Exploring Green Chemistry Polymerizations for Sustainably Derived Building Blocks
Disciplines
Organic Chemistry
Abstract (300 words maximum)
Conjugated molecules and polymers have received significant attention in the area of thin-film electronics due to the ability to systematically tune optoelectronic properties and the potential for high-throughput solution processing protocols. Traditionally, thiophene-based building blocks have been used to accomplish this however, they are derived from nonrenewable petroleum resources and have negative consequences on the environment. Furan-based monomers represent a class of building blocks derived from biorenewable feedstocks blocks but are not traditionally known to participate in green chemistry polymerizations. This presentation will describe efforts exploring the feasibility of using furan-based building blocks in C-H activated direct arylation cross-coupling reactions and polymerizations. Specifically, molecular reactions involving a diester-functionalized furan and bromobenzene will be described to provide a proof-of-concept for the cross-coupling to occur. Guided by these results, including optimized catalyst, solvent, ligands, and reaction temperature, direct (hetero)arylation polymerizations (DHAP) will be performed and fundamental structural properties will be reported. These results will lay the foundation for green chemistry protocols within the realm of sustainable monomers and accessing a new family of conjugated polymers.
Academic department under which the project should be listed
CSM - Chemistry and Biochemistry
Primary Investigator (PI) Name
Graham Collier
Exploring Green Chemistry Polymerizations for Sustainably Derived Building Blocks
Conjugated molecules and polymers have received significant attention in the area of thin-film electronics due to the ability to systematically tune optoelectronic properties and the potential for high-throughput solution processing protocols. Traditionally, thiophene-based building blocks have been used to accomplish this however, they are derived from nonrenewable petroleum resources and have negative consequences on the environment. Furan-based monomers represent a class of building blocks derived from biorenewable feedstocks blocks but are not traditionally known to participate in green chemistry polymerizations. This presentation will describe efforts exploring the feasibility of using furan-based building blocks in C-H activated direct arylation cross-coupling reactions and polymerizations. Specifically, molecular reactions involving a diester-functionalized furan and bromobenzene will be described to provide a proof-of-concept for the cross-coupling to occur. Guided by these results, including optimized catalyst, solvent, ligands, and reaction temperature, direct (hetero)arylation polymerizations (DHAP) will be performed and fundamental structural properties will be reported. These results will lay the foundation for green chemistry protocols within the realm of sustainable monomers and accessing a new family of conjugated polymers.