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Radical and Diradical Formation in Naphthalene Diimides through Simple Chemical Oxidation
Author(s) -
Lee Sangsu,
Miao Fang,
Phan Hoa,
Herng Tun Seng,
Ding Jun,
Wu Jishan,
Kim Dongho
Publication year - 2017
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201700015
Subject(s) - diradical , electron paramagnetic resonance , photochemistry , chemistry , singlet state , excited state , radical , ground state , radical ion , nuclear magnetic resonance , organic chemistry , atomic physics , physics , ion
Abstract We successfully synthesized, for the first time, a naphthalene diimide (NDI) radical and diradical by simple chemical oxidation using lead(IV) dioxide. The formation of the (di)radical is confirmed by UV/Vis/NIR absorption, 1 H NMR, and electron paramagnetic resonance (EPR) measurements. In particular, temperature‐dependent EPR, SQUID (superconducting quantum interference device) measurements, and quantum calculations demonstrated that the generated NDI diradical has a singlet diradical character of y= 0.69 in the ground state. Subsequent characterization of this (di)radical revealed its stabilities, large two‐photon absorption cross‐section, and short excited‐state lifetime.