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  • Title: Aggregation-Induced Singlet Oxygen Generation: Functional Fluorophore and Anthrylphenylene Dyad Self-Assemblies.
    Author: Kim S, Zhou Y, Tohnai N, Nakatsuji H, Matsusaki M, Fujitsuka M, Miyata M, Majima T.
    Journal: Chemistry; 2018 Jan 12; 24(3):636-645. PubMed ID: 29105156.
    Abstract:
    The assembly of monomeric building blocks can manifest the display of new properties, including optical, mechanical, and electrochemical functionalities. In this study, we sought to develop a functional fluorophore self-assembly that can generate reactive oxygen species only when aggregated. With an anthrylphenylene (AP) group, negatively charged and neutral fluorescein units form non-fluorescent H-aggregates in aqueous solution because of the weak intermolecular interaction between the anthracene and fluorescein moieties. In stark contrast, a boron dipyrromethene (BODIPY) and AP dyad produces two-color-emissive aggregates through the formation of an intermolecular charge-transfer (CT) complex between the electron-rich anthracene and electron-deficient BODIPY moieties. Furthermore, to our surprise, the BODIPY and AP dyad aggregates generate singlet oxygen (1 O2 ) and photocytotoxicity upon excitation, indicating that the BODIPY-anthracene CT state favors an intersystem crossing process. Based on X-ray crystallographic analysis, the lattice-like molecular packing between the BODIPY and AP moieties was determined to bring about the unprecedented aggregation-induced 1 O2 generation (AISG).
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