Biosourced Cyclic and Multicyclic Polyesters Based on 1,4:3,6-Dianhydrohexitols: Application to Metal Ions Uptake in Aqueous Media

Authors want to thank all INRAP staff for analysis and helpful discussion. M. Mezni is acknowledged for NMR experiments, R. Jebali and N. Chaabane for ICP analysis.International audienceIsosorbide and isomannide are polycondensed in solution with trimesoyl chloride at a concentration of 0.06 mol L-1 for the synthesis of cyclic and multicyclic polyesters. The feed ratio diol/trimesoyl chloride is varied from 1.0/1.0 to 1.6/1.0. As all obtained polyesters prove insoluble, innovative solvent-free matrix assisted laser desorption ionization time-of-flight mass spectrometry (MALDI ToF MS) is performed for their characterization. The influence of the stereochemistry is shown to be of great importance for the cyclization trend. Both isosorbide and isomannide lead mainly to cyclic and multicyclic structures at a feed ratio of 1.0/1.0 and 1.1/1.0. Isomannide gives higher fractions of multicyclic structures. The products are characterized by complementary techniques such as C-13 cross polarization magic angle spinning nuclear magnetic resonance (C-13 CP-MAS NMR) and differential scanning calorimetry measurements. Application as a cryptands for the uptake of metal ions in aqueous media is followed by inductively coupled plasma atomic emission spectroscopy (ICP AES) analysis and reveal efficient toward large range of metals with tunable selectivity depending on the starting diol

Hyperbranched cyclic and multicyclic poly(etherketone)s by polycondensation of isosorbide and isomannide with 2,6,4′-trifluorobenzophenone and 1,3,5-tris(4-fluorobenzoyl) benzene

International audience1,3,5-Tris(4-fluorobenzoyl)benzene (TFBB) and 2,6,4′-trifluorobenzophenone (TFB) were polycondensed with isosorbide and isomanide. All polycondensations were performed in a mixture of dimethyl sulfoxide and toluene with potassium carbonate as promotor. Optimal concentration to avoid gelation was set at 0.06 mol L−1. The different cyclization tendencies on the basis of monomers conformations are discussed. In the TFB series, the feed ratio isosorbide/TFB was varied from 1.0:1.0 to 1.5:1.0. A majority of linear and hyperbranched species were identified as main reaction products by matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry regardless of the diol with slight cyclization tendency for isomannide. When TFBB was polycondensed with isosorbide, the cyclization tendency was significantly improved. The products obtained at a feed ratio of 1.41/1.0 and 1.51/1.0 were rich in cyclic and multicyclic species. More interesting results were obtained from the polycondensation of TFBB and isomannide, giving rise majoritarily to cyclic, bicyclic, and multicyclic species. Differential scanning calorimetric measurements indicated high glass transition temperature (around 200°C)