Exploiting radical-pair intersystem crossing for maximizing singlet oxygen quantum yields in pure organic fluorescent photosensitizers.

Chemical Science
Xuanhang WangWenjing Tian

Abstract

Fluorescent photosensitizers (PSs) often encounter low singlet oxygen (1O2) quantum yields and fluorescence quenching in the aggregated state, mainly involving the intersystem crossing process. Herein, we successfully realize maximizing 1O2 quantum yields of fluorescent PSs through promoting radical-pair intersystem crossing (RP-ISC), which serves as a molecular symmetry-controlling strategy of donor-acceptor (D-A) motifs. The symmetric quadrupolar A-D-A molecule PTP exhibits an excellent 1O2 quantum yield of 97.0% with bright near-infrared fluorescence in the aggregated state. Theoretical and ultrafast spectroscopic studies suggested that the RP-ISC mechanism dominated the formation of the triplet for PTP, where effective charge separation and an ultralow singlet-triplet energy gap (0.01 eV) enhanced the ISC process to maximize 1O2 generation. Furthermore, in vitro and in vivo experiments demonstrated the dual function of PTP as a fluorescent imaging agent and an anti-cancer therapeutic, with promising potential applications in both diagnosis and theranostics.

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Methods Mentioned

BETA
fluorescence imaging
dynamic light scattering
electron exchange

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