Incorporation of sulfonate dyes into hydrogen-bonded networks

N J Burke, A D Burrows, M F Mahon, S J Teat

Research output: Contribution to journalArticle

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Abstract

The reaction of [C(NH2)(3)] Cl with methyl orange, Na[O3SC6H4N=NC6H4NMe2], leads to formation of [C(NH2)(3)][O3SC6H4N=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=NC6H4NMe2].MeOH2.MeOH, [C(NH2)(2)(NHEt)][O3SC6H4N=NC6H4NMe2] 3 and [C(NH2)(2)(NMe2)][O3SC6H4N=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=NC6H4NMe2 5, 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.
Original languageEnglish
Pages (from-to)429-436
Number of pages8
JournalCrystEngComm
Volume6
DOIs
Publication statusPublished - 2004

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Guanidine
sulfonates
X ray powder diffraction
Hydrogen
Infrared spectroscopy
Substitution reactions
Coloring Agents
Dyes
dyes
Positive ions
Spectroscopy
zwitterions
hydrogen
Gases
spectroscopy
adducts
Cations
substitutes
reflectance
cations

Cite this

Incorporation of sulfonate dyes into hydrogen-bonded networks. / Burke, N J; Burrows, A D; Mahon, M F; Teat, S J.

In: CrystEngComm, Vol. 6, 2004, p. 429-436.

Research output: Contribution to journalArticle

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abstract = "The reaction of [C(NH2)(3)] Cl with methyl orange, Na[O3SC6H4N=NC6H4NMe2], leads to formation of [C(NH2)(3)][O3SC6H4N=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=NC6H4NMe2].MeOH2.MeOH, [C(NH2)(2)(NHEt)][O3SC6H4N=NC6H4NMe2] 3 and [C(NH2)(2)(NMe2)][O3SC6H4N=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=NC6H4NMe2 5, 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.",
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AU - Burke, N J

AU - Burrows, A D

AU - Mahon, M F

AU - Teat, S J

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N2 - The reaction of [C(NH2)(3)] Cl with methyl orange, Na[O3SC6H4N=NC6H4NMe2], leads to formation of [C(NH2)(3)][O3SC6H4N=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=NC6H4NMe2].MeOH2.MeOH, [C(NH2)(2)(NHEt)][O3SC6H4N=NC6H4NMe2] 3 and [C(NH2)(2)(NMe2)][O3SC6H4N=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=NC6H4NMe2 5, 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.

AB - The reaction of [C(NH2)(3)] Cl with methyl orange, Na[O3SC6H4N=NC6H4NMe2], leads to formation of [C(NH2)(3)][O3SC6H4N=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=NC6H4NMe2].MeOH2.MeOH, [C(NH2)(2)(NHEt)][O3SC6H4N=NC6H4NMe2] 3 and [C(NH2)(2)(NMe2)][O3SC6H4N=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=NC6H4NMe2 5, 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.

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