Abstracts

b-Carbolines (i.e.,9H-pyridine[3,4-b]indole) compose a class of naturally occurring alkaloids, characterized by the presence of a pyridine ring fused to an indole moiety, with significant biological activity. In this study, fourteen compounds were synthesized, varying the benzaldehyde derivative which was attached to the carboline skeleton. The compounds were identified, and its purity confirmed by ¹H- and ¹³C-NMR, as well as melting points. The molar extinction coefficients show to be in the range of p-p* transitions and the fluorescence quantum yields range from 0.01 to 0.3, indicating that the substituents in the 1-position have a significant impact on the photophysical properties of these compounds. Furthermore, the fluorescence quantum yields indicate that these b-carbolines have potential utility as activators in peroxyoxalate chemiluminescence (CL). The synthetized carboline derivatives have been tested as activators in peroxyoxalate CL, using initially bis(2,4,6-trichlorophenyl) oxalate (TCPO) as reagent and imidazole as base and nucleophilic catalyst in organic solvents. The results indicate that these compounds act as activator in this CL transformation, although their efficiency showed to be considerably lower than commonly utilized polycondensed aromatic hydrocarbons. Some of the derivatives studied showed different kinetic behavior from its expected role as only CL activator, indicating that the carbolines could have multiple functions in the transformation, as activator but also potential base catalyst.