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Issue 5, 2007
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Singlet oxygen generation using iodinated squaraine and squaraine-rotaxane dyes

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Abstract

The goal of this study was to assess the ability of squaraine-rotaxanes to generate singlet oxygen for potential application in photodynamic therapy (PDT). Specifically, we compare the aggregation and photophysical properties of an iodinated squaraine dye and an iodinated squaraine-rotaxane. Even under strongly aggregating conditions, the absorption spectra of both remain relatively sharp. An X-ray crystal structure of the iodinated squaraine dye shows that it adopts perpendicular, end-to-face orientations in the solid state. Singlet oxygen generation efficiency was measured by trapping with 1,3-diphenylisobenzofuran. The triplet state of the rotaxane was characterized using laser flash photolysis. The results of this study suggest that heavily halogenated squaraine-rotaxanes have potential as singlet oxygen photosensitizers for PDT.

Graphical abstract: Singlet oxygen generation using iodinated squaraine and squaraine-rotaxane dyes

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Publication details

The article was received on 07 Nov 2006, accepted on 28 Nov 2006 and first published on 20 Dec 2006


Article type: Paper
DOI: 10.1039/B616224J
Citation: New J. Chem., 2007,31, 677-683
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    Singlet oxygen generation using iodinated squaraine and squaraine-rotaxane dyes

    E. Arunkumar, P. K. Sudeep, P. V. Kamat, B. C. Noll and B. D. Smith, New J. Chem., 2007, 31, 677
    DOI: 10.1039/B616224J

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