Bis(4-hydroxythiazoles): Novel Functional and Switchable Fluorophores

Abstract

A series of 2,2′- and 5,5′-bis(4-hydroxythiazoles) was synthesized according to Hantzsch synthesis. Both phenols and their corresponding anions display a strong fluorescence in the visible spectrum, whereas the emission is shifted bathochromically upon deprotonation. This easy switch makes them suitable for widespread applications, mainly in analysis and supramolecular chemistry. Due to their 1,4-diazadiene substructure, the 2,2′-bithiazoles possess prerequisites for the complexation of metals, however, instead of a copper complex, a dimer which constitutes the 5,5′-C-C coupled product was isolated. In addition, tris(thiazoles) could be constructed.

Key words

heterocycles - chromophores - bifunctional compounds - condensation - thiazole

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Supporting Information Available: Crystallographic data deposited at the Cambridge Crystallographic Data Centre under CCDC-813194 for 4a, and CCDC-813195 for 16 contain the supplementary crystallographic data excluding structure factors; this data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html, or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; or [e-mail].