title: N-2-aryl-1,2,3-triazoles: a novel class of UV/blue-light-emitting fluorophores with tunable optical properties.
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 (λ(max)) 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, λ(max)=390), which suggested the great potential of this new class of fluorophores in biological and material science research.
authors: C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA.
authors: Wuming
authors: W
authors: Yan
authors: Qiaoyi
authors: Q
authors: Wang
authors: Quan
authors: Q
authors: Lin
authors: Minyong
authors: M
authors: Li
authors: Jeffrey L
authors: JL
authors: Petersen
authors: Xiaodong
authors: X
authors: Shi
mesh_terms: D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D005456:Fluorescent Dyes; D014230:Triazoles