Synthesis and Structural Evaluation of Neutral Acyclic Receptors for Recognition of Ionic Analytes in Solid- and Solution-State

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This thesis deals with „supramolecular host-guest recognition chemistry‟ where the host mainly anions or the hydrated anions or anionic associations are formed by some simply synthesized monopodial or dipodal acyclic receptors (L1-L6) decorated by the positional or electronic effect of terminal aryl substituents or anionic dimension or molecular host architectures in solid-state. Interestingly the dipodal receptors L1-L4 formed various halides/hydrated halide complexes whereas, among simple monopodial receptors L5 and L6, only L5 could be able to form a dimeric association of [HCO3⋯HCO3]2− as well as of [HSO4⋯HSO4]2− which were supported by various non-covalent supramolecular interactions. Like dipodal receptors (L1-L4), monopodial receptors L5 and L6 also displayed the tendency to form various halide/hydrated halide complexes at room temperature. On the other hand, we are also interested in solution-state recognition of various ionic analytes in a physiological medium. To aim that, at first, we have designed two simple pyrene/anthracene-based chemodosimeters namely, L7 and L8 connected through a C=C bond-forming D-π-A-type structure to facilitate interactions with ionic species where we have verified and studied the reactivity of C=C double bonds towards colorimetric (LOD = 0.09 ppm for L7 and 0.76 ppm for L8) and fluorometric (LOD = 0.55 ppm at 376 nm and 0.053 ppb at 455 nm for L7 whereas 0.85 ppm for L8) sensing of HSO3− based on Michael-type addition reaction in a mixed aqueous medium. To prove the feasibility of the probe in practical applications, we used L7 for the quantitative detection of HSO3 - in food, water samples, and dip-stick analysis.
Supervisor: Das, Gopal
Supramolecular Chemistry, Host-guest Chemistry, Sensor