Nanophotosensitizing through Space Charge Transfer Assemblies of Pentacenequinone Derivative for 'Metal-free' Photoamidation Reactions

Chem Asian J. 2024 Jan 23:e202300954. doi: 10.1002/asia.202300954. Online ahead of print.ABSTRACTThe present study demonstrates the influence of small portion (20 %) of organic co-solvent (DMSO/THF/ACN/MeOH) in mixed aqueous media (80 % water) in controlling the size, quantum yield and life time of the through space charge transfer assemblies (TSCT) of pentacenequinone derivative (TPy-PCQ-TPy). Among various solvent systems [H2 O : DMSO (8 : 2), H2 O : THF (8 : 2), H2 O : ACN (8 : 2) and H2 O : MeOH (8 : 2)] examined, highly emissive (Φf =12 %) and nano-sized assemblies having long life time (3.11 ns) were formed in H2 O : DMSO (8 : 2) solvent system. The solvent dependent differences in the size and excited state properties of TPy-PCQ-TPy assemblies are reflected in their photosensitizing behaviour in different solvent systems. Backed by excellent photosensitizing properties, TPy-PCQ-TPy assemblies smoothly catalyse the photoamidation reactions between unactivated/activated aldehydes and secondary amine under mild reaction conditions (visible light irradiation, aerial atmosphere, room temperature) in H2 O : DMSO (8 : 2) solvent mixture. The as prepared assemblies of TPy-PCQ-TPy also exhibit high potential to catalyse the oxidation of benzyl alcohols to aromatic aldehydes, thus, generating a possibility to use aromatic alcohols as the starting material in photoamidation reactions. The real time application of TSCT assemblies has also been demonstrated in gram scale transform...
Source: Chemistry, an Asian Journal - Category: Chemistry Authors: Source Type: research