TY - JOUR
T1 - Macroscopic helical and cylindrical morphologies from achiral 1,3-diynes
AU - Lindsell, W. Edward
AU - Preston, Peter N.
AU - Seddon, John M.
AU - Rosair, Georgina M.
AU - Woodman, T. A J
PY - 2000/6
Y1 - 2000/6
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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0033799487&partnerID=8YFLogxK
U2 - 10.1021/cm000172v
DO - 10.1021/cm000172v
M3 - Article
SN - 0897-4756
VL - 12
SP - 1572
EP - 1576
JO - Chemistry of Materials
JF - Chemistry of Materials
IS - 6
ER -