Chemiluminescence of 4‐styrylphthal‐hydrazides with crown ether as ionophore

Abstract

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.

Synthesis of 2,3-Anthracenedicarboxylic-acid-derived Fluorophore and Chemiluminophore Incorporating Dipicolylaminomethyl Receptors, and Their Luminescence Responses to Metal Ions

“…A few chemiluminophores incorporating crown ether moieties have been reported whose chemiluminescence feature were modified by alkali metal cations. [13][14][15][16][17] Motoyoshiya et al have investigated effects of host molecules, which possess dipicolylaminomethyl functionality as the electron donor, on a peroxalate chemiluminescence system. 18 They revealed that the host molecule effectively quenched the chemiluminescence, whereas addition of transition metal cations such as Zn 2+ and Cu 2+ to the chemiluminescence system recovered the chemiluminescence emission.…”

Chemiluminescence of 5-(azo-para-phenylene-N-aza-15-crown-5)-phthalhydrazide

“…21 Derivatives of luminol with azo-calixarenes 22 have also been reported to present weak FL and significant CL. Also phthalhydrazide-ionophores such as styrylphthalhydrazides with crown ethers 23 and aza-crowned isoluminol 24 were obtained.…”