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Turning on Fluorescent Emission from C-Alkylation on Quinoxaline Derivatives

Authors
Son, Ho-JinHan, Won-SikWee, Kyung-RyangYoo, Dae-HwanLee, Jong-HoKwon, Soon-NamKo, JaejungKang, Sang Ook
Issue Date
4-12월-2008
Publisher
AMER CHEMICAL SOC
Citation
ORGANIC LETTERS, v.10, no.23, pp.5401 - 5404
Indexed
SCIE
SCOPUS
Journal Title
ORGANIC LETTERS
Volume
10
Number
23
Start Page
5401
End Page
5404
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/122241
DOI
10.1021/ol802287k
ISSN
1523-7060
Abstract
Reduction on imine moiety (C=N) of quinoxalines by alkyl-/aryllithiums led to a geometrical change on the quinoxaline ring, thereby perturbing the electronic structure to turn on fluorescence emission. Such a structural change resulted in interrupted cyclic-ring systems with electron-donating amine (Sp(3)-type) and electron-accepting imine (Sp(2)-type) units bridged by a phenylene unit. Through either alkylation or arylation, a highly polarized electron donor-electron acceptor bipolar system was established in a single molecule with dramatically enhanced PL efficiency (up to 60%).
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