A Highly Stable Organic Luminescent Diradical

Angew Chem Int Ed Engl. 2023 Apr 3;62(15):e202300772. doi: 10.1002/anie.202300772. Epub 2023 Mar 2.

Abstract

It is very challenging to obtain stable room-temperature luminescent open-shell singlet diradicals. Herein we report the first stable Müller's hydrocarbon TTM-PhTTM with luminescent properties. Variable-temperature electron paramagnetic resonance spectroscopy measurements and theoretical calculations show that TTM-PhTTM has an open-shell singlet ground state with a diradical character of 90 %. Because of a small singlet-triplet energy gap, the open-shell singlet ground state can be thermally excited to a triplet state. TTM-PhTTM shows room-temperature deep-red emission in various solutions. Unusually high stability of TTM-PhTTM was also observed owing to effective steric hindrance and spin delocalization. Our results are beneficial to the rational design and discovery of more stable luminescent diradical materials.

Keywords: Luminescent Diradical; Müller's Hydrocarbon; Open-Shell Singlet Diradicals; Radical Stability.