Cyclobenzoins for Energy Industries

Porous molecular crystals are an emerging class of porous materials with properties reaching and exceeding their polymeric counterparts, metal organic frameworks and covalent organic frameworks. They are composed of discrete molecules containing intrinsic voids or inefficiently packed to create extrinsic pores. Porous molecular crystals have been studied for a variety of applications from more traditional catalysis and gas separations to innovative utilizations in porous liquids and analytical sensing devices. Herein we focus on cyclotetrabenzoins, macrocycles synthesized through benzoin condensation cyclooligomerization of dialdehydes, for applications in energy industries. Chapter 1 introduces porous molecular crystals and discusses their studies in chemical separations, molecular sensing, catalysis, porous liquids, and proton conduction. Chapter 2 focuses on an esterified cyclotetrabenzoin for CO2/CO separation through pressure swing adsorption. Chapter 3 discusses a strategy to systematically expand the extrinsic porosity of cyclotetra(bisarylhydrazone)benzils and the utilization of their virtual pores for iodine capture in the solid state and from solutions. Chapter 4 presents two expanded cyclotetrabenzoins and their oxidation into redox-active cyclotetrabenzils which can be incorporated into organic cathode materials for lithium-ion batteries.