Research on even-odd effects of bio-based Nylon nF salts

Abstract

Nylon nF is a type of bio-based Nylon, whose raw materials NH2-(CH2)n-NH2 and 2,5-furandicarboxylic acid (FDCA) are both prepared by biological methods. The Nylon nF salts (PAnF salts) are the monomer salts before the polymerization of Nylon nF, whose product quality has a significant impact on the properties of Nylon nF. In this study, Nylon nF salts of FDCA and seven NH2-(CH2)n-NH2 diamines were synthesized. The crystal structures and thermodynamic behaviors of these Nylon salts were determined and analyzed by single crystal X-ray diffraction (SCXRD), powder X-ray diffraction (PXRD), and thermogravimetric analysis-differential scanning calorimetry (TG-DSC). Based on the analysis of melting point and solubility data, it was found that there is a significant even–odd effect between Nylon nF salts (n = 4–10). Moreover, the lattice energy and solvation energy in methanol of these Nylon salts were calculated by Materials Studio (MS) and Gaussian, respectively. The results indicated that there was also an even–odd effect in the lattice energy of Nylon nF salts. It is speculated that these even–odd phenomena were related to the symmetry of the ligand diamines and the stacking mode of Nylon salts. The study of the even–odd effect is significant in predicting and designing the physicochemical properties of cocrystals.