Ugi reactions with CO2 : access to functionalized polyurethanes, polycarbonates, polyamides, and polyhydantoins

Area of Science:

• Polymer Chemistry
• Organic Synthesis
• Sustainable Materials

Background:

• Carbon dioxide utilization remains a significant challenge in chemistry.
• Developing efficient methods for CO2 incorporation into polymers is crucial for sustainability.
• Novel polymerization strategies are needed to create advanced polymer architectures.

Purpose of the Study:

• To introduce a novel strategy for incorporating carbon dioxide into polymers.
• To synthesize step-growth monomers using the Ugi five-component condensation (Ugi-5CC) with CO2.
• To explore the synthesis of various polymers including polyurethanes, polycarbonates, polyamides, and polyhydantoins.

Main Methods:

• Utilizing the Ugi-5CC reaction with an alcohol, CO2, an amine, an aldehyde, and an isocyanide to form monomers.
• Polymerization of monomers via thiol-ene reaction to yield polyurethanes.
• Polycondensation with diphenyl carbonate to produce alternating polyurethane-polycarbonates.
• Direct synthesis of polyamides using bifunctional Ugi-5CC components.
• Conversion of polyamides to polyhydantoins.

Main Results:

• Successfully incorporated carbon dioxide into polymer backbones using the Ugi-5CC reaction.
• Synthesized diversely substituted polyurethanes and alternating polyurethane-polycarbonates.
• Obtained a novel polyamide with methyl carbamate side chains (M¯n = 19,850 g mol⁻¹).
• Achieved straightforward conversion of the synthesized polyamide into polyhydantoin.

Conclusions:

• The Ugi-5CC reaction provides a versatile platform for CO2 incorporation into polymers.
• This strategy enables the synthesis of various polymer types with tunable properties.
• The developed methods offer a sustainable route to functional polymers and advanced materials.