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Synthesis and Optoelectronic Properties of New Methoxy-Substituted Diketopyrrolopyrrole Polymers.

ABSTRACT: The introduction of functional groups with varying electron-donating/-withdrawing properties at the ?-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 ?-position in an effort to modulate polymer properties. Homopolymers and co-polymers of the new ?-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 ?-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 ?-methoxy polymers.

SUBMITTER: Domokos A

PROVIDER: S-EPMC6648756 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Synthesis and Optoelectronic Properties of New Methoxy-Substituted Diketopyrrolopyrrole Polymers.

Domokos Andras A Aronow Sean D SD Tang Teresa T Shevchenko Nikolay E NE Tantillo Dean J DJ Dudnik Alexander S AS

ACS omega 20190530 5

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 wer ...[more]

PMID: 31460033

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Project description:Diketopyrrolopyrroles (DPP) have been recognized as a promising acceptor unit for construction of semiconducting donor-acceptor (D-A) polymers, which are typically flanked by spacers such as thiophene rings via a carbon-carbon single bond formation. It may suffer from a decrease in the coplanarity of the molecules especially when bulky side chains are installed. In this work, the two N atoms in the DPP unit are further fused with C-3 of the two flanking thiophene rings, yielding a π-expanded, very planar fused-ring building block (DPPFu). A novel DPPFu-based D-A copolymer (PBDTT-DPPFu) was successfully synthesized, consisting of a benzo[1,2-b:4,5-b']dithiophene (BDTT) unit as a donor and a DPPFu unit as an acceptor. For comparison, the unfused DPP-based counterpart PBDTT-DPP was also synthesized. Two dodecyl alkyl chains were attached to thiophene rings of DPP moieties to ensure good solubility of the DPPFu-based polymer. The influence of the ring-fusion effect on their structure, photophysical properties, electronic properties, molecular packing, and charge transport properties is investigated. Ring-fusion enhances the intermolecular interactions of PBDTT-DPPFu polymer chains as indicated by density functional theory calculation and analysis of electrostatic potential and van der Waals potential and results in significantly improved molecular packing for both the in-plane and out-of-plane directions as suggested by X-ray measurements. Finally, we correlate the molecular packing to the device performance by fabricating field-effect transistors based on these two polymers. The charge carrier mobility of the ring-fused polymer PBDTT-DPPFu is significantly higher as compared to the PBDTT-DPP polymer without ring-fusion, although PBDTT-DPPFu exhibited a much lower number-average molecular weight of 17 kDa as compared to PBDTT-DPP with a molecular weight of 108 kDa. The results from our comparative study provide a robust way to increase the interchain interaction by ring-fusion-promoted coplanarity.

Dataset Information

Synthesis and Optoelectronic Properties of New Methoxy-Substituted Diketopyrrolopyrrole Polymers.

Publications

Synthesis and Optoelectronic Properties of New Methoxy-Substituted Diketopyrrolopyrrole Polymers.

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