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Pyridine-2-yl Quinoxaline (2-CPQ) Derivative As a Novel Pink Fluorophore: Synthesis, and Chemiluminescence Characteristics

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Abstract

Quinoxaline derivatives are well-known N-heterocycles with pharmacological and fluorescence activities. Almost all quinoxaline derivatives with extensive π-conjugation have been introduced as fluorophores which emit blue and green light. For the first time, we designed and synthesized 6-chloro-2,3 di(Pyridine-2yl) quinoxaline (2-CPQ) as a pink fluorophore in acetonitrile medium by simple route at room temperature whitin 30 min. The synthesized quinoxaline was identified using 1H, 13C NMR, MS, and FT-IR spectroscopy. Our results showed that the iodine-catalyzed method for both oxidation and cyclization during the synthesis of quinoxaline from pyridine 2-carbaldehyde was straightforward, efficient, and clean. All of the mentioned characterization devices confirmed the synthesis of 2-CPQ.

Moreover, we studied the photophysical properties of the synthesized fluorophore in which The UV–Vis absorption spectrum of 2-CPQ in DMF were three peaks at 451, 518 and 556 nm. Based on photophysical properties investigation, 2-CPQ shows good fluorescence with maximum peaks 607 and 653 nm in DMF as solvent (фF = 0.21). Hence, the fluorophore was applied in the peroxyoxalate chemiluminescence system. The reaction of imidazole, H2O2, and bis (2,4,6-trichlorophenyl) oxalate (TCPO) can transfer energy to a 6-chloro-2,3 di(pyridine-2yl) quinoxaline. In this process, dioxetane was synthesized, which chemically initiated the electron exchange luminescence (CIEEL) mechanism and led to pink light emission. We anticipate our synthesized fluorophores 2-CPQ will have great potential applications in imaging and medical markers.

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Acknowledgements

This research was supported by a grant from the research council of Mazandaran University of Medical Sciences, Iran (No. 1161), this work dedicated to a part of Zahra Hashemi's post-doctoral project.

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Authors and Affiliations

  1. Pharmaceutical Sciences Research Center, Department of Medicinal Chemistry, School of Pharmacy, Hemoglobinopathy Institute, Mazandaran University of Medical Sciences, Sari, Iran

    Zahra Hashemi & Mohammad Ali Ebrahimzadeh

  2. Department of Basic Sciences, Sari University of Agricultural Sciences and Natural Resources, P.O.Box 578, Sari, Iran

    Pourya Biparva & Seyed Mohammad Abedirad

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  1. Zahra Hashemi
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  2. Mohammad Ali Ebrahimzadeh
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  3. Pourya Biparva
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  4. Seyed Mohammad Abedirad
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Zahra Hashemi was the first researcher, summarized the synthesis and characterization of 2-CPQ. Mohammad Ali Ebrahimzadeh was the principal investigator and designed the study. Pourya Biparva was the principal investigator and designed the analysis. Data analysis was performed by Seyed Mohammad Abedirad.

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Correspondence to Mohammad Ali Ebrahimzadeh or Pourya Biparva.

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Hashemi, Z., Ebrahimzadeh, M.A., Biparva, P. et al. Pyridine-2-yl Quinoxaline (2-CPQ) Derivative As a Novel Pink Fluorophore: Synthesis, and Chemiluminescence Characteristics. J Fluoresc 32, 723–736 (2022). https://doi.org/10.1007/s10895-022-02890-w

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