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Photophysical properties of an extended bis-oxonol dye

Lookup NU author(s): Professor Andrew Benniston, Emeritus Professor Anthony Harriman, Iain McCulloch, Maryam Mehrabi, Sarah Rostron, Craig Sams

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Abstract

A bis-oxonol dye has been prepared from reaction between N,N′-dibutylthiobarbituric acid and glutacondialdehyde dianil monohydrochloride. The dye comprises two N,N′-dibutylthiobarbiturate units connected via a pentamethine spacer, and detailed 1H NMR (2D-COSY, NOESY) experiments confirm that the polyene backbone is in the all- trans arrangement. The dye is intensely blue in colour, absorbing around 640 nm in ethanol with a molar absorption coefficient of 175,000 mol-1 dm3 cm-1. Under illumination, the first-excited all-trans singlet state is formed but suprisingly there is little or no isomerisation to a cis isomer. Quantum chemical calculations suggest that there is a high barrier to isomerisation in the ground state while the absence of photoisomerisation is attributed to ineffective population of the relevant LUMO at the S1 level. The dye, which possesses an unusually long-lived singlet excited state for a cyanine-type dye, shows modest capacity for transporting potassium cations across a membrane and functions as an excellent acceptor for electronic energy transfer from other cyanine dyes. © 2004 Elsevier B.V. All rights reserved.

Publication metadata

Author(s): Benniston AC, Harriman A, McCulloch IE, Mehrabi M, Rostron SA, Sams CA

Publication type: Article

Publication status: Published

Journal: Journal of Photochemistry and Photobiology A: Chemistry

Year: 2004

Volume: 163

Issue: 1-2

Pages: 61-67

ISSN (print): 1010-6030

ISSN (electronic): 1873-2666

Publisher: Elsevier SA

URL: http://dx.doi.org/10.1016/S1010-6030(03)00433-7

DOI: 10.1016/S1010-6030(03)00433-7

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