Synthesis and Optoelectronic Properties of New Methoxy-Substituted Diketopyrrolopyrrole Polymers

• Published in: ACS omega 2019-05, Vol.4 (5), p.9427-9433
• Main Authors: Domokos, Andras, Aronow, Sean D, Tang, Teresa, Shevchenko, Nikolay E, Tantillo, Dean J, Dudnik, Alexander S
• Format: Article
• Language: English
• ISSN: 2470-1343; 2470-1343
• DOI: 10.1021/acsomega.9b01125

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.