Convenient preparation of self-assembled monolayers derived from calix[4]resorcinarene derivatives exhibiting resistance to desorption

Kunihiro Ichimura, Sang Keun Oh, Masanori Fujimaki, Yoko Matsuzawa, Masaru Nakagawa

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Crown conformers of O-carboxymethylated calix[4]resorcinarenes (CRA-CMs) bearing four perfluorooctyl-and octylazobenzene residues at the lower rim of the cyclic skeleton were synthesized to investigate the resistance to desorption of CRA-CMs forming self-assembled monolayers on aminosilylated silica substrates and the surface energy photocontrol based on E-to-Z photoisomerization of the azobenzene moiety. In comparison with CRA-CM monolayers on silica substrates, the desorption of CRA-CMs on the aminated substrate was remarkably suppressed even when CRA-CM monolayers were sonicated in polar solvents and even in water. The high desorption-resistance was attributable to multi-point adsorption of CRA-CMs through COOH/NH2 interactions. UV-Vis spectral studies revealed that CRA-CM substituted with p-octylazobenzene exhibited high E-to-Z photoisomerizability up to 92% in self-assembled monolayers, while less photoisomerizability was observed for CRA-CM bearing p-perfluorooctylazobenzenes due to the steric hindrance of the larger perfluoroalkyl chains. Photoinduced changes of contact angles for water up to 8.3° were observed for a CRA-CM monolayer.

Original languageEnglish
Pages (from-to)173-183
Number of pages11
JournalJournal of Inclusion Phenomena
Volume35
Issue number1-2
Publication statusPublished - 1999 Oct 1
Externally publishedYes

Keywords

  • Aminosilanization
  • Calix[4]resorcinarene
  • Chemisorption
  • Photoisomerization
  • Self-assembled monolayer

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

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