Fluorescence control on panchromatic spectra via c-alkylation on arylated quinoxalines.

J Org Chem

Department of Materials Chemistry, Sejong Campus, Korea University, Chung-Nam 339-700, South Korea.

Published: April 2009

AI Article Synopsis

  • A coherent green fluorescence was achieved by modifying 2-position of quinoxalines through butylation, resulting in new quinoxaline derivatives.
  • These derivatives were synthesized by altering the electronic properties of specific positions in the molecule, using various chemical groups such as -H, -OMe, -NPh(2), -NMe(2), and -NMePh.
  • The butylation process transformed an imine group in the pyrazine ring to an amine, changing its electron donor and acceptor characteristics, which led to the observed green fluorescence.

Article Abstract

A coherent green fluorescence was obtained by butylation at the 2-position of panchromatic 2,3-diaryl-5,8-diarylquinoxalines (2) to give corresponding 2-butyl-2,3-diaryl-5,8-diaryl-1H-quinoxalines (3). Full color quinoxaline derivatives (2) were prepared from electronic modification at either the 2,3- or 5,8-positions at the peripheral ArX group or X group (X = -H, -OMe, -NPh(2), -NMe(2), -NMePh) of the quinoxalines. 2-Butylation converted one imine unit of the pyrazine ring to an amine group, which effectively altered the electron donor and acceptor functions to produce a coherent green fluorescence.

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Source
http://dx.doi.org/10.1021/jo9002147DOI Listing

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