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Issue 9, 2015
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Spectral fine tuning of cyanine dyes: electron donor–acceptor substituted analogues of thiazole orange

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Abstract

The introduction of electron donor and acceptor groups at strategic locations on a fluorogenic cyanine dye allows fine-tuning of the absorption and emission spectra while preserving the ability of the dye to bind to biomolecular hosts such as double-stranded DNA and a single-chain antibody fragment originally selected for binding to the parent unsubstituted dye, thiazole orange (TO). The observed spectral shifts are consistent with calculated HOMO–LUMO energy gaps and reflect electron density localization on the quinoline half of TO in the LUMO. A dye bearing donating methoxy and withdrawing trifluoromethyl groups on the benzothiazole and quinoline rings, respectively, shifts the absorption spectrum to sufficiently longer wavelengths to allow excitation at green wavelengths as opposed to the parent dye, which is optimally excited in the blue.

Graphical abstract: Spectral fine tuning of cyanine dyes: electron donor–acceptor substituted analogues of thiazole orange

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Article information


Submitted
25 Mar 2015
Accepted
02 Jul 2015
First published
14 Jul 2015

Photochem. Photobiol. Sci., 2015,14, 1703-1712
Article type
Paper
Author version available

Spectral fine tuning of cyanine dyes: electron donor–acceptor substituted analogues of thiazole orange

E. E. Rastede, M. Tanha, D. Yaron, S. C. Watkins, A. S. Waggoner and B. A. Armitage, Photochem. Photobiol. Sci., 2015, 14, 1703
DOI: 10.1039/C5PP00117J

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