期刊
POLYMER CHEMISTRY
卷 4, 期 1, 页码 184-193出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2py20751f
关键词
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资金
- UGent
- TokyoTech
- Integrated Doctoral Education Program at TokyoTech
- The Kurata Memorial Hitachi Science and Technology Foundation
- KAKENHI [23106709, 23685022, 23350050]
- Grants-in-Aid for Scientific Research [23350050, 23685022] Funding Source: KAKEN
An efficient synthetic pathway toward cyclic polymers based on the combination of thiolactone and disulfide chemistry has been developed. First, heterotelechelic linear polystyrene (PS) containing an alpha-thiolactone (TLa) and an omega-dithiobenzoate group was synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization, employing a newly designed TLa-bearing chain transfer agent (CTA). The subsequent reaction of this heterotelechelic polymer with an amine, which acts as a nucleophile for both the TLa and dithiobenzoate units, generated the alpha,omega-thiol-telechelic PS under ambient conditions without the need for any catalyst or other additives. The arrangement of thiols under a high dilution afforded single cyclic PS (c-PS) through an oxidative disulfide linkage. The cyclic PS (c-PS) disulfide ring formation was evidenced by SEC, MALDI-TOF MS and H-1-NMR characterization. Moreover, we demonstrated a controlled ring opening via either disulfide reduction or thiol-disulfide exchange to enable easy and clean topology transformation. Furthermore, to illustrate the broad utility of this synthetic methodology, different amines including functional ones were employed, allowing for the one-step preparation of functionalized cyclic polymers with high yields.
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