Synthesis, Structure and Molecular Recognition of Functionalised Tetraoxacalix[2]arene[2]triazines
Wang, Qi-Qiang1; Wang, De-Xian1; Yang, Hai-Bo1; Huang, Zhi-Tang1; Wang, Mei-Xiang1,2
AbstractFunctionalised dialkoxy-substituted tetraoxacalix[2]arene[2]triazine macrocycles 6 have been readily synthesised by the fragment coupling approach using methyl 3,5-dihydroxy-4-alkoxybenzoates and cyanuric chloride as the starting materials under very mild conditions. AlCl(3)-mediated deallylation and debenzylation reactions afforded the lower-rim dihydroxy-substituted tetraoxacalix[2]arene[2]triazine derivatives 11 and 13 in good yields. Although dialkoxy-substituted tetraoxacalix[2]arene[2]triazine macrocycles are fluxional in solution on the NMR spectroscopy timescale, they adopt a symmetric or slightly distorted 1,3-alternate conformation with the bridging oxygen atoms conjugated with the triazine rings. The dihydroxylated tetraoxacalix[2]arene[2]triazine 13b, which gives a mixture of monomer and dimer in solution according to a diffusion NMR spectroscopy study, adopts a 1,3-alternate conformation and forms a cyclic tetrameric assembly in the solid state due to the formation of intermolecular hydrogen-bonding networks. This dihydroxylated macrocyclic host molecule, a hydrogen-bond donor macrocycle with a V-shaped cleft, interacts with 2,2'-bipyridine, 4,4'-bipyridine and 1,10-phenanthroline guests. Although in solution they form the corresponding 1:1 complexes with binding constants ranging from 37.7 to 213 M(-1), 2:2 host-guest complexes were observed in the crystalline state. Hydrogen-bonding interactions, along with other non-covalent interactions, such as lone-pair-electron-pi and C-H center dot center dot center dot pi interactions, were found to be the driving force for the formation of host-guest complexes.
KeywordCalixarenes Host-guest Systems Hydrogen Bonds Molecular Recognition Structure Elucidation
Indexed BySCI ; IC
WOS IDWOS:000279856300026
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Cited Times:51[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Corresponding AuthorWang, De-Xian
Affiliation1.Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
2.Tsinghua Univ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Dept Chem, Beijing 100084, Peoples R China
Recommended Citation
GB/T 7714
Wang, Qi-Qiang,Wang, De-Xian,Yang, Hai-Bo,et al. Synthesis, Structure and Molecular Recognition of Functionalised Tetraoxacalix[2]arene[2]triazines[J]. CHEMISTRY-A EUROPEAN JOURNAL,2010,16(24):7265-7275.
APA Wang, Qi-Qiang,Wang, De-Xian,Yang, Hai-Bo,Huang, Zhi-Tang,&Wang, Mei-Xiang.(2010).Synthesis, Structure and Molecular Recognition of Functionalised Tetraoxacalix[2]arene[2]triazines.CHEMISTRY-A EUROPEAN JOURNAL,16(24),7265-7275.
MLA Wang, Qi-Qiang,et al."Synthesis, Structure and Molecular Recognition of Functionalised Tetraoxacalix[2]arene[2]triazines".CHEMISTRY-A EUROPEAN JOURNAL 16.24(2010):7265-7275.
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