A single isomer rotary switch demonstrating anti-Kasha behaviour: Does acidity function matter?

Phys Chem Chem Phys. 2021 Jun 28;23(24):13760-13767. doi: 10.1039/d1cp01378e. Epub 2021 Jun 15.

Abstract

A novel rotary switch, overcoming the disadvantages of hydrazone based switches with competitive proton acceptor sub-rotors, has been designed. The new compound contains a pyridyl ring and a COOH group as sub-rotors, which provides engagement of the pyridyl nitrogen atom and leads to the existence of a single isomer in the ground state. The availability of acidic functionality in the rotor creates conditions for excited state intramolecular proton transfer (ESIPT), which exhibits anti-Kasha behavior.