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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...