5-(2-Hydroxylphenyl)diazo-dipyrromethane: Synthesis, Structure and Fluoride Ion Detection

A new azopyrrole compound, 1, has been synthesized and characterized. The crystal of 1 is of monoclinic system, space group P2(1)/c with a = 8.7167(9), b = 17.5929(19), c = 12.8096(15) angstrom, beta = 97.565(2)degrees, V = 1947.3(4) angstrom(3), Z = 4, C20H26N4O2, M-r = 354.45, D-c = 1.209 g/cm(3), F(000) = 760 and mu(MoKa) = 0.080 mm(-1). In the crystal, 1 binds one methanol molecule through N-H center dot center dot center dot O, O-H center dot center dot center dot O and O-H center dot center dot center dot pi interactions. UV-Vis titration and H-1 NMR titration studies reveal that compound 1 can selectively detect fluoride ion in the DMSO solution.