C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA.
Chemistry. 2011 Apr 26;17(18):5011-8. doi: 10.1002/chem.201002937. Epub 2011 Mar 22.
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.
N-2-芳基-1,2,3-三唑衍生物（NATs）被开发为一类新型的紫外/蓝光发射荧光团。尽管 N-1-芳基-1,2,3-三唑和 N-2-芳基-1,2,3-三唑在 330nm 激发下都能产生强烈的光吸收，但只有 N-2-类似物在各种溶剂中显示出强的紫外/蓝光荧光发射，效率高（量子产率 Φ 在 0.3-0.5 左右）。观察到显著的取代基效应，允许通过发射（λ(max))从 350-400nm 和斯托克斯位移从 38-93nm 来调节光学性质。计算研究以及 X 射线晶体结构表明，N-2 位上三唑环和芳基之间的有效共轭对其具有重要意义。提出了平面分子内电荷转移（PICT）机制，溶剂效应研究支持了这一机制。简单的衍生化得到了 NAT 修饰的赖氨酸和强的紫外/蓝光发射双 NAT（Φ=0.76，λ(max)=390），这表明这种新型荧光团在生物和材料科学研究中有很大的潜力。
