Université de Fribourg

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

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

Université de Fribourg

Solid state tautomerism in 2-((phenylimino)methyl)naphthalene-1-ol

Nedeltcheva, Daniela ; Kamounah, Fadhil S. ; Mirolo, Laurent ; Fromm, Katharina M. ; Antonov, Liudmil

In: Dyes and Pigments, 2009, vol. 83, no. 1, p. 121-126

The solid state tautomerism of 2-((phenylimino)methyl)naphthalene-1-ol was studied using X-ray measurements and absorption spectroscopy. In the solid state, the keto tautomer predominates. The observed shift in the equilibrium from the enol (dilute solution) to the keto (solid state) forms is explained by the formation of dye aggregates using ab initio quantum chemical calculations.