Azacalix[7]arene heptamethyl ether: preparation, nanochannel crystal structure, and selective adsorption of carbon dioxide

The Journal of Organic Chemistry
Hirohito TsueRui Tamura

Abstract

To investigate the solid-state complexation of nitrogen-bridged calixarene analogues, azacalix[7]arene heptamethyl ether 1 has been prepared by applying a "5 + 2"-fragment coupling approach using Buchwald-Hartwig aryl amination reaction aided by our previously devised temporal N-silylation protocol. X-ray crystallographic analysis revealed that azacalix[7]arene 1 adopted a highly distorted 1,2-alternate conformation in the solid state as a result of intramolecular NH/O hydrogen bonding interactions and steric repulsion between the methoxy groups. In the crystal, molecules of 1 are mutually interacted by intermolecular NH/O and CH/pi interactions to establish one-dimensional (1D) hexane-filled nanochannel crystal architecture. Similarly to our recently reported azacalix[6]arene 2, the desolvated crystalline powder material of 1 was capable of selectively and rapidly adsorbing CO2 among the four main components of the atmosphere. The adsorption capacity of 1 for CO2 nearly doubled as compared to that of 2 because of the formation of the 1D nanochannel with almost twice the volume of the latter.

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Citations

Aug 13, 2011·Chemical Communications : Chem Comm·Jean-Manuel RaimundoOlivier Siri
Aug 25, 2015·The Journal of Organic Chemistry·Wen-Sheng RenMei-Xiang Wang
Oct 28, 2009·The Journal of Organic Chemistry·En-Xuan ZhangMei-Xiang Wang
Jan 2, 2010·The Journal of Organic Chemistry·Li-Xia WangMei-Xiang Wang
Apr 24, 2021·The Journal of Organic Chemistry·Ikuko MiyoshiTetsutaro Hattori
Sep 4, 2010·Organic Letters·Jeffrey L Katz, Brittany A Tschaen
Sep 28, 2010·Journal of the American Chemical Society·Wenbin YangMartin Schröder
Dec 7, 2010·Organic Letters·Wim Van RossomWouter Maes
Mar 25, 2014·The Journal of Organic Chemistry·Shi-Xin FaMei-Xiang Wang
Feb 1, 2018·The Journal of Organic Chemistry·Naoya MorohashiTetsutaro Hattori

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