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Synlett 2020; 31(12): 1167-1171
DOI: 10.1055/s-0040-1707947
DOI: 10.1055/s-0040-1707947
letter
Organocatalytic Ring-Opening Polymerization Strategies for Synthesis of Poly(phosphothioesters) with a Pendent Phenyl Group
We gratefully acknowledge the generous support by the National Natural Science Foundation of China (21901249, 21950410529), National Key R&D Plan (2017YFC1104800), Taishan Scholar Foundation of Shandong Province (tsqn201812112), and the “135” Projects Fund of Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences.Further Information
Publication History
Received: 24 March 2020
Accepted after revision: 21 April 2020
Publication Date:
05 May 2020 (online)
Abstract
A novel type of phosphothioester substrate, 2-phenyl-1,3,2-dioxaphospholane 2-sulfide (PTP), has been synthesized and subjected to ring-opening polymerization. DBU/thiourea served as an efficient cooperative organocatalyst for the synthesis of poly(PTP), delivering the polymer with a well-defined structure, a relatively narrow molecular-weight distribution (1.14–1.20), and high molecular weight (up to 45.2 kg/mol). The ring-opening polymerization process showed a controlled/living nature. In addition, diblock copolymers of PTP with rac-lactide with well-defined structures were also synthesized.
Key words
organocatalysis - ring-opening polymerization - polyphosphothioesters - living polymerization - phenyldioxaphospholane sulfide - block copolymerizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707947.
- Supporting Information
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- 22 Poly(2-phenyl-1,3,2-dioxaphospholane 2-sulfide) (Table [1], Entry 9) In a typical polymerization reaction, a 5 mL Schlenk tube equipped with a stirring bar was dried and charged with argon three times, and then placed in a glovebox. In the glovebox, TU (7.4 mg, 0.02 mmol), a 1 M solution of DBU in toluene (20 μL, 0.02 mmol), a 1 M solution of PPA in toluene (20 μL, 0.02 mmol), CH2Cl2 (0.5 mL), and PTP (100 mg, 0.5 mmol) were added sequentially to the Schlenk tube. The tube was then removed from the glovebox and kept in an ice bath for 20 min. The reaction was quenched by addition of a 1 M solution of AcOH in CH2Cl2 (50 μL). The polymer was precipitated several times from cold Et2O, and dried under vacuum to a constant weight. The molecular-weight distribution and number-average molecular weight of the polymer were determined by GPC: M n = 4400 g/mol; Ð = 1.19.