Saleem Muhammad, Lee Ki Hwan
Department of Chemistry, Kongju National University, Gongju, Chungnam, 314-701, Republic of Korea.
J Fluoresc. 2015 Mar;25(2):217-26. doi: 10.1007/s10895-015-1505-5. Epub 2015 Jan 18.
This paper concerns the design, synthesis, structural characterization, thermal stability evaluation and fluorescence properties of novel triazolothiadiazole derivatives. The target compounds 6a-e were synthesized by condensing 4-amino-3-(4-methoxybenzyl)-1H-1,2,4-triazole-5 (4H)-thione (5) with biphenyl, naphthyl, p-terphenyl, pyrenyl and ferrocenyl carboxylic acid in the presence of phosphorous oxychloride. The structures of newly synthesized compounds were characterized by IR, (1)H NMR and (13)C NMR analysis. The photophysical properties of synthesized compounds were measured in a variety of organic solvents of variable polarities. Spectral properties of the compounds were highly dependent on the nature of the substituent and coupling components attached to the triazolothiadiazole skeleton as well as slightly affected by the solvent polarities. Correlation of the absorption spectra and fluorescence emission response of 6a-e with the substituent revealed that the fluorescent properties can easily be tuned by varying conjugation length of side coupled groups. The newly synthesized derivatives represent a new type of fluorescent materials with efficient visible absorption and surpassing brightness which could be a promising candidate for bioimaging, photonic applications, organic light emitting diodes and dye sensitized solar cells.
本文涉及新型三唑并噻二唑衍生物的设计、合成、结构表征、热稳定性评估及荧光性质。目标化合物6a - e是通过在三氯氧磷存在下，使4 - 氨基 - 3 - (4 - 甲氧基苄基)-1H - 1,2,4 - 三唑 - 5(4H)-硫酮(5)与联苯、萘基、对三联苯、芘基和二茂铁基羧酸缩合而合成的。通过红外光谱、¹H核磁共振和¹³C核磁共振分析对新合成化合物的结构进行了表征。在多种极性不同的有机溶剂中测定了合成化合物的光物理性质。化合物的光谱性质高度依赖于连接在三唑并噻二唑骨架上的取代基和偶联组分的性质，同时也受到溶剂极性的轻微影响。6a - e的吸收光谱和荧光发射响应与取代基的相关性表明，通过改变侧链偶联基团的共轭长度可以很容易地调节荧光性质。新合成的衍生物代表了一类新型的荧光材料，具有高效的可见光吸收和卓越的亮度，有望成为生物成像、光子应用、有机发光二极管和染料敏化太阳能电池的候选材料。
