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A general and high yielding fragment coupling synthesis of heteroatom-bridged calixarenes and the unprecedented examples of calixarene cavity fine-tuned by bridging heteroatoms
Wang, MX; Yang, HB
2004-12-01
Source PublicationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN0002-7863
Volume126Issue:47Pages:15412-15422
AbstractA number of aza- and/or oxo-bridged calix[2]arene[2]triazines have been synthesized through an unusually high yielding and efficient fragment coupling approach starting from cyanuric chloride and resorcinol, 3-aminophenol, m-phenylenediamine, and N,N'-dimethyl-m-phenylenediamine. These novel macrocycles, which belong to the next generation of calixarenes or cyclophanes, form a unique cavity that is resulted from two isolated benzene planes and two bis-heteroatom-conjugated triazine planes in a 1,3-alternate fashion. The nature of the bridging heteroatoms, i.e., combination of the electronic, conjugative, and steric effects of the nitrogen and oxygen atoms, strongly regulates the cavity size, generating a set of fine-tuned cavities in which the distance between two benzene rings at the upper rim ranges from 5.011 to 7.979 Angstrom. The multiple intermolecular hydrogen bond interactions among N,N'-dimethylated tetraazacalix[2]arene[2]triazines and among tetraazacalix[2]arene[2]triazines lead to the formation of infinite one-dimensional chain structure and two-dimensional zigzag layered structure, respectively, in the solid state. The ease of preparation and further chemical manipulations, and the readily tunable cavity structures render these aza- and/or oxo-bridged calix[2]arene[2]triazines the unique platforms in the study of supramolecular chemistry.
DOI10.1021/ja0465092
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000225349800044
PublisherAMER CHEMICAL SOC
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Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/82190
Collection中国科学院化学研究所
Corresponding AuthorWang, MX
AffiliationChinese Acad Sci, Inst Chem, Ctr Mol Sci, Biol Chem Lab, Beijing 100080, Peoples R China
Recommended Citation
GB/T 7714
Wang, MX,Yang, HB. A general and high yielding fragment coupling synthesis of heteroatom-bridged calixarenes and the unprecedented examples of calixarene cavity fine-tuned by bridging heteroatoms[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2004,126(47):15412-15422.
APA Wang, MX,&Yang, HB.(2004).A general and high yielding fragment coupling synthesis of heteroatom-bridged calixarenes and the unprecedented examples of calixarene cavity fine-tuned by bridging heteroatoms.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,126(47),15412-15422.
MLA Wang, MX,et al."A general and high yielding fragment coupling synthesis of heteroatom-bridged calixarenes and the unprecedented examples of calixarene cavity fine-tuned by bridging heteroatoms".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 126.47(2004):15412-15422.
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