang,&Zheng, Qi-Yu.(2012).Synthesis, structure, fullerene-binding and resolution of C-3-symmetric cavitands with rigid and deep cavities.ORGANIC & BIOMOLECULAR CHEMISTRY,10(7),1359-1364.
MLA	Yu, Jin-Tao,et al."Synthesis, structure, fullerene-binding and resolution of C-3-symmetric cavitands with rigid and deep cavities".ORGANIC & BIOMOLECULAR CHEMISTRY 10.7(2012):1359-1364.