Construction of a novel tetraphenylethylene-based supramolecular dimer for improving the generation of reactive oxygen species and photocatalytic performance

Abstract

Using supramolecular strategies to improve the generation of reactive oxygen species is a practical and environmentally friendly method, but it is also a difficult undertaking. In this study, we created and produced a vinylpyridine-modified tetraphenylethylene derivative TPE-Py-I, which has excellent solubility in water and has the ability to construct supramolecular dimers (2TPE-Py-I@CB[8]) in an aqueous solution through host-guest interaction with cucurbit[8]uril (CB[8]). The supramolecular dimer demonstrated a remarkable aggregation-induced emission response, with the fluorescence progressively intensifying upon the introduction of CB[8]. Meanwhile, the formation of supramolecular dimer also greatly improved the intersystem crossing effect of the molecular assembly system, so that the generation ability of reactive oxygen species including singlet oxygen (¹O₂) and superoxide anion radical (O₂^•-) were enhanced, which provided a basis for its application as an excellent supramolecular photosensitizer in photocatalytic organic reactions. To our delight, 2TPE-Py-I@CB[8] exhibits excellent photocatalytic properties, making it suitable for both phosphine photooxidation and cross-dehydrogenative coupling reactions. This work provides a non-covalent strategy for the development of supramolecular dimer photosensitizers and broadens its application in the field of photocatalytic organic conversion.

Keywords

Supramolecular dimer / reactive oxygen species / photocatalyst / photooxidation reaction

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