Issue 3, 2020

A zinc-responsive fluorophore based on 5′-(p-hydroxyphenyl)-pyridylthiazole

Abstract

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 (ΦPL) 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.

Graphical abstract: A zinc-responsive fluorophore based on 5′-(p-hydroxyphenyl)-pyridylthiazole

Supplementary files

Article information

Article type
Research Article
Submitted
23 Dit 2019
Accepted
18 Qun 2020
First published
20 Qun 2020

Mater. Chem. Front., 2020,4, 899-904

Author version available

A zinc-responsive fluorophore based on 5′-(p-hydroxyphenyl)-pyridylthiazole

Y. Watanabe, W. Sungnoi, A. O. Sartorio, M. Zeller and A. Wei, Mater. Chem. Front., 2020, 4, 899 DOI: 10.1039/C9QM00648F

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