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PET-based bisBODIPY photosensitizers for highly efficient excited triplet state and singlet oxygen generation: tuning photosensitizing ability by dihedral angles

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Abstract

Herein, four covalent BODIPY heterodimers that differ by dihedral angles were shown to be highly efficient excited triplet state (T1) photosensitizers (PSs) for singlet oxygen formation with a quantum yield (ΦΔ) of up to 0.94 as compared to their respective monomers, which had only negligible ΦΔ of ca. 0.060. More interestingly, these PSs generate T1 via charge recombination mechanism rather than traditional inter-system crossing. The photosensitizing ability of dimers is easily tuned by either the dihedral angle (between the two linked BODIPYs) or solvent polarity. Laser flash photolysis, time-resolved and steady state fluorescence, quantum chemical calculation, as well as thermodynamic analysis were employed to study the associated photophysical process to reveal the T1 formation mechanism: photo-induced electron transfer (PET) followed by charge recombination. Due to its heavy-atom-free nature, polarity selectivity, high efficiency, and easy tunability, this PET-based PS and its mechanism are very useful in developing new PS for photodynamic therapy of tumors, photobiology, and organic photochemistry.

Graphical abstract: PET-based bisBODIPY photosensitizers for highly efficient excited triplet state and singlet oxygen generation: tuning photosensitizing ability by dihedral angles

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Publication details

The article was received on 22 Apr 2017, accepted on 20 Aug 2017 and first published on 21 Aug 2017


Article type: Paper
DOI: 10.1039/C7CP02645E
Citation: Phys. Chem. Chem. Phys., 2017, Advance Article
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    PET-based bisBODIPY photosensitizers for highly efficient excited triplet state and singlet oxygen generation: tuning photosensitizing ability by dihedral angles

    X. Zhang, X. Yang and B. Xu, Phys. Chem. Chem. Phys., 2017, Advance Article , DOI: 10.1039/C7CP02645E

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