Chalcogen Effect of Atom Substitution on the Properties of Tris(2,4,6-trichlorophenyl)methyl(TTM) Radical

doi:10.1007/s40242-023-3008-2

Chemical Research in Chinese Universities ›› 2023, Vol. 39 ›› Issue (2): 197-201.doi: 10.1007/s40242-023-3008-2

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Chalcogen Effect of Atom Substitution on the Properties of Tris(2,4,6-trichlorophenyl)methyl(TTM) Radical

YANG Yiming, QIU Lili, SHI Xueliang

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. China

Received:2023-01-11 Online:2023-04-01 Published:2023-03-16
Contact: SHI Xueliang E-mail:xlshi@chem.ecnu.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (No.52003081) and the Shanghai Natural Science Foundation, China (No.22ZR1420600).

Abstract

Abstract: Luminescent open-shell organic radicals have recently been regarded as one of the most potential materials in organic light-emitting diodes(OLEDs). Herein, we have synthesized two new organic radicals, namely tris{4-[4-(tert-butyl)phenoxy]-2,6- dichlorophenyl}methane radical(TTM-O) and tris(4-{[4-(tert-butyl)- phenyl]thio}-2,6-dichlorophenyl)methane radical(TTM-S), by the substitution of chalcogen atom elements at the para position of conventional tris(2,4,6-trichlorophenyl)methyl(TTM) radical moiety. Interestingly, both TTM-O and TTM-S exhibited significantly enhanced photostability compared with the unsubstituted TTM radical parent. Moreover, the chalcogen atom also had a crucial impact on the photoluminescence quantum yield(PLQY) of the radicals, i.e., the PLQY of TTM-S was greatly enhanced compared to TTM radical while TTM-O was nearly non-emissive. Particularly, TTM-S showed intense PLQY of 37.54% and 185-fold longer photostability than that in cyclohexane solution of TTM.

Key words: Luminescent organic radical, Chalcogen atom effect, Photoluminescence quantum yield(PLQY), Photostability, Electron paramagnetic resonance(EPR)

YANG Yiming, QIU Lili, SHI Xueliang. Chalcogen Effect of Atom Substitution on the Properties of Tris(2,4,6-trichlorophenyl)methyl(TTM) Radical[J]. Chemical Research in Chinese Universities, 2023, 39(2): 197-201.

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Chalcogen Effect of Atom Substitution on the Properties of Tris(2,4,6-trichlorophenyl)methyl(TTM) Radical

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