Azulene appended cellulose: Synthesis, optical and chiroptical properties, film formation by electrochemical oxidation

  • Redl F
  • Kothe O
  • Rockl K
 et al. 
  • 1

    Readers

    Mendeley users who have this article in their library.
  • N/A

    Citations

    Citations of this article.

Abstract

Regioselective synthesis using protecting-group strategy yields azulene-cellulose conjugates 6-(azulene-2-carboxylate)-2,3-di-O-methyl cellulose AzC-1, 6-(4-azulene-1-yl-benzoate)-2,3-di-O-methyl cellulose AzC-2, and 6-(azulene-1-carboxylate)-2,3-di-O-methyl cellulose AzC-3. The spectral and electrochemical properties were investigated and compared with the azulene alkylesters 1b, 2b, and 3b. The relative fluorescence quantum yield of methyl 2-azulenecarboxylate 1b exceeds that of azulene cellulose AzC-1 by an order of magnitude. Cellulose derivative AzC-3 exhibits weak dual emission around 400 nm and 520 nm at room temperature. The circular dichroism (CD) of AzC-1, AzC-2, and AzC-3 are reported. Intensity and feature of the CD signals depend on the degree of substitution (DS) as shown by AzC-1. The CD-split signals at 280 nm (3A1 transition of azulene) are likely to result from interacting azulene groups. A regular (helical) structure of the cellulose backbone is postulated, leading to the (M)-configuration of the spatial azulene units. Unlike esters 2b and 3b azulene appended celluloses AzC-1 and AzC-2 electropolymerize under potentiodynamic conditions. Chemically modified electrodes : are formed. Dotation sates were characterized by UV-Vis-NIR-spectroelectrochemistry. Azulene appended celluloses are suitable for making conducting electrodes with chiral coating materials. ? Wiley-VCH Verlag GmbH, 2000.

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document

Authors

  • F.X. Redl

  • O. Kothe

  • K. Rockl

  • W. Bauer

  • J. Daub

Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free