Radical and Diradical Formation in Naphthalene Diimides through Simple Chemical Oxidation

Sangsu Lee; Fang Miao; Hoa Phan; Tun Seng Herng; Jun Ding; Jishan Wu; Dongho Kim

doi:10.1002/cphc.201700015

Radical and Diradical Formation in Naphthalene Diimides through Simple Chemical Oxidation

Sangsu Lee, Fang Miao, Hoa Phan, Tun Seng Herng, Jun Ding, Jishan Wu, Dongho Kim

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

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, ¹H 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.

Original language	English
Pages (from-to)	591-595
Number of pages	5
Journal	ChemPhysChem
Volume	18
Issue number	6
DOIs	https://doi.org/10.1002/cphc.201700015
Publication status	Published - 2017 Mar 17

Bibliographical note

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Atomic and Molecular Physics, and Optics
Physical and Theoretical Chemistry

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10.1002/cphc.201700015

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title = "Radical and Diradical Formation in Naphthalene Diimides through Simple Chemical Oxidation",

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, 1H 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.",

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T1 - Radical and Diradical Formation in Naphthalene Diimides through Simple Chemical Oxidation

AU - Lee, Sangsu

AU - Miao, Fang

AU - Phan, Hoa

AU - Herng, Tun Seng

AU - Ding, Jun

AU - Wu, Jishan

AU - Kim, Dongho

PY - 2017/3/17

Y1 - 2017/3/17

N2 - 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, 1H 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.

AB - 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, 1H 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.

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Radical and Diradical Formation in Naphthalene Diimides through Simple Chemical Oxidation

Abstract

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