Triazolopyridines. Part 28. The ring–chain isomerization strategy: triazolopyridine- and triazoloquinoline–pyridine based fluorescence ligands

• Published in: Tetrahedron 2012-05, Vol.68 (19), p.3701-3707
• Main Authors: Ballesteros-Garrido, Rafael, Delgado-Pinar, Estefanía, Abarca, Belén, Ballesteros, Rafael, Leroux, Frédéric R., Colobert, Françoise, Zaragozá, Ramón J., García-España, Enrique
• Format: Article
• Language: English
• Subjects: Cations; Chemical Sciences; Chemistry; Condensed benzenic and aromatic compounds; Constants; Cyanide sensing; Derivatives; Exact sciences and technology; Fluorescence; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Isomerization; Naphthalene; Nitrite sensing; Organic chemistry; Preparations and properties; Quinolines; Triazolopyridines; Zinc; Zinc(II) sensing
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2012.03.029

The ring–chain isomerization of [1,2,3]triazolo[1,5-a]pyridines or [1,2,3]triazolo[1,5-a] quinolines has been efficiently employed as a tool to provide tridentate fluorescent structures. Based on these scaffolds, a new family of highly fluorescent compounds has been synthesized and evaluated for the recognition of zinc or copper cations. In addition, the 1:1 Zn+2-L complex of a naphthalene triazolopyridine–pyridine derivative revealed high efficiency as sensor for anions providing large binding constants for nitrite and cyanide. [Display omitted]