Tetrahedron Letters ( IF 1.5 ) Pub Date : 2015-12-02 , DOI: 10.1016/j.tetlet.2015.11.055 Hossein Reza Darabi , Maryam Kargar , Roghayeh Hajipoor , Negar Abouali , Kioumars Aghapoor , Khosrow Jadidi , Behrouz Notash , Hani Sayahi
The fluorophore 2,6-bis(2-methoxyphenyl)dithiazolo[4,5-b:5′,4′-e]pyridine) 3, with a planar structure, was synthesized using a one-pot Willgerodt–Kindler reaction which is potentially applicable to various dithiazolopyridines. The basic photophysical characteristics were investigated in organic solvents of different polarity. Chemosensor 3 exhibits a ‘turn-off’ response toward Cu2+ and Fe3+ ions, as well as a new emission wavelength-ratiometric response to H+ ions, illustrating a different recognition manner. From the binding constant calculations of 3 with Cu2+, increased sensitivity for the fluorescence method over that of the UV–vis method was found, while both methods showed similar sensitivity for binding of 3 with H+. On the other hand, the different behavior in the complexes of 3·H+ and 3·Cu2+ under cyclic voltammetric analysis was observed. These findings suggest that compound 3 may have potential as a sensor for water pollution by Cu2+ and Fe3+ ions as well as protons.
中文翻译:
作为新型荧光传感器的2,6-双(2-甲氧基苯基)二噻唑并[4,5- b:5',4'- e ]吡啶)的合成与结构:对过渡金属离子和质子的不同认识
使用一锅Willgerodt-Kindler反应合成具有平面结构的2,6-双(2-甲氧基苯基)二噻唑并[4,5- b:5',4'- e ]吡啶)3荧光团。可能适用于各种二噻唑并吡啶。在不同极性的有机溶剂中研究了基本的光物理特性。化学传感器3表现出对Cu 2+和Fe 3+离子的“关闭”响应,以及对H +离子的新发射波长比测量响应,说明了一种不同的识别方式。从3与Cu 2+的结合常数计算,发现荧光方法的灵敏度比UV-vis方法的灵敏度提高,而两种方法对3与H +的结合均显示出相似的灵敏度。另一方面,在循环伏安法分析下观察到了3 ·H +和3 ·Cu 2+的配合物的不同行为。这些发现表明,化合物3可能具有被Cu 2+和Fe 3+离子以及质子污染水的传感器的潜力。