Engaging the Reversible Bonds of an Immobilized Styreno-Thiophene Film

Abstract

The Gewald reaction was used to make a 2,5-diaminothiphonene that was functionalized with two styrene monomers. It was condensed with 2,5-thiophene dicarboxaldehyde to afford a conjugated azomethine triad. The X-ray crystallographic structure of the red-colored azomethine confirmed the antiparallel arrangement and the near-coplanarity of the three thiophenes. The terminal amines were also found to undergo both intra- and intermolecular hydrogen bonding with its ester carbonyl. Polymerization of the styrene functionalized azomethine was done in the solid state as thin films on glass substrates. The resulting red-colored film was electroactive and it changed to purple upon electrochemical oxidation. The reversible bonds in the cross-linked film retained their intrinsic dynamic character. They could be hydrolyzed to both their corresponding amine and aldehyde constitutional components, while also undergoing component exchange with aniline. These dynamic covalent bond forming reactions could be spectroscopically tracked courtesy of the intrinsic red color of the film.

Extending the Color Retention of an Electrochromic Device by Immobilizing Color Switching and Ion-Storage Complementary Layers

“…The substrates (either glass microscopes coverslips or ITO glass) were sonicated in water and 2-propanol and then they were exposed to an UV-ozone atmosphere. A layer of either 2 with the addition of a small amount (~2% mol) of AIBN or 1 was obtained by spray-coating a stock solution on the ITO-coated glass slides [61]. The substrates were then heated in a glovebox under nitrogen at 110 • C for 1 and 90 • C for 2 for at least 1 h. The substrates were cooled and the resulting films were thoroughly rinsed with dichloromethane and the air dried to evaporate any residual solvent.…”

Synthesis and Characterization of New Conjugated Azomethines End-Capped with Amino-thiophene-3,4-dicarboxylic Acid Diethyl Ester

“…The compounds containing the imine bond (–N=CH–) known as imines, azomethines or a Schiff bases are a group of materials of interest to many fields of science [ 1 , 2 , 3 , 4 , 5 ]. Azomethines were tested as electrochromic materials and for applications in medicine and pharmacology [ 6 , 7 , 8 , 9 ], in optical computers [ 10 , 11 ] and also as agents preventing the corrosion of mild steel, zinc, aluminum and copper in an acid environment (corrosion inhibitors) [ 12 , 13 ].…”

Reductive Electropolymerization and Electrochromism of Iron(II) Complex with Styrene-Based Ligand

“…The reductive electropolymerization of vinyl-substituted complexes has been also useful for the copolymerization of various metal complexes [11,19]. The polymerization of compounds containing styrene groups leading to formation of thin films on the electrode surface can also be done by radical polymerization reaction [20,21] but it usually requires the use of some additional initiators, such as AIBN or temperature to initiate the formation of free radicals.…”