Here we present a novel methodology to measure the alkaline stability of anion conducting polymers to be used as anion exchange membranes and anion exchange ionomers for fuel cells. The new ex situ technique simulates the environment of an anion exchange membrane fuel cell (AEMFC) during operation, where nucleophilic and basic OH − species in the absence, or with a scarce amount of water, attack the functional groups of the ionic polymer. Using this technique, we clearly show the critical effect of water molecules on the alkaline stability of quaternary ammonium (QA) cations commonly used as functional groups in AEMFCs. The results show that as the water content is reduced, the QA cations are more rapidly degraded in the presence of OH − at room temperature. With an increasing number of water molecules solvating the hydroxide, its nucleophilicity and basicity are hindered, and the QA degradation is significantly slowed. These results indicate that the currently used aqueous alkali ex situ tests to measure anion exchange membrane (AEM) stability may lead to false positive stability results where anion conducting polymers may appear more alkali stable than they really are.

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A transition-metal-free procedure for the N-arylation of tertiary amines to sp(3) quaternary ammonium salts is described. The presented conditions allow for the isolation of trialkylaryl, dialkyldiaryl, and novel triarylalkyl ammonium salts, including N-chiral quaternary ammonium salts. The reaction works at room temperature, open to air with electron-rich or -poor benzyne precursors and different tertiary amines, allowing the synthesis of a broad range of N-aryl ammonium salts that have applications in a variety of fields.

Phthalides have been synthesized exclusively in one pot via Pd-free Sonogashira coupling.

A novel and efficient methodology has been developed for the intramolecular aryl C–H oxidative lactonization of 2-arylbenzaldehyde using a low-cost CuCl catalyst and TBHP as the oxidant at room temperature.