Issue 36, 2014

Effect of head group size on the photoswitching applications of azobenzene Disperse Red 1 analogues

Abstract

We investigate the effect of the increased molecular bulk in the ‘head’ group for a class of newly synthesized azobenzene chromophores with a clickable ethynyl group para and a nitro group ortho to the azo bond on the distal benzene ring. This ‘variable-head’ functionalization provides a family of dyes with photophysical characteristics very similar to those of Disperse Red 1, one of the most commonly used azo dyes in materials science. Phenyl, naphthyl, and anthracyl derivatives were synthesized as small molecules, monomers, homopolymers, and copolymers in a rapid and facile manner using click chemistry, confirming the versatility of this parent chromophore. Photochemical and spectral studies indicate that this strategy is suitable to build a ‘bulkiness series’ of stimuli-responsive materials, as the various material derivatives retain the absorption and kinetic characteristics of the parent chromophore necessary for all optical patterning applications that DR1 dyes have been optimized for. In thin films, larger head group size was found to increase the stability of light-induced birefringence in copolymers. The homopolymers formed stable surface-relief gratings upon interference irradiation, whose grating depths correlate with head group size, demonstrating that this new class of polymers can also undergo tailored macroscopic photoinduced motions, which could have applications in all optical nano-patterning.

Graphical abstract: Effect of head group size on the photoswitching applications of azobenzene Disperse Red 1 analogues

Supplementary files

Article information

Article type
Paper
Submitted
13 touko 2014
Accepted
13 heinä 2014
First published
15 heinä 2014

J. Mater. Chem. C, 2014,2, 7505-7512

Author version available

Effect of head group size on the photoswitching applications of azobenzene Disperse Red 1 analogues

A. Goulet-Hanssens, T. C. Corkery, A. Priimagi and C. J. Barrett, J. Mater. Chem. C, 2014, 2, 7505 DOI: 10.1039/C4TC00996G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements