Monolayer Formation Properties of Cholesterol-Based Azobenzene Amphiphiles with the Natural and the Inverted C3 Configuration

Hirosuke Kawabata, Kazutaka Murata, Takaaki Harada, Seiji Shinkai

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The monolayer formation properties of cholesterol-based azobenzene amphiphiles with the natural (SI-CS configuration (Is) and the inverted (R)-C3 configuration (1r) were examined at the air—water interface. The computational study reveals that Is adopts an extended conformation whereas 1R adopts an L-shaped bent conformation. Is gave an expanded phase with Ao (limiting area) = 0.60 nm2 molecule-1 and Ai (lift-off area) = 0.64 nm2 molecule-1 whereas 1r gave a condensed phase with Ao = 0.49 nm2 molecule-1 and Ai = 0.54 nm2 molecule-1. Examination using reflectance spectroscopy established that Is forms a monolayer with a J-aggregation mode (λmax 407 nm) and with an increase in the compressibility it changes to an H-aggregation mode (Amax 336 nm) whereas 1r forms a monolayer having a Amax (362 nm) comparable with the monomeric absorption maximum, indicating that the electronic interaction among the azobenzene moieties is absent. The morphological changes in the monolayers were directly observed by an optical microscope and reasonably correlated with the spectroscopic changes. The results indicate that the absolute configuration at C3 has a crucial influence on the aggregation properties of cholesterol-based amphiphiles in a monolayer system.

Original languageEnglish
Pages (from-to)623-626
Number of pages4
JournalLangmuir
Volume11
Issue number2
DOIs
Publication statusPublished - Jan 1 1995
Externally publishedYes

Fingerprint

Amphiphiles
Azobenzene
Cholesterol
cholesterol
Monolayers
configurations
Molecules
Agglomeration
molecules
Conformations
International System of Units
optical microscopes
compressibility
Compressibility
examination
reflectance
Microscopes
azobenzene
Spectroscopy
electronics

All Science Journal Classification (ASJC) codes

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

Cite this

Monolayer Formation Properties of Cholesterol-Based Azobenzene Amphiphiles with the Natural and the Inverted C3 Configuration. / Kawabata, Hirosuke; Murata, Kazutaka; Harada, Takaaki; Shinkai, Seiji.

In: Langmuir, Vol. 11, No. 2, 01.01.1995, p. 623-626.

Research output: Contribution to journalArticle

Kawabata, Hirosuke ; Murata, Kazutaka ; Harada, Takaaki ; Shinkai, Seiji. / Monolayer Formation Properties of Cholesterol-Based Azobenzene Amphiphiles with the Natural and the Inverted C3 Configuration. In: Langmuir. 1995 ; Vol. 11, No. 2. pp. 623-626.
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