Classical heterocycles with surprising properties: the 4-hydroxy-1,3-thiazoles

Single‐Molecular White‐Light Emitters and Their Potential WOLED Applications

“…Copyright 2017, The Royal Society of Chemistry. e) Reproduced with permission . Copyright 2011, Elsevier.…”

“…In the absence of intramolecular hydrogen bonding, the transformation of enol to keto forms can be achieved by the alkali‐assistant deprotonation. For instance, Beckert and co‐workers reported DMSO‐assisted deprotonation of 4‐hydroxythiazole derivative 5‐phenyl‐2‐(pyridin‐2‐yl)thiazol‐4‐ol ( 86 ), which equilibrates the coexistence of emissions from E* and K* resulting in a white‐light emission (Figure e) …”

Synthesis and applications of 2,4-disubstituted thiazole derivatives as small molecule modulators of cellular development

“…18 The lower energy of the aromatic 4-hydroxythiazole structure, as well as the presence of an aromatic substituent at the 2-position, is likely to account for the preferred enol form in this case. 19 Alkylation of the mixture of 5a and 5b would be expected 85 to 'lock' the product in the aromatic form; indeed, after reaction with 2-bromoethyl ethyl ether to give 6, loss of signals associated with the keto-tautomer was observed by 1 H NM R analysis of the product. Following a basic hydrolysis, alkoxythiazole 1 was obtained in 56% yield after recrystallisation.…”

Solution-and solid-state emitters with large Stokes shifts combining pyrene and 4-hydroxythiazole fluorophores

“…More important second components were found for 3a,g (9)(10)(11)(12)(13)(14)(15)(16)%. In all cases the lifetime of the sole (main) component was relatively short (~0.6-1 ns).…”