Domino Polymerization for the Synthesis of Reductively Degradable Poly(disulfide)s With Arbitrary Side-Chain...

Area of Science:

• Polymer Chemistry
• Materials Science
• Organic Synthesis

Background:

• Conventional plastics pose environmental persistence challenges, necessitating the development of degradable alternatives.
• Poly(disulfide)s offer attractive properties like reductive degradability and environmentally triggered disassembly.
• Functional versatility in degradable polymers is crucial for diverse applications.

Purpose of the Study:

• To report a domino polymerization strategy for rapid and modular synthesis of functional poly(disulfide)s.
• To demonstrate the incorporation of diverse side-chain functionalities.
• To investigate the degradability and pH-responsive properties of the synthesized polymers.

Main Methods:

• Utilized a single monomer, N-(2-oxotetrahydrothiophen-3-yl)-3-(pyridin-2-yldisulfanyl)propanamide (PDTL), containing thiolactone (TL) and pyridyl disulfide (PDS) moieties.
• Initiated polymerization via TL ring-opening with amines, followed by disulfide exchange for chain propagation.
• Employed gel permeation chromatography and mass spectrometry to confirm reductive degradability.

Main Results:

• Successfully synthesized functional poly(disulfide)s with degradable main chains and diverse side-chain structures.
• Demonstrated incorporation of various functionalities including alkyl, allyl, propargyl, hydroxyl, carboxyl, amide, and tertiary amines.
• Confirmed reductive degradability and observed pH-responsive properties in poly(disulfide)s with dimethylamino groups, enabling tunable water solubility.

Conclusions:

• The domino polymerization strategy provides a rapid and modular route to functional poly(disulfide)s.
• The synthesized polymers exhibit tunable properties, including reductive degradability and pH responsiveness.
• This technique holds promise for developing advanced degradable polymers for various future applications.