Abstract
In recent years the research of sensors with good sensitivity and good selectivity in aqueous medium has been of great interest.1 Chemosensors soluble in aqueous media are very interesting, because of the importance in revealing a number of biological processes, disease states and environmental pollutions.2 2,4,5-Triaryl-imidazoles are versatile compounds with application in medicine, due to their biological activity, and materials sciences, for their interesting optical properties. These properties can be tuned by careful selection of substituents at positions 2, 4 and 5: replacement of the aryl group by a heterocyclic group results in larger π-conjugated systems with improved optical properties for application in nonlinear optics, OLEDs, DNA intercalators, and chemosensors.3 In this communication, we report the synthesis of new phenanthroimidazoles, substituted at position 2 with (hetero)aryl groups of different electronic character, in order to evaluate their photophysical properties and chemosensory ability. The new derivatives were characterized by the usual techniques and a detailed photophysical study was undertaken. The evaluation of the compounds as fluorimetric chemosensors was carried out by performing titrations in acetonitrile and acetonitrile/water in the presence of relevant organic and inorganic anions, and of alkaline, alkaline-earth and transition metal cations.
Highlights
In recent years the research on sensors with good sensitivity and selectivity in aqueous medium has been of great interest.[1]
For many fluorescent chemosensors the change in emission intensity by interaction with the analyte is measured, but a shift of the emission wavelength is a convenient means to monitor the sensing process.4 2,4,5-Triaryl-imidazoles are versatile compounds with application in medicine, due to their biological activity, and materials sciences, for their interesting optical properties. These properties can be tuned by careful selection of substituents at positions 2, 4 and 5: replacement of the aryl group by an heterocyclic group results in larger π-conjugated systems with improved optical properties for application in nonlinear optics, OLEDs, DNA intercalators, and chemosensors.[5]
Considering our current research interests in this theme,[4,5] we report the synthesis of new phenanthroimidazoles, substituted at position 2 witharyl groups of different electronic character, in order to evaluate their photophysical properties and chemosensory ability
Summary
In recent years the research on sensors with good sensitivity and selectivity in aqueous medium has been of great interest.[1]. The evaluation of the compounds as fluorimetric chemosensors was carried out by performing titrations in acetonitrile and acetonitrile/water in the presence of relevant organic and inorganic anions, and of alkaline, alkaline-earth and transition metal cations. Spectrophotometric and spectrofluorimetric titrations of compounds 2a-c Solutions of phenanthroimidazole derivatives 2a-c
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