Synthesis of water-soluble conducting polypyrrole with transition-metal tetrasulfonated porphyrins

Abstract

A novel catalytic route for the synthesis of a water-soluble and electrically conducting polypyrrole (PPy) in the presence of sulfonated polystyrene (SPS) is presented. Anionic water-soluble transition-metal tetrasulfonated porphyrins (TSPP) were used to catalyze the polymerization. The reactions were carried out with different monomer, catalyst, template and initiator concentrations and the optimum conditions are reported. Also various pH values ranging from 1 to 4 were investigated. The absorbance of the polaron bands at different pH values demonstrates that pH 2 is the best condition for polymerization. Precipitation or "salting out" phenomenon was highly dependent on the mentioned factors. The formation of PPy was confirmed by UV-vis and FT-IR spectroscopy. Cyclic voltammetry (CV) showed that the synthesized polymer has convenient electroactivity. Furthermore, the presence of SPS that serves as a charge-compensating dopant in this complex provides a unique combination of properties such as processability and water solubility.

Iron(III)‐porphyrin Complex FeTSPP: A Versatile Water‐soluble Catalyst for Oxidations in Organic Syntheses, Biorenewables Degradation and Environmental Applications

“…[25] Furthermore, a combination of 1 as a catalyst and hydrogen peroxide was used by Nabid et al for the oxidative polymerization of pyrrol-monomers leading to conductive polymers. [26] The analogous reaction with the horse radish peroxidase was also studied as a potential environmentally benign alternative compared to conventional oxidation methods, and by means of this approach poly-3,4-ethylendioxythiophene was successfully prepared. [26,27] Besides economical attractiveness, further advantages when using 1 are the high operational stability and activity of the catalyst at low pH-values.…”

“…[26] The analogous reaction with the horse radish peroxidase was also studied as a potential environmentally benign alternative compared to conventional oxidation methods, and by means of this approach poly-3,4-ethylendioxythiophene was successfully prepared. [26,27] Besides economical attractiveness, further advantages when using 1 are the high operational stability and activity of the catalyst at low pH-values. [26] The oxidation of primary and secondary alcohols was performed by Masoudian et al using immobilized 1 as a catalyst and hydrogen peroxide as an oxidation agent.…”

“…[26,27] Besides economical attractiveness, further advantages when using 1 are the high operational stability and activity of the catalyst at low pH-values. [26] The oxidation of primary and secondary alcohols was performed by Masoudian et al using immobilized 1 as a catalyst and hydrogen peroxide as an oxidation agent. [28] In a model reaction, benzyl alcohol (12) was oxidized to benzaldehyde (14) in a solvent mixture consisting of acetonitrile and water (1:1), leading to 6 % yield.…”

“…[6,18] For example Meunier et al investigated the oxidative degradation of organic halides in the presence of 1 with potassium monopersulfate or hydrogen peroxide. [23,33] To this type of compound class of organic halides belong anthropogenic pollutants such as 2,4,6-trichloro-phenol (26), which in part are hardly degradable or non-degradable by microorganisms and bioaccumulate in the tissue of animals and plants. [33] It was, however, reported that ligninases are suitable for degradation of organic halides.…”

Unraveling Synergistic Redox Interactions in Tetraphenylporphyrin–Polyluminol–Carbon Nanotube Composite for Capacitive Charge Storage

“…Porphyrin macrocycles are good candidates for capacitive charge storage due to their inherent large π-conjugated system with four pyrrole-like structures and their unique electronic structure that can act as both the electron donor and acceptor. − These types of macrocycles have been utilized in catalyzing the synthesis of water-soluble polypyrrole (PPy) and as doping agents for both PPy and polyaniline (PANI) to improve their respective electrical conductivities. − In energy storage, metal porphyrin deposited on a carbon nanotube (CNT) led to a reasonable electrochemical performance of ECs. However, the composites had limited cycling stability resulting in a steep decrease in charge storage performance. ,− …”