Document Type

Article

Publication Date

Spring 2020

Faculty Sponsor

Dr. Ted Pappenfus

Abstract

Indophenine, a deep blue dye and a quinoidal compound, has shown potential as a monomer in donor-acceptor copolymer formation for use in energy and device applications. Despite the barrier of low solubility, we previously polymerized an indophenine-based monomer IQ to form PolyIQ-co-thiophene (PIQ) in a 95% yield using Stille coupling. Although PIQ has desirable electronic properties, Stille coupling is a particularly unsustainable method. In contrast, direct arylation polymerization (DArP) is a more sustainable polymerization method that reduces synthetic steps and toxic byproducts. Therefore, we now report the DArP of IQ to form PolyIQ-co-ProDOT (ProPIQ) in a 96% yield. ProPIQ boasts a low polydispersity index of 1.13 and a molecular weight of 6047 g/mol, indicating the formation of low-mass but uniform polymers. Spectroscopic analysis of ProPIQ in solution and film indicate an absorption of 800-850 nm, approaching the near-IR range. Additionally, ProPIQ has a low band-gap of 1.2 eV, suggesting potential for use in solar cell and device applications. Although optimization attempts to further enhance the solubility of ProPIQ are incomplete, the high yield and desirable electronic properties of ProPIQ demonstrate that DArP is an effective route toward indophenine-based polymers.

Comments

This research was done through the Undergraduate Research Opportunities Program (UROP).

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