Tetrazole as a Carboxylic Acid Isostere and the Synthesis of All Amine‐Based Polyampholytes

Abstract

A new family of polyampholytes (PAMs) is described in which both the basic and acidic groups are based on nitrogen functional groups. Reversible addition-fragmentation chain transfer-prepared poly(pentafluorophenyl acrylate) is quantitatively modified sequentially with 3-picolylamine and 5-aminotetrazole, yielding the new well-defined statistical PAMs. Successful formation of the PAMs is confirmed via a combination of 19 F and 13 C NMR spectroscopy and FTIR. Aqueous electrophoresis indicates isoelectric points (pI) between 2.9 and 4.4 depending on copolymer composition. However, the pI is somewhat insensitive to the copolymer composition, a feature attributed to the similarity of the pK a s of the acid tetrazole species and the conjugate acid of the pyridyl repeat units.

Tetrazole functionalization: A new strategy toward stable ion-solvating polymer electrolytes for alkaline water electrolysis

“…While the pKa of the benzimidazole units of m-PBI is around 12.8, [41] tetrazoles are considerably more acidic with a pKa value close to that of acetic acid. [42] The relatively strong acidity implies that the ionic potassium tetrazolide form of both STz25 and STz30 predominates under all conditions considered in this work as the pH of the solutions are far higher than the pKa of the tetrazole pendants, [43] as also supported by the DFT results show in Figure 1c. The high degrees of ionization make the polymers highly polar in alkaline environment, which promotes extensive electrolyte uptake.…”

Hydrolysis-resistant heterogeneous photocatalysts for PET-RAFT polymerization in aqueous environments

“…Light-mediated polymerization in water in particular shows signicant potential to broaden the scope of accessible materials that can be synthesized under visible light and ambient conditions. [19][20][21][22][23][24] This includes reversible deactivation radical polymerization (RDRP) to produce well-dened (super)hydrophilic polyelectrolytes, 25,26 zwitterionic materials, 27,28 or polyampholytes, 29 all of which have been considered intriguing materials for various applications, including anti-fouling, 30 anti-icing, 31 anti-fogging, 32 and many others. 33,34 Moreover, water as a solvent for RDRP can provide exciting new chemical behaviors to drive unconventional reaction pathways and accelerate advancements in photocatalysis.…”

Supramolecular Cu(ii) nanoparticles supported on a functionalized chitosan containing urea and thiourea bridges as a recoverable nanocatalyst for efficient synthesis of 1H-tetrazoles

“…Indeed, not only the p K a of tetrazolyl moiety is close to the –COOH functional group, but also it has nearly the planar delocalized system space requirements and provides maximum nitrogen content of any heterocyclic compound. 102 Hence, tetrazole moiety can be considered as a bioisosteric alternative analogue for the carboxylic acid, Cl-amidine, or furan ring ( Fig. 1a ).…”