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Issue 1, 2016
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Hydrogen-bonding networks of purine derivatives and their bilayers for guest intercalation

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Abstract

Two purine derivatives, 6-chloro-9-propyl-purin-2-amine (pr-GCl) and 6-chloro-9-pentyl-purin-2-amine (pt-GCl) have been synthesized and their crystal structures were determined by single crystal X-ray diffraction analyses. The purine rings in pr-GCl or pt-GCl form unique two-dimensional hydrogen-bonding networks which in turn stack via π–π interactions to give bilayers covered with alkyl chains. In pt-GCl, the pentyl groups interact effectively among themselves so that void space for guest molecules is not available. In contrast, pr-GCl can form host–guest co-crystals. Nuclear magnetic resonance (NMR) analyses of the pr-GCl crystals immersed in various solvents for up to 60 min indicate that aromatic molecules (benzene, xylene isomers) are better guests than aliphatic ones (n-hexane, cyclohexane, isooctane) in terms of their inclusion time and amount. Powder X-ray diffraction (PXRD) patterns for the guest-included pr-GCl crystals are quite different from the simulated one, supporting the guest diffusion into the pr-GCl crystals. The crystal structure of p-xylene@pr-GCl reveals that p-xylene molecules are intercalated between the characteristic pr-GCl bilayers that are shown in both pr-GCl and pt-GCl crystals.

Graphical abstract: Hydrogen-bonding networks of purine derivatives and their bilayers for guest intercalation

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Supplementary files

Article information


Submitted
11 Aug 2015
Accepted
07 Nov 2015
First published
09 Nov 2015

CrystEngComm, 2016,18, 62-67
Article type
Paper
Author version available

Hydrogen-bonding networks of purine derivatives and their bilayers for guest intercalation

Y. Jang, S. Y. Yoo, H. R. Gu, Y. J. Lee, Y. S. Cha, L. You, K. Noh and J. Kim, CrystEngComm, 2016, 18, 62
DOI: 10.1039/C5CE01611H

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