LAUSR

The design and synthesis of phthalimide derivatives are important goals for applications in fields like pharmaceutical science and optoelectronics. In the present study, we devised a facile and convenient synthetic pathway (no heat or acid/catalyst needed) to produce phthalimides from a biomass-derived furan by directly introducing an N-carbamate group at the C-2 position of the furan ring via thermal Curtius rearrangement. The electron-donating N-carbamate group increased the energy level of the highest occupied molecular orbital of the furan diene, resulting in a significant increase of the rate of the Diels-Alder reaction with maleimide compared to the conventional furfuryl furan. Interestingly, the Diels-Alder adduct smoothly underwent aromatization (dehydration) to generate the phthalimide motif. We showed that the biomass-derived phthalimides can produce supramolecular gels and act as sensors of basic anions like F- and CN- . The novel synthetic pathway to phthalimide derivatives from a biomass-derived furan could potentially be used to develop novel phthalimide motifs for a variety of applications. This article is protected by copyright. All rights reserved.