A zinc-responsive fluorophore based on 5′-(p-hydroxyphenyl)-pyridylthiazole,Materials Chemistry Frontiers

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A zinc-responsive fluorophore based on 5′-(p-hydroxyphenyl)-pyridylthiazole
Materials Chemistry Frontiers ( IF 6.0 ) Pub Date : 2020/01/20 , DOI: 10.1039/c9qm00648f
Yuichiro Watanabe _{1,

2,

3,

4} , Wanna Sungnoi _{1,

2,

3,

4} , Andrew O. Sartorio _{2,

3,

4,

5} , Matthias Zeller _{1,

2,

3,

4} , Alexander Wei _{1,

2,

3,

4,

6}

Affiliation

The synthesis and photophysical properties of an ion-sensitive fluorescent compound are described, featuring 5′-(p-hydroxyphenyl)pyridylthiazole (HPPT) as a highly emissive fluorophore. Density functional theory (DFT) calculations indicate that HPPT is capable of intramolecular charge transfer (ICT), with further polarization upon complexation with Zn(II). A 4′-picolyloxy–HPPT derivative was prepared and determined to form a 1 : 1 complex with Zn(NO₃)₂ in acetonitrile, with a Stokes shift of 137 nm (6323 cm⁻¹) and a 67 nm bathochromic shift in emission relative to the neutral ligand, and a fluorescence quantum yield (Φ_PL) of 92%. An X-ray crystal structure of the HPPT–Zn(II) complex confirmed a tridentate structure with a seven-membered chelate ring, and the picolyloxy unit rotated out of plane.

中文翻译：

基于5'-（对羟基苯基）-吡啶基噻唑的锌响应性荧光团

描述了一种离子敏感性荧光化合物的合成和光物理性质，其特征在于5'-（对羟基苯基）吡啶基噻唑（HPPT）作为高发射荧光团。密度泛函理论（DFT）计算表明，HPPT能够进行分子内电荷转移（ICT），并且在与Zn（II）络合时会进一步极化。制备了4'-picolyloxy–HPPT衍生物，并确定其与乙腈中的Zn（NO ₃）₂形成1：1配合物，斯托克斯位移为137 nm（6323 cm ^-1），发射红移为67 nm。相对于中性配体和荧光量子产率（Φ _PL）的92％。HPPT-Zn（II）配合物的X射线晶体结构证实了具有七元螯合环的三齿结构，并且吡啶甲酰氧基单元旋转出平面。

更新日期：2020-03-05

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