Polyaniline/Aza-Bicyclo Composites Containing P, S, and Si Atoms: Synthesis, Characterization, Molecular Orbital Calculations, Electrical Conductivity, and Biocidal Activities against Some Biofouling-Causing Organisms

Abstract

1,3-Dipolar cycloaddition reaction of 3-hydroxy-1-(2-oxo-2-phenylethyl) pyridinium bromide (1) or 3-hydroxy-1-(3-nitrobenzyl) pyridinium chloride (2) with trimethylvinylsilane, methylsulfonyl chloride, and vinyl triphenylphosphonium bromide under the influence of sonoenergy leads to form six cycloadducts (3)–(8). The novel cycloadducts were characterized using Fourier transform infrared (FTIR) spectroscopy, mass spectroscopy (MS), and nuclear magnetic resonance (1H-NMR). In situ formation of polyaniline (PANI) composites in the presence of 0.1 g of each cycloadduct (CYC) led to form eight PANI/CYC composites (9)–(16). The newly synthesized composites were characterized by using transmission electron microscopy. All composites showed high electrical conductivity compared with PANI itself. The potential of new composites as anti-biofouling agents was evaluated. Compounds were observed to be the most potent antimicrobial/antifouling agents considering their toxicity against non-target sea organisms.