Oligothiophene Nanoparticies: Photophysical and Electrogenerated Chemiluminescence Studies

Abstract

Thiophene oligomer nanoparticles (NPs) were studied by fluorescence spectroscopy and electrogenerated chemiluminescence (ECL). Distinct spectroscopic differences between aggregates or NPs of thiophene hexamers having differing substitution patterns of solubilizing alkyl groups were observed. The alpha,omega-unsubstituted thiophene hexamer, Hexamer-2, exhibited fluorescence properties that were similar in solution and as colloidal NPs; there was only a small red shift compared with what was observed for the discrete system dissolved in tetrahydrofuran (THF). In contrast, the oligomer substituted in the alpha,omega-positions with branched alkyl substituents (Hexamer-1) displayed a gradual bathochromic shift of the fluorescence maximum in proportion to the amount of a poor solvent (water) added to the THF solution. Moreover, the fluorescence characteristics for the oligomer(s) dissolved in a mixture of THF and water were similar to those seen by annihilation ECL in a mixture of benzene/acetonitrile. On this basis, we conclude that annihilation ECL may be a useful technique for monitoring the formation of organic nanoparticles.