Macroscopic helical and cylindrical morphologies from achiral 1,3-diynes

W. Edward Lindsell, Peter N. Preston, John M. Seddon, Georgina M. Rosair, T. A J Woodman

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29 Citations (Scopus)

Abstract

Diacetylenes containing an anhydride function (1) or two s-triazine groups (2) precipitate from organic solvents in large helical or cylindrical forms, respectively, which have been studied by optical and scanning electron microscopy. X-ray diffraction studies on helices of 10,12-tricosadynoic anhydride, {n-C10H21C=C-C=C(CH2)8CO}2O (1), show a lamellar crystalline phase with layer spacing of 42.5 ± 0.5 Å and support a noninterdigitated bilayer structure. The crystal structure of a related amphiphilic diacetylene, n-C10H21C=C-C= C(CH2)8CH2OSO2C6H4Me-4 (3), is also reported and discussed: triclinic, P1, a = 5.9730(10) Å, b = 8.0690(10) Å, c = 29.524(3) Å; a = 95.020(10)°, ß = 93.260(10)°, ? = 97.480(10)°. The nonamphiphilic, a,?-difunctionalized diacetylene, 6,6'-(deca-4,6-diyne-1,10-diyl)di-2,4-diamino-1,3,5-triazine, 2-{4,6-(NH2)2C3N3}(CH2)3C=C-C=C(CH2)3-{C3N3(NH2)2-4,6}-2 (2), forms solid cylindrical particles of mean length ~0.5 mm, which may derive from helix formation. The origin of macroscopic chirality in the solid-state morphology of the achiral anhydride (1) is discussed.

Original languageEnglish
Pages (from-to)1572-1576
Number of pages5
JournalChemistry of Materials
Volume12
Issue number6
DOIs
Publication statusPublished - Jun 2000

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    Lindsell, W. E., Preston, P. N., Seddon, J. M., Rosair, G. M., & Woodman, T. A. J. (2000). Macroscopic helical and cylindrical morphologies from achiral 1,3-diynes. Chemistry of Materials, 12(6), 1572-1576. https://doi.org/10.1021/cm000172v