AIEE Active Nanoassemblies of Pyrazine Based Organic Photosensitizers as Efficient Metal-Free Supramolecular Photoredox Catalytic Systems

Scientific Reports
Shruti DadwalVandana Bhalla

Abstract

Pyrazine derivatives DIPY, TETPY and CNDIPY have been designed and synthesized which form fluorescent supramolecular assemblies in mixed aqueous media due to their AIEE and ICT characteristics. Among all the derivatives, the assemblies of TETPY and CNDIPY show strong absorption in the visible region with high absorption coefficients, low HOMO-LUMO gap, and high photostability. Further, the supramolecular nanoassemblies of TETPY and CNDIPY show excellent potential to generate reactive oxygen species (ROS) under the visible light irradiation. Owing to their strong absorption in the visible region and ROS generation ability, the supramolecular nanoassemblies of TETPY and CNDIPY act as efficient photoredox catalytic systems for carrying out (a) oxidative amidation of aromatic aldehydes (b) hydroxylation of boronic acid and (c) oxidative homocoupling of benzylamines under mild conditions such as aqueous media, aerial environment, and natural sunlight as a source of irradiation. All the mechanistic investigations suggest the participation of in-situ generated ROS in the organic transformations upon light irradiation.

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Citations

Nov 27, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Mandeep KaurVandana Bhalla
Jul 24, 2020·The Journal of Organic Chemistry·Harnimarta DeolVandana Bhalla

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Methods Mentioned

BETA
amidation
fluorescence studies
transmission electron microscopy
dynamic light scattering
X-ray
cyclic

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