Synthesis and structure of 2,6-bis(2-methoxyphenyl)dithiazolo[4,5-b:5′,4′-e]pyridine) as a novel fluorescent sensor: different recognition of transition metal ions and proton

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• 作者：Hossein Reza Darabi^a ; ^{darabi@ccerci.ac.ir" class="auth_mail" title="E-mail the corresponding author} ; ^{r_darabi@yahoo.com" class="auth_mail" title="E-mail the corresponding author} ; Maryam Kargar^a ; ¹ ; Roghayeh Hajipoor^a ; ¹ ; Negar Abouali^a ; ¹ ; Kioumars Aghapoor^a ; ¹ ; Khosrow Jadidi^b ; Behrouz Notash^b ; Hani Sayahi^a ; ¹
• 关键词：Dithiazolopyridine derivative ; Willgerodt&ndash ; Kindler reaction ; Chemosensor
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：20 January 2016
• 年：2016
• 卷：57
• 期：3
• 页码：256-259
• 全文大小：1281 K

文摘

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.