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Structure-Property Relationships of Near-Infrared Cyanine Dyes: Chalcogen-Driven Singlet Oxygen Generation with High
Shufan Yang1,2, Ewan Forsyth3, Wuyang Lin4
1School of Chemistry, University of Edinburgh, David Brewster Road, EH9 3FJ Edinburgh, U.K.
Abstract:
We report the design, synthesis, and optical characterisations of eight novel near-infrared (NIR) cyanine dyes incorporating different chalcogens (O, S, and Se). These dyes exhibited excellent deep-NIR absorption (λmax = 767-833 nm) and emission (λmax = 784-859 nm) profiles. TDDFT calculations matched well the experimental trends and data. All compounds exhibited high extinction coefficients (178,000-267,000 cm-1 M-1) and good fluorescence quantum yields, resulting in high overall brightnesses. Remarkably, the selenium-containing dyes featuring terminal indole and benzoindole-type units exhibited impressive singlet oxygen quantum yields of around 13%, a standout performance in the deep-NIR region. These values are particularly promising and highlights the potential of these dyes for deep-NIR imaging and photodynamic applications.
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