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N-2-Aryl-1,2,3-triazoles: A Novel Class of UV/Blue-Light-Emitting Fluorophores with Tunable Optical Properties

Authors

  • Wuming Yan,

    1. C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA), Fax: (+1) 304-293-4904
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  • Qiaoyi Wang,

    1. C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA), Fax: (+1) 304-293-4904
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  • Prof. Dr. Quan Lin,

    1. State Key Lab of Supramolecular Structure and Materials, Jilin University, Changchun, Jilin, 130012 (P.R. China)
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  • Prof. Dr. Minyong Li,

    1. Department of Medicinal Chemistry, School of Pharmacy, Shandong University, Jinan, Shandong, 250012 (P.R. China)
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  • Prof. Dr. Jeffrey L. Petersen,

    1. C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA), Fax: (+1) 304-293-4904
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  • Prof. Dr. Xiaodong Shi

    Corresponding author
    1. C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA), Fax: (+1) 304-293-4904
    • C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA), Fax: (+1) 304-293-4904
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Abstract

The N-2-aryl-1,2,3-triazole derivatives (NATs) were developed as a new class of UV/blue-light-emitting fluorophores. Though both N-1-aryl-1,2,3-triazoles and N-2-aryl-1,2,3-triazoles gave strong photo absorption under excitation at 330 nm, only the N-2-analogous showed strong fluorescence emission in the UV/blue range with high efficiency in various solvents (quantum yield Φ around 0.3–0.5). Significant substituted group effects were observed, allowing tunable optical properties with emission (λmax) from 350–400 nm and Stokes shift from 38–93 nm. The computational studies along with X-ray crystal structures indicated the significance of the effective conjugation between triazole ring and aryl groups on the N-2 position. The planar intramolecular charge transfer (PICT) mechanism was proposed, which was supported by solvent effect studies. Simple derivatizations gave NAT-modified lysine and strong UV/blue emitting bis-NAT (Φ=0.76, λmax=390), which suggested the great potential of this new class of fluorophores in biological and material science research.

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