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1 April 2000 Structural and Environmental Requirements for Quenching of Singlet Oxygen by Cyanine Dyes
Jeffrey R. Kanofsky, Paul D. Sima
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Singlet-oxygen quenching constants were measured for 19 cyanine dyes in acetonitrile. The most efficient quenchers were 1-butyl-2-[2-[3-[(1-butyl-6-chlorobenz[cd]indol-2(1H)-ylidene)ethylidene]-2-chloro-1-cyclohexen-1-yl]ethenyl]-6-chlorobenz[cd]indolium and 6-chloro-2-[2-[3-(6-chloro-1-ethylbenz[cd]indol-2(1H)-ylidene)ethylidene]-2-phenyl-1-cyclopenten-1-yl]ethenyl]-1-ethylbenz[cd]indolium, having quenching constants with diffusion-controlled values of 2.0 ± 0.1 × 1010 and 1.5 ± 0.1 × 1010 M−1 s−1, respectively. There was a trend toward increased quenching constants for cyanine dyes with the absorption band maxima at longer wavelengths. However, the quenching constants correlated better with the oxidation potentials of the cyanine dyes, suggesting that quenching proceeds by charge transfer rather than energy transfer. The quenching constants for 1,1′,3,3,3′,3′-hexamethylindotricarbocyanine perchlorate and 1,1′-diethyl-4,4′-carbocyanine iodide were measured in several solvents as well as in aqueous solutions of detergent micelles. In different solvents, the quenching constants varied by as much as a factor of 50. The quenching constants were largest in solvents with the highest values on the π* scale of Kamlet, Abboud, Abraham and Taft. This was consistent with quenching occurring by charge transfer. Within cells, cyanine dyes concentrate in membrane-bound organelles. The quenching constants were substantial within detergent micelles. To the extent that micelles are models for biological membranes, cyanine dyes may be effective biological singlet-oxygen quenchers.

Jeffrey R. Kanofsky and Paul D. Sima "Structural and Environmental Requirements for Quenching of Singlet Oxygen by Cyanine Dyes," Photochemistry and Photobiology 71(4), 361-368, (1 April 2000).<0361:SAERFQ>2.0.CO;2
Received: 15 September 1999; Accepted: 1 December 1999; Published: 1 April 2000

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