Sugar-dependent spectral responses of azobenzene glycopyranoside monolayers

Masahito Sano, Masato Amaike, Ayumi Kamino, Seiji Shinkai

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Novel amphiphilic glycopyranosides containing an azobenzene chromophore and an amide-benzene auxochrome are synthesized. A sugar headgroup is attached to the auxochrome unit that links directly to azobenzene. The UV-vis spectral response of the monolayer to a change of the molecular area is found to depend on the chemical structure of the sugar unit, α-D-glucopyranose or α-D-galactopyranose. When spread on the water surface at large molecular areas, both compounds show π-π* long-wavelength peaks at around 460 nm. Upon compression of the films, the peaks for the glucopyranoside exhibits a red shift, whereas that for the galactopyranoside gives a blue shift. A reference compound having a carboxylic acid in place of the sugar unit produces a blue shift because of the formation of H-like aggregates. The pressure isotherm and a morphological study suggest that a similar aggregation is responsible for the blue shift due to the galactopyranoside. FTIR spectroscopy indicates that the amide group of the glucopyranoside contains mostly the -C=N- resonance form. This resonance form increases the planarity of the azobenzeneamide-benzene units, resulting in the observed red shift. This study offers a basic chemical structure for systematic controls of dye aggregates by sugar.

Original languageEnglish
Pages (from-to)4367-4371
Number of pages5
JournalLangmuir
Volume17
Issue number14
DOIs
Publication statusPublished - Jul 10 2001
Externally publishedYes

Fingerprint

Azobenzene
sugars
spectral sensitivity
Sugars
Monolayers
Galactose
blue shift
Benzene
Amides
red shift
amides
benzene
Chromophores
Carboxylic Acids
surface water
Carboxylic acids
carboxylic acids
chromophores
Isotherms
isotherms

All Science Journal Classification (ASJC) codes

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

Cite this

Sano, M., Amaike, M., Kamino, A., & Shinkai, S. (2001). Sugar-dependent spectral responses of azobenzene glycopyranoside monolayers. Langmuir, 17(14), 4367-4371. https://doi.org/10.1021/la010187n

Sugar-dependent spectral responses of azobenzene glycopyranoside monolayers. / Sano, Masahito; Amaike, Masato; Kamino, Ayumi; Shinkai, Seiji.

In: Langmuir, Vol. 17, No. 14, 10.07.2001, p. 4367-4371.

Research output: Contribution to journalArticle

Sano, M, Amaike, M, Kamino, A & Shinkai, S 2001, 'Sugar-dependent spectral responses of azobenzene glycopyranoside monolayers', Langmuir, vol. 17, no. 14, pp. 4367-4371. https://doi.org/10.1021/la010187n
Sano, Masahito ; Amaike, Masato ; Kamino, Ayumi ; Shinkai, Seiji. / Sugar-dependent spectral responses of azobenzene glycopyranoside monolayers. In: Langmuir. 2001 ; Vol. 17, No. 14. pp. 4367-4371.
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