Synthesis of 4-styrylphthalhydrazides and their chemiluminescence reaction. Emitters and chemiluminescence efficiency highly dependent on electronic nature of styryl goups
Abstract:A series of 4-styrylphthalhydrazides were synthesized and their chemiluminescence reactions were investigated. The chemiluminescence quantum yields as well as the emitters were variable depending on the electronic nature of the terminal substituents attached on the styryl groups. It was revealed that the excited phthalate ions were the emitters when they were highly fluorescent, while the energy transfer chemiluminescence from the excited phthalate ions to the phthalhydrazide anions took place when the fluores… Show more
Two 4-styrylphthalhydrazides bearing crown ether moieties as ionophores were prepared and their chemiluminescence behavior was investigated. Their aerobic oxidation in the presence of excess tert-BuOK in DMSO provided the chemiluminescence with much shorter emission wavelengths than those of the corresponding phthalate dianions, indicating that the emission arose from the excited pthalates incorporated with potassium ions at the ionophore sites.Such incorporation of potassium ions with the crown sites also reduced the fluorescence intensities of the phthalate dianions which caused an energy transfer chemiluminescence, resulting in the additional emissions of the phthalhydrazide monoanions in much longer wavelength regions. On the other hand, only the emission from the excited phthalate dianion was detected under aqueous conditions using aqueous hydrogen peroxide in acetonitrile as the oxidant, but no meaningful difference in the chemiluminescence intensity depending on the kind of metal cations was observed.
Two 4-styrylphthalhydrazides bearing crown ether moieties as ionophores were prepared and their chemiluminescence behavior was investigated. Their aerobic oxidation in the presence of excess tert-BuOK in DMSO provided the chemiluminescence with much shorter emission wavelengths than those of the corresponding phthalate dianions, indicating that the emission arose from the excited pthalates incorporated with potassium ions at the ionophore sites.Such incorporation of potassium ions with the crown sites also reduced the fluorescence intensities of the phthalate dianions which caused an energy transfer chemiluminescence, resulting in the additional emissions of the phthalhydrazide monoanions in much longer wavelength regions. On the other hand, only the emission from the excited phthalate dianion was detected under aqueous conditions using aqueous hydrogen peroxide in acetonitrile as the oxidant, but no meaningful difference in the chemiluminescence intensity depending on the kind of metal cations was observed.
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