Synthesis of some novel quinone diimine derivatives of benzo-15-crown-5 for application in Hg(2+) recognition.

A series of novel fluoroionophore bearing derivatives of benzo-15-crown-5 were synthesized by the amination of benzo-15-crown-5 followed by condensation with different quinones in the presence of titanium tetrachloride (TiCl4 ) and 1,4-diazabicyclo-[2.2.2]octane. The compounds were characterized by infrared, (1) H and (13) C nuclear magnetic resonance, mass spectroscopy and elemental analysis. Absorption and fluorescence spectral characteristics of these compounds were studied. It was observed that the anthraquinone derivative was acting as an Hg(2+) ion sensor.

2-Amino-7,7-dimethyl-5-oxo-4-[3-(trifluoro-meth-yl)phen-yl]-1,4,5,6,7,8-hexa-hydro-quinoline-3-carbonitrile.

In the title mol-ecule, C19H18F3N3O, the dihydro-pyridine and cyclo-hexene rings both adopt sofa conformations. The five essentially planar atoms of the dihydro-pyridine ring [maximum deviation = 0.039 (2) Å] form a dihedral angle of 88.19 (8)° with the benzene ring. The F atoms of the trifluoro-methyl group were refined as disordered over two sets of sites in a 0.840 (3):0.160 (3) ratio. In the crystal, N-H⋯O and N-H⋯N hydrogen bonds link mol-ecules into a two-dimensional network parallel to (100).