Issue 19, 2007
From the journal:

Journal of Materials Chemistry

Design principles to tune the optical properties of 1,3,4-oxadiazole-containing molecules†

Onas Boltona  and  Jinsang Kim*ab  

* Corresponding authors

a Department of Materials Science and Engineering, University of Michigan, Ann Arbor, MI, USA

b Departments of Chemical Engineering, Macromolecular Engineering, and Biomedical Engineering, University of Michigan, Ann Arbor, MI, USA
E-mail: jinsang@umich.edu
Fax: +1-734-763-4788
Tel: +1-734-936-4681

Abstract

We have synthesized a series of oxadiazole compounds and ethynylene analogs. Our data reveal that the ring is both optically transparent in the visible range and fully conjugating while we have also discovered the presence of a non-radiative mechanism active in molecules containing common para-dialkoxy substituents adjacent to the oxadiazole ring(s). This structure leads to a greatly reduced quantum yield, in our example dropping from 95.0% to 48.0%. Through our thorough study we have revealed evidence that this is the result of a repulsive interaction between the oxadiazole and the adjacent alkoxy oxygen atom, which we believe prevents excited-state planarity. This quantum yield reduction is preventable through the design principles presented here.

Graphical abstract: Design principles to tune the optical properties of 1,3,4-oxadiazole-containing molecules

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Article information

DOI
https://doi.org/10.1039/B616996A
Article type
Paper
Submitted
21 Nov 2006
Accepted
11 Jan 2007
First published
30 Jan 2007

J. Mater. Chem., 2007,17, 1981-1988

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Design principles to tune the optical properties of 1,3,4-oxadiazole-containing molecules

O. Bolton and J. Kim, J. Mater. Chem., 2007, 17, 1981 DOI: 10.1039/B616996A

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