Title

Solvatochromism in Diketopyrrolopyrrole Derivatives: Experimental and Computational Studies

Document Type

Article

Publication Date

9-2014

Publication Details

This article was originally published as:

Szabadai, R. S., Roth-Barton, J., Ghiggino, K. P., White, J. M., & Wilson, D. J. (2014). Solvatochromism in diketopyrrolopyrrole derivatives: Experimental and computational studies. Australian Journal of Chemistry, 67(9), 1330-1337. doi:10.1071/CH14057

ISSN:1445-0038

ANZSRC / FoR Code

030701 Quantum Chemistry

Abstract

A series of seven thiophen-substituted diketopyrrolopyrrole derivatives were synthesised and their solution absorption spectra characterised in a range of solvents of varying polarity. The absorption spectra of these diketopyrrolopyrrole derivatives exhibited significant negative solvatochromism. The behaviour is consistent with results of time-dependent density-functional theory calculations of excitation energies. Calculated electronic structures suggest that there is significant charge transfer between the electron-donating thiophen substituents and the diketopyrrolopyrrole core but that the magnitude of this charge shift is reduced in the excited state compared with the ground state. The resulting reduction in polarity of the excited state accounts for the negative solvatochromism observed. The implications of the results for the potential application of diketopyrrolopyrrole compounds as photovoltaic materials are considered.

Comments

Due to copyright restrictions this article is unavailable for download.

This article may be accessed from the publisher here.

At the time of writing David Wilson was affiliated with Avondale College as a Conjoint Lecturer.