Issue 71, 2004

Incorporation of sulfonate dyes into hydrogen-bonded networks

Abstract

The reaction of [C(NH2)3]Cl with methyl orange, Na[O3SC6H4N[double bond, length as m-dash]NC6H4NMe2], leads to formation of [C(NH2)3][O3SC6H4N[double bond, length as m-dash]NC6H4NMe2] 1 in which the sulfonate dye has been incorporated into a guanidinium sulfonate hydrogen-bonded bilayer sheet structure. Similar reactions with substituted guanidinium cations give [C(NH2)2(NHMe)][O3SC6H4N[double bond, length as m-dash]NC6H4NMe2]·MeOH 2·MeOH, [C(NH2)2(NHEt)][O3SC6H4N[double bond, length as m-dash]NC6H4NMe2] 3 and [C(NH2)2(NMe2)][O3SC6H4N[double bond, length as m-dash]NC6H4NMe2] 4. Although substitution disrupts formation of the GS sheets, the gross structures of 2–4 all have pseudo-bilayer structures, with similar gross features to 1. Compound 1 reacts with HCl in solution to generate the zwitterionic compound O3SC6H4NH[double bond, length as m-dash]NC6H4NMe25, but solid samples of 1 react reversibly with HCl gas to give the HCl adduct 1a. This interconversion has been studied by powder X-ray diffraction, IR spectroscopy and diffuse reflectance visible spectroscopy.

Graphical abstract: Incorporation of sulfonate dyes into hydrogen-bonded networks

Article information

Article type
Paper
Submitted
04 may. 2004
Accepted
11 jun. 2004
First published
17 sep. 2004

CrystEngComm, 2004,6, 429-436

Incorporation of sulfonate dyes into hydrogen-bonded networks

N. J. Burke, A. D. Burrows, M. F. Mahon and S. J. Teat, CrystEngComm, 2004, 6, 429 DOI: 10.1039/B406614F

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