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Oxazoline as acceptor moiety for excited-state intramolecular proton transfer

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Abstract Excited state intramolecular proton transfer (ESIPT) is a widespread phenomenon that has been exploited in several analytical and technological applications. Here we describe the synthesis of two ESIPT-active halogen-substituted… Click to show full abstract

Abstract Excited state intramolecular proton transfer (ESIPT) is a widespread phenomenon that has been exploited in several analytical and technological applications. Here we describe the synthesis of two ESIPT-active halogen-substituted naphthol-oxazolines that can be conveniently functionalized to develop tailored sensors, and a bis-oxazoline that showcases the potential of oxazolines to undergo double ESIPT. The photophysical properties of these compounds in solution were investigated using polar aprotic solvents and the results were rationalized using DFT/TD-DFT calculations.

Keywords: state intramolecular; excited state; proton transfer; intramolecular proton

Journal Title: Tetrahedron
Year Published: 2018

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