Synthesis and characterization of novel biosourced building blocks from isosorbide

Abstract

New biosourced unprotected diols were prepared by acylation reaction of aminoalcohol based on 1,4:3,6-dianhydrosorbitol (Isosorbide Is) with several aliphatic and aromatic diacyl chlorides (sebacoyl, adipoyl, and terephthaloyl). Optimization of reaction conditions (solvent, base nature, and addition mode) has been investigated with protected alcohols. The use of hindered bases was needful to ensure the selectivity of the addition reaction when starting from unprotected aminoalcohol, and selectively led to bis amides products with good yields. 1D and 2D NMR techniques were used to ascertain the structures of the unprecedented monomers. These novel building blocks were successfully polymerized using succinic and terephthalic spacers and studied by NMR and DSC techniques.