Synthesis, Structure, and Fullerene-Complexing Property of Azacalix[6]aromatics

doi:10.1021/jo5003714

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	Synthesis, Structure, and Fullerene-Complexing Property of Azacalix[6]aromatics
	Fa, Shi-Xin 1; Wang, Li-Xia 1; Wang, De-Xian 1; Zhao, Liang 2; Wang, Mei-Xiang 2
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2014-04-18
卷号	79 期号:8 页码:3559-3571
ISSN号	0022-3263
DOI	10.1021/jo5003714
英文摘要	Synthesis, structure, and fullerene-binding property of azacalix[6]aromatics were systematically studied. By means of [3 + 3] and [2 + 2 + 2] fragment coupling protocols, a number of azacalix[6]aromatics containing different combinations of benzene, pyridine, and pyrimidine rings and various substituents on the bridging nitrogen atoms were synthesized conveniently in moderate to good yields. The resulting macrocycles adopt in the solid state symmetric and heavily distorted 1,3,5-alternate conformations depending on the aromatic building units, whereas, in solution, they exist as a mixture of conformers that undergo rapid interchanges relative to the NMR time scale. All macrocycles were able to form 1:1 complexes with C-60 and C-70 in toluene with the association constants up to 7.28 x 10(4) M-1. In the crystalline state, azacalix[6]aromatics form complexes with C-60 and C-70 with 2:1, 1:1, and 1:2 stoichiometric ratios between host and guest. Azacalix[6]aromatics interact with fullerene by forming mainly the sandwich structure in which C-60 or C-70 is sandwiched by two macrocycles. X-ray molecular structures revealed that multiple pi-pi and CH-pi interactions between concave azacalix[6]aromatics and convex fullerenes C-60 and C-70 contribute a joint driving force to the formation of host-guest complexes.
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000334823800025
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/50167]
专题	中国科学院化学研究所
通讯作者	Wang, Mei-Xiang
作者单位	1.Chinese Acad Sci, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Inst Chem, Beijing 100190, Peoples R China 2.Tsinghua Univ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China
推荐引用方式 GB/T 7714	Fa, Shi-Xin,Wang, Li-Xia,Wang, De-Xian,et al. Synthesis, Structure, and Fullerene-Complexing Property of Azacalix[6]aromatics[J]. JOURNAL OF ORGANIC CHEMISTRY,2014,79(8):3559-3571.
APA	Fa, Shi-Xin,Wang, Li-Xia,Wang, De-Xian,Zhao, Liang,&Wang, Mei-Xiang.(2014).Synthesis, Structure, and Fullerene-Complexing Property of Azacalix[6]aromatics.JOURNAL OF ORGANIC CHEMISTRY,79(8),3559-3571.
MLA	Fa, Shi-Xin,et al."Synthesis, Structure, and Fullerene-Complexing Property of Azacalix[6]aromatics".JOURNAL OF ORGANIC CHEMISTRY 79.8(2014):3559-3571.