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The Effect of Torsional Motion on Multiexciton Formation through Intramolecular Singlet Fission in Ferrocene‐Bridged Pentacene Dimers

Ryo Hayasaka, Hayato Sakai, Masaaki Fuki, T. Okamoto, Ramsha Khan, Masahiro Higashi, Nikolai V. Tkachenko, Yasuhiro Kobori, Taku Hasobe

2024Angewandte Chemie International Edition14 citationsDOIOpen Access PDF

Abstract

Abstract A series of ferrocene(Fc)‐bridged pentacene(Pc)‐dimers [Fc−Ph(2, n )−(Pc) 2 : n =number of phenylene spacers] were synthesized to examine the tortional motion effect of Fc‐terminated phenylene linkers on strongly coupled quintet multiexciton ( 5 TT) formation through intramolecular singlet fission (ISF). Fc−Ph(2,4)−(Pc) 2 has a relatively small electronic coupling and large conformational flexibility according to spectroscopic and theoretical analyses. Fc−Ph(2,4)−(Pc) 2 exhibits a high‐yield 5 TT together with quantitative singlet TT ( 1 TT) generation through ISF. This demonstrates a much more efficient ISF than those of other less flexible Pc dimers. The activation entropy in 1 TT spin conversion of Fc−Ph(2,4)−(Pc) 2 is larger than those of the other systems due to the larger conformational flexibility associated with the torsional motion of the linkers. The torsional motion of linkers in 1 TT is attributable to weakened metal‐ligand bonding in the Fc due to hybridization of the hole level of Pc to Fc in 1 TT unpaired orbitals.

Topics & Concepts

Intramolecular forceChemistryFerrocenePentaceneCrystallographyPhenyleneSinglet stateDimerPhotochemistryLigand (biochemistry)StereochemistryPhysical chemistryExcited stateReceptorOrganic chemistryPhysicsElectrochemistryNuclear physicsPolymerBiochemistryThin-film transistorElectrodeMolecular Junctions and NanostructuresElectron Spin Resonance StudiesMagnetism in coordination complexes