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Condensation and Polycondensation of Terephthaldehyde with Methyl D ‐Hexopyranosides
Author(s) -
MaślińskaSolich Jolanta
Publication year - 2001
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/1616-5195(20011001)1:7<312::aid-mabi312>3.0.co;2-j
Subject(s) - condensation polymer , chemistry , comonomer , polymer chemistry , condensation , polymer , surface modification , condensation reaction , nuclear magnetic resonance spectroscopy , molecule , diastereomer , proton nmr , organic chemistry , catalysis , copolymer , physics , thermodynamics
The condensation and polycondensations of terephthaldehyde ( 1 ) and methyl D ‐hexopyranosides (gluco‐, galacto‐ and mannopyranoside) are described. Methyl α ‐ D ‐glucopyranoside and methyl α ‐ D ‐galactopyranoside react with 1 to give mono‐ 5 a and 6 a and diacetals 5 b and 6 b . Their structures were confirmed by NMR and IR spectroscopy. The polycondensation of methyl α ‐ D ‐mannopyranoside ( 4 ) with 1 was studied in various solvents within the temperature range of 80–140°C. Regardless of the conversion or the initial comonomer feed ratios the composition of polycondensates depended on the reaction conditions leading to the formation of materials with diverse solubilities, molecular weights and optical properties. The regioselective polycondensation of 1 and 4 was examined by the 1 H NMR spectroscopy of polymer 7 . In the case of five‐membered cyclic acetal units, mixtures of the endo ‐H and exo ‐H dioxolan‐2‐yl system diastereomers are formed. Experimental examples of functionalization via ester units in polymer molecules 8 are described and the efficiency of the reaction routes and procedures are evaluated. The molecular weight was estimated by size‐exclusion chromatography (SEC) measurements before and after the functionalization.