Dimerization strategy towards higher carbon sugar alcohols as potential phase change materials

Abstract

Sugar alcohols are interesting candidates for phase change materials (PCMs). Their strong hydrogen bonding tendency gives them high thermal storage potentials. Recently, specific sugar alcohols with extended chain length have been predicted by computational calculations to possess remarkably high values of latent heat making them promising PCMs [1] (Scheme left). An even number of carbon atoms, no branching and all hydroxy groups in 1,3-anti orientation have been identified as prerequisite. However, experimental validation of these predictions is yet lacking as these materials are not readily available. We aim to make these PCM candidates accessible for thermal evaluation. In order to obtain higher sugar alcohols of C10 and longer chain length, we apply a dimerization approach [2]. Linking two sugar-derived building blocks by metathesis allows us to directly and efficiently translate the natural stereochemistry of the carbohydrates into our target materials. We have already succeeded in the homo-coupling of a D-arabinose derived building block to the D- manno-D-manno-decitol (manno-decitol, C10). Next, by combining differently sized precursors even higher sugar alcohols (C12, C14) are accessible via (cross) metathesis. The synthesized compounds are being investigated for their thermal properties and compared to their computationally estimated potentials.