Molecule Design Of Hypochlorite Ratiometric Probes And Tripodal Compounds

Hypochlorite is widely used in our daily lives as a disinfectant or a bleaching agent. Meanwhile, hypochlorite is one of the most important reactive oxygen species (ROS) in living organisms for its unique antibacterial properties in the immune system. However, overproduction of ClO-in vivo results in oxidative stress which is implicated in the pathogenesis of many diseases, such as arthritis, cancers, and neuron degeneration, so it is important for the detection of ClO-. In this thesis, two boronate-based ratiometric probes (Z1, Z2) were synthesized to detect hypochlorite anion based on the oxidation of C-B bond into C-O bond. The details are summarized as follows:In chapter2, two water soluble organoboronic acids Zl, Z2for the ratiometric detection ClO-anions were synthesized. The recognition properties of Zl and Z2were investigated by UV/vis and fluorescence spectra. Z1and Z2exhibited high sensitivity for CIO-in Na2HPO4-NaH2PO4. The detection limits of Zl and Z2were calculated to be2.5×10-7M and2.7×10-7M, respectively. Upon the addition of ClO-, the color of the solution changed immediately from colorless to red for both probes. The pH profiles of Zl and Z2in the absence and presence of ClO-were examined, which revealed that Zl and Z2can detect the ClO-anion over a wide pH span. For practical applicability, we conducted the experiments on test kits and the results showed that the discernible concentration of ClO-for Zl and Z2could be as low as1.0×10-4M and6×10-4M. We confirmed the validity of the proposed oxidation mechanism that ClO-oxidizes the C-B bond into C-O bond by ESI-HRMS.Tripodal receptors as ligand for transition metal complex and as receptor for cations and anions have been widely investigated. In this thesis, three tripodal compounds Nl, N2, and N3were synthesized and characterized. Their photophysical properties were investigated by UV/vis absorption spectrum and fluorescence spectrum in details. The impact factors which influence the photophysical properties of this type of dyes were disclosed. It is found that the water addition reaction to the charged C=N double bond is a key factor for the reaction breaking the conjugated system, which resulted the unstable photophysical properties of this type of dyes. Moreover, this reaction is temperature-, pH-, and solvent-dependent.