Arenedicarboximide Building Blocks for Fluorescent Photoinduced Electron Transfer pH Sensors Applicable with Different Media and Communication Wavelengths
摘要:
N-(aminoalkyl)-4-chloronaphthalene-1,8-dicarboximides 1, N-(aminoalkyl)-4-acetamidonaphthalene- 1,8-dicarboximides 3 and N,N'-bis(aminoalkyl)-perylene-3,4:9,10-tetracarboxydiimides 4 show good fluorescent off-on switching in aqueous alcoholic solution with protons as required for fluorescent PET sensor design. The excitation wavelengths lie in the ultraviolet (lambda(max) = 345 and 351 nm) for 1 and 3 and in the blue-green (lambda(max) = 528, 492 and 461 nm) for 4: the emission wavelengths lie in the violet (lambda(max) = 405 nm) for 1, in the blue (lambda(max) = 474 nm) for 3 and in the yellow-orange (lambda(max) = 543 and 583 nm) for 4. Compound 4b shows substantial fluorescence enhancement with protons when immobilized in a poly(vinylchloride) matrix, provided that 2-nitrophenyloctyl ether plasticizer and potassium tetrakis(4-chlorophenyl)borate additive are present to prevent dye crystalization and to facilitate proton diffusion into the membrane, respectively.