7-Oxa-2,3-diazanorbornene (ODAN): A One-Step Accessible Monomer for Living ROMP to Produce Backbone-Biodegradable Polymers

18 October 2023, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Traditional ring-opening metathesis polymerization (ROMP) reactions exhibit broad functional group compatibility and precise control over polymer architectures, albeit with non-biodegradable backbones. Recent progress has resulted in a series of biode-gradable ROMP products with diverse cleavable functional groups, yet the majority of the monomers display moderate to low ring strain, which restricts their living polymerization reactivity. In this study, a novel category of readily available 7-oxa-2,3-diazanorbornenes (ODAN) is presented, which exhibits the highest ring strain (22.8 kcal/mol) compared to existing degradable ROMP monomers. This trait endows ODAN with the ability to perform living polymerization reactions, generating narrowly dis-persed homopolymers, block copolymers, and statistical copolymers with various cyclic olefin comonomers, thereby enabling pre-cise control over distribution of the biodegradable functional groups. Additionally, the resultant polymers comprise directly con-nected allyl hemiaminal ether and urethane units, which are hydrolysable at controllable rates. Thus, these well-defined, structure-tunable, and backbone-biodegradable ROMP polymers are applied as nano-etching materials and biodegradable delivery carriers.

Keywords

Biodegradable polymers
Ring-opening metathesis polymerization
Living polymerization
Nano-etching materials
High ring-strain

Supplementary materials

Title
Description
Actions
Title
Supporting Information
Description
Experimental procedures, characterization, NMR, GPC, DSC, DFT calculation, and relevant discussions (PDF)
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.