Hetero-double-helix formation by an ethynylhelicene oligomer possessing perfluorooctyl side chains

The Journal of Organic Chemistry
Ryo AmemiyaMasahiko Yamaguchi

Abstract

Monomeric to pentameric (P)-ethynylhelicene oligomers possessing perfluorooctyl side chains were synthesized. The circular dichroism (CD) and vapor pressure osomometry (VPO) studies indicated the formation of a helix-dimer for the (P)-pentamer, for example, in trifluoromethylbenzene at 5 degrees C at concentrations above 2 x 10(-6) M. Compared with a (P)-pentamer possessing decyloxycarbonyl side chains, the perfluorooctyl (P)-pentamer exhibited lower solubilities in organic solvents, formed a thermodynamically more stable helix-dimer, and exhibited a mirror image CD spectrum. The perfluorooctyl (P)-pentamer formed a hetero-helix dimer with a decyloxycarbonyl (M)-pentamer but not with a (P)-pentamer. It indicated higher stability of the hetero-helix dimer over the homo-helix dimers.

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Citations

Oct 25, 2011·Chemical Reviews·Yun Shen, Chuan-Feng Chen
Jul 10, 2012·Inorganic Chemistry·Celedonio M ÁlvarezDaniel Miguel
May 10, 2012·Journal of the American Chemical Society·Hidekazu YamadaEiji Yashima
May 6, 2011·The Journal of Organic Chemistry·Nozomi SaitoMasahiko Yamaguchi
Nov 1, 2012·The Journal of Organic Chemistry·Wataru IchinoseMasahiko Yamaguchi
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Feb 1, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nozomi Saito, Masahiko Yamaguchi
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Nov 13, 2009·Chemical Reviews·Eiji YashimaKanji Nagai
Jun 15, 2021·Chemical Science·Luca Gabrielli, Christopher A Hunter

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