Synthesis of 1,128-Octacosahectanediol and Its Sharp Thermoresponse in Solution with Concomitant Structural Change

Nozomi Saito, Yasuhiro Shinozaki, Masanori Shigeno, Kumiko Mushiake, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

1,128-Octacosahectanediol, which has an extremely long polymethylene chain, was synthesized. The heptaene C128 intermediate with both ends silylated was synthesized by the sequence of the Wittig reaction and acetal deprotection in a two-directional manner. The unsaturated compound was converted to a saturated disilyl ether by homogeneous hydrogenation under toluene reflux, and was subsequently desilylated under THF/toluene/12 M HCl refluxing conditions to yield a C128 diol. High-temperature conditions were employed to dissolve the substrates, and cooling liberated the products, which were isolated by filtration. 1,128-Octacosahectanediol showed a sharp increase in solubility in organic solvents with temperature changes of 10 K along with thermal hysteresis, which was ascribed to the concomitant structural change. The extended structure in the solid state was converted to a globular structure in solution, which involved large enthalpic loss and entropic gain.

Original languageEnglish
Pages (from-to)8459-8464
Number of pages6
JournalChemistrySelect
Volume2
Issue number27
DOIs
Publication statusPublished - 2017 Sep 21

Keywords

  • conformation change
  • diol
  • long-chain alkane
  • solubility
  • temperature dependence

ASJC Scopus subject areas

  • Chemistry(all)

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