Synthesis and Spectroscopic Properties of Acridinium-9-sulfonamides
Abstract By introducing an electro-withdrawing antipyrine group, N -( p -toluenesulfonyl)- N -(4-antipyrine)-10-methylacridinium-9-carboxamide triflate is prepared. The UV, fluorescent (FL), and chemiluminescent (CL) properties of the target compound and of its precursor are investigated by comparing with those of the model compounds N -( p -toluenesulfonyl)- N -phenyl-10-methylacridinium-9-carboxamide triflate and the corresponding precursor, respectively. The results show that, compared with the corresponding model compound, acridine sulfonamide with a heterocyclic antipyrine group exhibits blue shift of both UV absorption and of maximum excitation wavelength ( λ ex ) and the emission wavelength ( λ em ) in FL spectra. The λ ex of the final target and its precursor are 268 and 274 nm, respectively, and the λ em are 321 and 327 nm, respectively, whereas the λ ex of the model compound and its unmethylated precursor are 365 and 359 nm, respectively, and the λ em are 504 and 440 nm, respectively. Moreover, the chemiluminescence of the final target compound triggered by H 2 O 2 could finish within 1.1 s, and the quantum yield is similar to that of the model compound, being 5.6 times high as that of luminol.