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

Research output: Contribution to journalArticle

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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Diynes
Anhydrides
Triazines
Chirality
Organic solvents
Precipitates
Crystal structure
Crystalline materials
X ray diffraction
Scanning electron microscopy

Cite this

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
Lindsell, W. Edward ; Preston, Peter N. ; Seddon, John M. ; Rosair, Georgina M. ; Woodman, T. A J. / Macroscopic helical and cylindrical morphologies from achiral 1,3-diynes. In: Chemistry of Materials. 2000 ; Vol. 12, No. 6. pp. 1572-1576.
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title = "Macroscopic helical and cylindrical morphologies from achiral 1,3-diynes",
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 {\AA} 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) {\AA}, b = 8.0690(10) {\AA}, c = 29.524(3) {\AA}; 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.",
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Lindsell, WE, Preston, PN, Seddon, JM, Rosair, GM & Woodman, TAJ 2000, 'Macroscopic helical and cylindrical morphologies from achiral 1,3-diynes', Chemistry of Materials, vol. 12, no. 6, pp. 1572-1576. https://doi.org/10.1021/cm000172v

Macroscopic helical and cylindrical morphologies from achiral 1,3-diynes. / Lindsell, W. Edward; Preston, Peter N.; Seddon, John M.; Rosair, Georgina M.; Woodman, T. A J.

In: Chemistry of Materials, Vol. 12, No. 6, 06.2000, p. 1572-1576.

Research output: Contribution to journalArticle

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AU - Lindsell, W. Edward

AU - Preston, Peter N.

AU - Seddon, John M.

AU - Rosair, Georgina M.

AU - Woodman, T. A J

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N2 - 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.

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Lindsell WE, Preston PN, Seddon JM, Rosair GM, Woodman TAJ. Macroscopic helical and cylindrical morphologies from achiral 1,3-diynes. Chemistry of Materials. 2000 Jun;12(6):1572-1576. https://doi.org/10.1021/cm000172v