The introduction of functional groups with varying electron-donating/-withdrawing properties at the β-position of diketopyrrolopyrrole (DPP) has been shown to affect the optoelectronic properties of the polymers. We report the synthesis of a new diketopyrrolopyrrole monomer wherein a strong electron-donating substituent, a methoxy group, was incorporated at the β-position in an effort to modulate polymer properties. Homopolymers and co-polymers of the new β-methoxy DPP and nonderivatized DPP were synthesized, and their properties were measured by cyclic voltammetry and UV-vis-near-infrared. Density functional theory computations also were employed to predict the degree of planarity of β-methoxy oligomers to probe the significance of the newly introduced S-O conformational lock. The combined experimental and computational results showed a reduction in the gap between highest occupied molecular orbital/lowest unoccupied molecular orbital levels, a redshift toward the near-infrared region, and an increased planarity in the β-methoxy polymers.
CITATION STYLE
Domokos, A., Aronow, S. D., Tang, T., Shevchenko, N. E., Tantillo, D. J., & Dudnik, A. S. (2019). Synthesis and Optoelectronic Properties of New Methoxy-Substituted Diketopyrrolopyrrole Polymers. ACS Omega, 4(5), 9427–9433. https://doi.org/10.1021/acsomega.9b01125
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