To improve the photochemical stability of α-terthiophene (3T) in air, we purposely introduced a naphthalene unit into its conjugated backbone, resulting in a fluorescent compound, 5-(1-naphthyl)-2,2':5',2''-terthiophene (NA-3T). The compound was further employed as a sensing element for the fabrication of a monolayer-chemistry based fluorescent sensing film. It was demonstrated that the fabricated film is highly sensitive and selective to the presence of picric acid (PA). The detection limit was found to be 3.2 × 10(-7) mol/L. The high sensitivity of the film to PA has been attributed to the specific binding of the film to the analyte because of proton transfer from PA to the amino group in the spacer, which is in accordance with the static nature of the quenching as revealed by fluorescence lifetime measurements. Further experiments demonstrated that the sensing process is fully reversible and free of interference from common organic solvents, acids and bases, etc. In addition, the film is stable, at least, within half a year provided it is properly preserved. More importantly, the present work makes it possible to use oligothiophenes as a new class of sensing elements, which may combine the advantages of conjugated polymers or oligomers and those of fluorescent compounds of low-molecular masses. This effort enlarges, definitely, the applications of oligothiophenes and the space for creating monolayer-chemistry based fluorescent sensing films.
© 2011 American Chemical Society