NDLI: Synthesis, Structure and Molecular Recognition of Functionalised Tetraoxacalix[2]arene[2]triazines

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Synthesis, Structure and Molecular Recognition of Functionalised Tetraoxacalix[2]arene[2]triazines

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Synthesis, Structure and Molecular Recognition of Functionalised Tetraoxacalix[2]arene[2]triazines

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Wang, Qi-qiang Wang, Mei-xiang Huang, Zhi-tang Wang, De-xian Yang, Hai-bo
Description	Author Affiliation: Wang QQ ( Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P.R. China.)
Abstract	Functionalised 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 13 b, 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–π and CH⋅⋅⋅π interactions, were found to be the driving force for the formation of host–guest complexes.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	24
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-06-25
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Calixarenes Chemistry Chemical Synthesis Macrocyclic Compounds Triazines Crystallography, X-Ray Hydrogen Bonding Magnetic Resonance Spectroscopy Models, Molecular Molecular Conformation Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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