Electrochemical synthesis of poly(3-aminophenylboronic acid) in ethylene glycol without exogenous protons

Abstract

A non-aqueous solution of tetra-n-butylammonium fluoride (TBAF) in ethylene glycol has been tried for the first time as a supporting electrolyte for the electropolymerization of 3-aminophenylboronic acid (APBA). Unlike the traditional acidic aqueous solution, the present medium needs no exogenous protons; moreover, the presence of CF3COOH is found to be unfavorable for the polymerization. The protons are in situ generated by the reaction between the boronic acid group on APBA and 1,2-dihydroxyl on ethylene glycol. So, ethylene glycol serves as not only the solvent but also the proton source. As a part of the supporting electrolyte, F(-) is found to be involved in the electrochemical synthesis of poly(3-aminophenylboronic acid) (PAPBA), but it is not indispensable. Studies on the electropolymerization process indicate that the size of the ions in the electrolyte affects the rate of the doping/dedoping process. The smaller the cation, the easier the doping/dedoping process, and the better the stability of the grown film. As demonstrated by Fourier transform infrared spectra, UV-vis spectra, and scanning electron microscopy, the obtained PAPBA is a cross-linked nanoporous polymer membrane that has a good adherence to the glassy carbon electrode.

Alcohol Effect and the Related Mechanism on Fructose Dehydration into 5-Hydroxymethylfurfural in the Deep Eutectic Solvent of [Emim]Cl/Alcohol

“…Alcohols can be regarded to some extent as a type of green solvent. 21 These cheap solvents usually have low boiling points and can be easily recycled. There have been many reports on the dehydration of sugar to prepare HMF 22−28 or its derivative (its etherified product) 29−36 with an alcohol as solvent or cosolvent.…”

“…The major shortcomings of these media are their high volatility and their costly separation from the product. Alcohols can be regarded to some extent as a type of green solvent . These cheap solvents usually have low boiling points and can be easily recycled.…”

Hybrid Nanocomposite Platform, Based on Carbon Nanotubes and Poly(Methylene Blue) Redox Polymer Synthesized in Ethaline Deep Eutectic Solvent for Electrochemical Determination of 5-Aminosalicylic Acid

“…For polymer electrosynthesis, parameters such as surface tension, polarity, and viscosity have a strong influence on the structure of the films [13]. This has been shown for poly (3,4ethylenedioxythiophene) [14,15], polyaniline [16][17][18], 3-aminophenylboronic acid [19], polypyrrole [20,21], poly(acrylic acid) [22], poly(ethylene terephthalate) [23], poly(brilliant cresyl blue) [24], poly(thionine) [25], poly(methylene green) [26], and poly(neutral red) [27], mainly because of their control of monomer reactivity and mass transport properties.…”