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Published on: September 12, 2014
Light-Driven Photoconversion of Squaramides with Implications in Anion Transport
Manel Vega1, Luis Martínez-Crespo1, Miguel Barceló-Oliver1
1Department of Chemistry, Universitat de les Illes Balears, Palma 07122, Spain.
Abstract:
Simple, clean and fast photoconversion of aniline-derived squaramides was achieved by flashlight illumination. UV irradiation enabled the photochemical squaramide ring-opening to generate 1,2-bisketenes, which DMSO trapped as the nucleophilic oxidant. The only photoproducts isolated were 3,4-arylamino maleic anhydrides, which present conformational preferences very different from those of their parent squaramides. Similar photoconversion was achieved in MeOH. The UV-mediated time-dependent anion transport inhibition was demonstrated, establishing a new approach for modulating the transport abilities of AD-squaramides.
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