Project Title

Elucidating the Effects of Sustainable Solvents on Polymerizations of Conjugated Monomers

Academic department under which the project should be listed

CSM - Chemistry and Biochemistry

Faculty Sponsor Name

Dr. Graham S. Collier

Human subjects were not used for this research.

Abstract (300 words maximum)

Synthesis of conjugated polymers is an extensive and potentially toxic process that traditionally requires multiple steps, toxic reagents, and nonrenewable solvents. The polymerization process of direct (hetero)arylation polymerization (DHAP) has eliminated the length and some of the toxic reactants/catalysts, but nonrenewable solvents are still used. Therefore, there is still a need to determine the viability of sustainable solvents for conjugated polymer synthesis via direct (hetero)arylation. Utilizing a newly synthesized halogenated monomer, dibromopyrrolo[3,2-b]pyrrole (Br2DPP), that is synthesized in a one-step process with nontoxic starting materials, this research will describe the copolymerization of DPP with thienopyrroledione (TPD). The synthesis is accomplished using an environmentally benign/sustainable polymerization process known as direct (hetero)arylation polymerization, while utilizing various sustainable solvents, such as 2-MeTHF. DHAP also will be used to produce the same polymer with both toluene, THF, and cyclopentyl methylether in order to determine the feasibility of using green solvents instead of nonrenewable solvents. Characterization of these polymers will show their molecular weights through gel-permeation chromatography (GPC), optical properties through both UV-Vis and fluorescence spectroscopies, and coupling defects through proton nuclear magnetic resonance (1H NMR) spectroscopy to validate the use of green solvents. Through this process, we will demonstrate that conjugated polymers can be synthesized using sustainable solvents, revolutionizing how conjugated polymers are synthesized and decreasing the environmental footprint left by the production of conjugated polymers.

Project Type

Event

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Elucidating the Effects of Sustainable Solvents on Polymerizations of Conjugated Monomers

Synthesis of conjugated polymers is an extensive and potentially toxic process that traditionally requires multiple steps, toxic reagents, and nonrenewable solvents. The polymerization process of direct (hetero)arylation polymerization (DHAP) has eliminated the length and some of the toxic reactants/catalysts, but nonrenewable solvents are still used. Therefore, there is still a need to determine the viability of sustainable solvents for conjugated polymer synthesis via direct (hetero)arylation. Utilizing a newly synthesized halogenated monomer, dibromopyrrolo[3,2-b]pyrrole (Br2DPP), that is synthesized in a one-step process with nontoxic starting materials, this research will describe the copolymerization of DPP with thienopyrroledione (TPD). The synthesis is accomplished using an environmentally benign/sustainable polymerization process known as direct (hetero)arylation polymerization, while utilizing various sustainable solvents, such as 2-MeTHF. DHAP also will be used to produce the same polymer with both toluene, THF, and cyclopentyl methylether in order to determine the feasibility of using green solvents instead of nonrenewable solvents. Characterization of these polymers will show their molecular weights through gel-permeation chromatography (GPC), optical properties through both UV-Vis and fluorescence spectroscopies, and coupling defects through proton nuclear magnetic resonance (1H NMR) spectroscopy to validate the use of green solvents. Through this process, we will demonstrate that conjugated polymers can be synthesized using sustainable solvents, revolutionizing how conjugated polymers are synthesized and decreasing the environmental footprint left by the production of conjugated polymers.