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Issue 32, 2017
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Controlling the distance between hydrogen-bonded chloro-s-triazine tapes: crystal engineering using N-alkyl chains and the influence of temperature

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Abstract

The bis-N-alkyl-chlorotriazines show a strong tendency to form one-dimensional hydrogen-bonded tapes in the solid state. We predicted that increasing the alkyl chain length in the simplest tape-forming molecule would enable a controlled increase of the inter-tape spacing in the crystalline state. A series of bis-N-alkyl groups from bis-N-ethyl to bis-N-pentyl were synthesised and structurally characterised using single-crystal and powder X-ray diffraction at low temperature and ambient temperature. At low temperature the alkyl chains are rarely linear, instead adopting a variety of conformations to achieve close packing. Despite this variation, there is still a strong correlation of alkyl chain length with the inter-tape spacing in a single direction in the crystal. This correlation is strongest at ambient temperature where the longer chains are highly disordered and extended. We observe an “odd-number carbon” effect where bis-N-propyl 1b and bis-N-pentyl 1d derivatives undergo a structural phase transition with temperature.

Graphical abstract: Controlling the distance between hydrogen-bonded chloro-s-triazine tapes: crystal engineering using N-alkyl chains and the influence of temperature

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Publication details

The article was received on 05 Jun 2017, accepted on 21 Jul 2017 and first published on 21 Jul 2017


Article type: Paper
DOI: 10.1039/C7CE01049D
Citation: CrystEngComm, 2017,19, 4749-4758
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    Controlling the distance between hydrogen-bonded chloro-s-triazine tapes: crystal engineering using N-alkyl chains and the influence of temperature

    V. R. Aldilla, M. Bhadbhade, S. Bhattacharyya, N. Kumar, A. M. Rich and C. E. Marjo, CrystEngComm, 2017, 19, 4749
    DOI: 10.1039/C7CE01049D

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