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Single-crystal-to-single-crystal synthesis of a pseudostarch via topochemical azide–alkyne cycloaddition polymerization† † Electronic supplementary information (ESI) available. CCDC 2038869 and 2038870. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/d1sc03727g


ABSTRACT: There is high demand for polysaccharide-mimics as enzyme-stable substitutes for polysaccharides for various applications. Circumventing the problems associated with the solution-phase synthesis of such polymers, we report here the synthesis of a crystalline polysaccharide-mimic by topochemical polymerization. By crystal engineering, we designed a topochemically reactive crystal of a glucose-mimicking monomer decorated with azide and alkyne units. In the crystal, the monomers arrange in head-to-tail fashion with their azide and alkyne groups in a ready-to-react antiparallel geometry, suitable for their topochemical azide–alkyne cycloaddition (TAAC) reaction. On heating the crystals, these pre-organized monomer molecules undergo regiospecific TAAC polymerization, yielding 1,4-triazolyl-linked pseudopolysaccharide (pseudostarch) in a single-crystal-to-single-crystal manner. This crystalline pseudostarch shows better thermal stability than its amorphous form and many natural polysaccharides. Prudent crystal engineering allows head-to-tail arrangement of inositol monomer molecules pre-organizing azide and alkyne units of adjacent monomers in a ready-to-react manner. On heating regiospecific SCSC polymerization yields a starch-like polymer.

SUBMITTER: Ravi A 

PROVIDER: S-EPMC8442703 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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