Energy density in nonaqueous redox flow batteries (RFBs) is often limited by the modest solubility of the redox-active organic molecules (ROMs). In addition, the lack of a separator that prevents ROMs from crossing between anolyte and catholyte solutions necessitates the use of 1:1 mixtures of two ROMs in both the anolyte and catholyte solutions in symmetric RFBs, further limiting concentrations. We show that permanently cationic oligomers of viologen, tris(dialkylamino)cyclopropenium, and phenothiazine molecules have high solubility in acetonitrile and cross over an anion exchange membrane at slow to undetectable rates, enabling the creation of asymmetric RFBs with low crossover. No added supporting electrolyte is necessary, with only the PF 6 − counteranions of the ROMs crossing the membrane during charge/discharge. An oligomeric viologen + oligomeric cyclopropenium RFB at 1.0 M (redox equivalents) has a voltage of 1.66 V and a theoretical energy density of 22.2 Wh/L, one of the highest reported for nonaqueous RFBs.
A mild and efficient synthesis of a broad scope of substituted naphtho[1,2-a]pyrene derivatives was accomplished in good yields using an InCl 3 /AgNTf 2 -mediated two-fold alkyne benzannulation reaction. HPLC enantiomeric separation was achieved and the interconversion barriers have been determined. The ECD spectra of two derivatives were recorded and interpreted through TD-DFT calculations. Raman spectra were also recorded and predicted through DFT calculations.
A mild and efficient synthesis of a broad scope of substituted naphtho[1,2-<i>a</i>]pyrene derivatives was accomplished in good yields using an InCl<sub>3</sub>/AgNTf<sub>2</sub>-mediated two-fold alkyne benzannulation reaction. HPLC enantiomeric separation was achieved and the interconversion barriers have been determined. The ECD spectra of two derivatives were recorded and interpreted through TD-DFT calculations. Raman spectra were also recorded and predicted through DFT calculations.
A new synthetic methodology has been developed for the synthesis of dihydroisobenzofuran carboxaldehyde derivatives. The reaction proceeds by a silver‐catalyzed protodesilylation/5‐exo‐dig cyclization/oxidation reaction to provide a broad scope of products with yields ranging from 55–91 %. Control experiments show that protodesilylation precedes the 5‐exo‐dig cyclization step in the catalytic cycle. The synthetic utility of these highly functionalized products was showcased through a number of chemoselective chemical transformations.
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