Université de Fribourg

A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols

Hristova, S. ; Deneva, Vera V. ; Pittelkow, M. ; Crochet, Aurélien ; Kamounah, Fadhil S. ; Fromm, Katharina M. ; Hansen, P. E. ; Antonov, Liudmil

In: Dyes and Pigments, 2018, vol. 156, p. 91-99

A series of aryl azo derivatives of naphthols (1–3) were studied by means of UV–Vis and NMR spectroscopy in different solvents as well as by quantum chemical calculations and X-ray analysis. Previous studies have shown that Sudan I (1) exists as a tautomeric mixture. The effect of the solvents is minimized by the existing intramolecular hydrogen bond. Therefore, the influence on the...

Université de Fribourg

Tautocrowns: a concept for a sensing molecule with an active side-arm

Antonov, Liudmil ; Kurteva, Vanya B. ; Simeonov, Svilen P. ; Deneva, Vera V. ; Crochet, Aurélien ; Fromm, Katharina M.

In: Tetrahedron, 2010, vol. 66, no. 24, p. 4292-4297

A new sensing molecule containing aza-15-crown-5 as a receptor and 4- (phenyldiazenyl)naphthalen-1-ol as a signal converter has been synthesized. In the free ligand, the hydrogen bonding between the tautomeric OH group and the nitrogen atom from the macrocycle fully shifts the tautomeric equilibrium towards the enol form. The complexation reverses the equilibrium as a result of the strong...