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The Synthesis and Optical Properties of Fluorescent Quinoxalines and of Electrospun Fibers Containing Fluorescent Quinoxaline

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Abstract:

Heterocyclic fluorophores are useful materials in the search for new biologically active compounds and diagnostic methods. We have been interested in the chemistry of nitrogen-containing heterocyclic molecules for many years. Quinoxaline is a representative fluorophore. We have reported on several quinoxalines in recent years. Quinoxaline can easily change its absorption and emission wavelength by oxidation with the proton base in the nitrogen of the quinoxaline ring. In this study, we designed and synthesized several 2,3-distyrylquinoxaline and thieno[3,4-b]quinoxaline derivatives, Each with different electron-donating capabilities. The designed quinoxalines were substituted for the dodecyloxy groups on the benzene ring and stillbene groups were attached by knoevenagel reaction or Hornor-Wadsworth-Emmons (HWE) reaction on the 2,3-positions of the pyrazine ring. They amplified the electron donating capability of the quinoxaline structure. Thus, the weak base property of nitrogen in the heterocyclic ring was increased, especially in a protonic condition. The property in an acidic condition was revealed by fluorescence quenching. However, fluorescent spectral change was observed, especially when the N,N-dimethylamino group was attached to the stillbene group. These properties were also observed in electrospun fibers containing those synthesized compounds. Electrospun fibers contained quinoxaline colorants are expected to have various applications in chemosensors.

Keywords: CHEMICAL SENSOR; FLUORESCENCE; QUINOXALINE

Document Type: Research Article

DOI: https://doi.org/10.1166/jnn.2011.3245

Publication date: 2011-01-01

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  • Journal for Nanoscience and Nanotechnology (JNN) is an international and multidisciplinary peer-reviewed journal with a wide-ranging coverage, consolidating research activities in all areas of nanoscience and nanotechnology into a single and unique reference source. JNN is the first cross-disciplinary journal to publish original full research articles, rapid communications of important new scientific and technological findings, timely state-of-the-art reviews with author's photo and short biography, and current research news encompassing the fundamental and applied research in all disciplines of science, engineering and medicine.
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