Turning on fluorescent emission from C-alkylation on quinoxaline derivatives

Ho Jin Son; Won Sik Han; Kyung Ryang Wee; Dae Hwan Yoo; Jong Ho Lee; Soon Nam Kwon; Jaejung Ko; Sang Ook Kang

doi:10.1021/ol802287k

Turning on fluorescent emission from C-alkylation on quinoxaline derivatives

Ho Jin Son^*
, Won Sik Han
, Kyung Ryang Wee
, Dae Hwan Yoo
, Jong Ho Lee
, Soon Nam Kwon
, Jaejung Ko
, Sang Ook Kang

^*Corresponding author for this work

Korea University (SEJONG)

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

26 Citations (Scopus)

Abstract

(Figure Presented) 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 (sp³-type) and electron-accepting imine (sp²-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%).

Original language	English
Pages (from-to)	5401-5404
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	23
DOIs	https://doi.org/10.1021/ol802287k
Publication status	Published - 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol802287k

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@article{16c525ea09d345e6ba568612712b9315,

title = "Turning on fluorescent emission from C-alkylation on quinoxaline derivatives",

abstract = "(Figure Presented) 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 (sp3-type) and electron-accepting imine (sp2-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\%).",

author = "Son, \{Ho Jin\} and Han, \{Won Sik\} and Wee, \{Kyung Ryang\} and Yoo, \{Dae Hwan\} and Lee, \{Jong Ho\} and Kwon, \{Soon Nam\} and Jaejung Ko and Kang, \{Sang Ook\}",

year = "2008",

doi = "10.1021/ol802287k",

language = "English",

volume = "10",

pages = "5401--5404",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - Turning on fluorescent emission from C-alkylation on quinoxaline derivatives

AU - Son, Ho Jin

AU - Han, Won Sik

AU - Wee, Kyung Ryang

AU - Yoo, Dae Hwan

AU - Lee, Jong Ho

AU - Kwon, Soon Nam

AU - Ko, Jaejung

AU - Kang, Sang Ook

PY - 2008

Y1 - 2008

N2 - (Figure Presented) 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 (sp3-type) and electron-accepting imine (sp2-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%).

AB - (Figure Presented) 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 (sp3-type) and electron-accepting imine (sp2-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%).

UR - https://www.scopus.com/pages/publications/61349087331

U2 - 10.1021/ol802287k

DO - 10.1021/ol802287k

M3 - Article

AN - SCOPUS:61349087331

SN - 1523-7060

VL - 10

SP - 5401

EP - 5404

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Turning on fluorescent emission from C-alkylation on quinoxaline derivatives

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