The title trifluoroacetylaminophthalimide derivative produced a violet fluorescence (lambdaFLmax 392 nm) in MeCN, and it displayed a green emission (lambdaFLmax 506 nm) after irradiation at 254 nm in the presence of iodide ions. The corresponding amidate ion of the trifluoroacetamide was identified as the green fluorescence emitter. The deprotonation reaction may be caused by proton-abstracting solvated electrons generated by a photochemical charge--transfer-to-solvent process from I(-) to MeCN.
The novel azacrowned phthalimide 1 has been prepared and its fluorescence properties have been investigated by addition of EtOH and Ag+. The phthalimide 1 showed appreciable solvatofluorochromism; its fluorescence maxima (λFL) appeared in the wavelength region between 458 (in Et2O) and 544 nm (in EtOH). In benzene, the phthalimide 1 gave off blue emission (λFL 466 nm) while it emitted green fluorescence (λFL 497 nm) upon addition of 250 mM of EtOH. Both the blue and the green emissions were quenched by Ag+. Potential logic operations of the phthalimide 1 were examined using fluorescence outputs at 450 (Out1) and 515 nm (Out2) and two input stimuli, EtOH (In1) and Ag+ (In2). The Out1 was on in the absence of these inputs while its intensity was reduced (off) by either or both of the inputs to serve as a NOR operator. The Out2 was off without the inputs; in contrast, the intensity of Out2 was enhanced (on) by In1. The enhanced Out2 was switched off by In2. The Out2, thus, corresponds to an INHIBIT operation responding to the input signals. The crowned phthalimide 1 mimics a two-input–two-output combinational logic gate with a single fluorophore and a single ion-sensing unit.
The novel azacrowned phthalimide (I), obtained by a one-step crowning reaction, shows both solvent and metal-cation sensitivity. It mimics a two-input-two-output logic circuit with a single fluorophore and a single guest-sensing function. The molecular design provides a basis for a novel multiple-color output molecular-sensing device with a simple molecular structure. -(OKAMOTO*, H.; KOHNO, M.; SATAKE, K.; KIMURA, M.; Bull. Chem.
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