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A Highly Stable Organic Luminescent Diradical

Alim Abdurahman, Jingmin Wang, Yihan Zhao, Ping Li, Li Shen, Qiming Peng

2023Angewandte Chemie International Edition86 citationsDOIOpen Access PDF

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.

Topics & Concepts

DiradicalLuminescenceSinglet fissionSinglet stateOpen shellDelocalized electronPhotochemistryExcited stateTriplet stateChemistrySteric effectsChemical physicsGround stateMaterials scienceAtomic physicsOrganic chemistryOptoelectronicsPhysicsMagnetism in coordination complexesOrganic and Molecular Conductors ResearchSynthesis and Properties of Aromatic Compounds
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