Chain-Growth Sulfur(VI) Fluoride Exchange Polycondensation: Molecular Weight Control and Synthesis of Degradable Polysulfates
Year: 2021
Type: article
Abstract: Sulfur(VI) fluoride exchange (SuFEx) click chemistry has offered a facile and reliable approach to produce polysulfates and polysulfonates. However, the current SuFEx polymerization methods lack precise control of target molecular weight and dispersity. Herein, we report the first chain-growth SuFEx polycondensation process by exploiting the unique reactivity and selectivity of S-F bonds under SuFEx catalysis. Given the higher reactivity of iminosulfur oxydifluoride versus fluorosulfate, the chain-growth SuFEx polycondensation is realized by using an iminosulfur oxydifluoride-containing compound as the reactive chain initiator and deactivated AB-type aryl silyl ether-fluorosulfates bearing an electron-withdrawing group as monomers. When 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was utilized as the polymerization catalyst, precise control over the polymer molecular weight and polydispersity was achieved. The resulting polymers possess great thermal stability but are easily degradable under mild acidic and basic conditions.
Source: ACS Central Science
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
Funders: National Science Foundation, U.S. Department of Energy, Boston College, National Institutes of Health, Office of Science, University of California, San Diego, Materials Research Science and Engineering Center, Harvard University, National Institute of General Medical Sciences, Division of Materials Research, Division of Chemistry, Basic Energy Sciences, Materials Research Science and Engineering Center, University of California, San Diego
Awards: G1186292489, G1286236842, G1286251239, G1414775356, G1445641779, G1816284028, G1863003419, G3059826279, G30714459, G3083819904, G365575497, G382641700, G419881185, G42916606, G4501827968, G4796240486, G498139845, G5094606986, G5282220012, G5334459971, G5849692847, UC San Diego MRSEC: an NSF Materials Research Science and Engineering Center, G650090426, Sulfur(VI) Fluoride Exchange (SuFEx) Click Chemistry in Macromolecule Synthesis and Fabrication, G805243471, G8412107296, G8692219177, Chemoenzymatic glycan editing for deciphering biological functions of glycans, G969889393
OpenAlex ID: W3210934096