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

Ryo Amemiya, Nozomi Saito, Masahiko Yamaguchi

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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°C at concentrations above 2 × 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.

Original languageEnglish
Pages (from-to)7137-7144
Number of pages8
JournalJournal of Organic Chemistry
Volume73
Issue number18
DOIs
Publication statusPublished - 2008 Sep 19

ASJC Scopus subject areas

  • Organic Chemistry

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