Radical and Diradical Formation in Naphthalene Diimides through Simple Chemical Oxidation

被引：21
作者：
Lee, Sangsu [1 ]
Miao, Fang [2 ]
Phan, Hoa [2 ]
Herng, Tun Seng [3 ]
Ding, Jun [3 ]
Wu, Jishan [2 ]
Kim, Dongho [1 ]
机构：
[1] Yonsei Univ, Dept Chem & Spect, Lab Funct Elect Syst, Seoul 03722, South Korea
[2] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore
[3] Natl Univ Singapore, Dept Mat Sci & Engn, Singapore 119260, Singapore
来源：
CHEMPHYSCHEM | 2017年 / 18卷 / 06期
基金：
新加坡国家研究基金会;
关键词：
naphthalene diimide; oxidation; radicals; sextet rule; singlet diradicals; BIRADICAL CHARACTERS; 2-PHOTON ABSORPTION; PHYSICAL-PROPERTIES; KEKULE STRUCTURES; GROUND-STATE; CHAIN-LENGTH; SINGLET; PERYLENE; HYDROCARBON; REACTIVITY;
D O I：
10.1002/cphc.201700015
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
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, (HNMR)-H-1, 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.
引用
收藏
页码：591 / 595
页数：5
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