Study on Intrinsic Stretchability of Diketopyrrolopyrrole-Based π-Conjugated Copolymers with Poly(acryl amide) Side Chains for Organic Field-Effect Transistors
- 15 June 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in ACS Applied Materials & Interfaces
- Vol. 12 (29), 33014-33027
- https://doi.org/10.1021/acsami.0c07496
Abstract
The development of a π-conjugated polymer with hydrogen-bonding moieties has aroused great attention because of the improved molecular stacking and the hydrogen-bonding network. In this study, PDPPTVT (diketopyrrolopyrrole-thiophenevinylenethiophene) and PDPPSe (diketopyrrolopyrrole-selenophene) alkylated with a carbosilane (SiC8) side chain and poly(acryl amide) (PAM)-incorporated alkyl side chain were prepared, and their structure–performance and structure–stretchability correlation were evaluated. By incorporating the DPPTVT backbone and 0, 5, 10, or 20% PAM-incorporated alkyl side chain, the μh value could reach 2.0, 0.97, 0.74, and 0.42 cm2 V–1 s–1, respectively (P1 to P4). The polymer with the PDPPSe backbone and 5% PAM-incorporated alkyl side-chain (P5) exhibited the maximum μh value of 0.96 cm2 V–1 s–1. By extending the PAM moiety from the backbone with alkyl spacers, the solid-state packing and edge-on orientation can be properly maintained. Surprisingly, the PAM-incorporated alkyl side-chain can provide a hydrogen-bonding network serving as sacrificial bonding to mechanical deformation. Therefore, the relevant changes in the crystallographic parameters including the crystalline size and the in-plane π–π stacking distance with a 100% external strain were less than 4 and 0.8%, respectively, from P1 to P3. Therefore, P3 achieved an excellent stretchability while maintaining its molecular orientation and charge-transporting performance. Even with 100% external strain, P3 still provided an orthogonal μh over 0.1 cm2 V–1 s–1. Moreover, by substituting the TVT moiety with the Se moiety, the ductility of the backbone can be further increased when the elastic modulus decreases from 0.80 to 0.36 GPa for P2 to P5. The achieved high μh retention is over 20% after 500 stretching–releasing cycles with a 60% external strain perpendicular to the channel direction for the polymer composed of PDPPSe and 5% PAM content. The results manifest that our newly designed DPP with the PAM-incorporated alkyl side chain provides a promising approach to promote the intrinsic stretchability of the π-conjugated polymers.Keywords
Funding Information
- Ministry of Education (108L9006)
- Ministry of Education, Culture, Sports, Science and Technology (19K22211)
- Ministry of Science and Technology, Taiwan (MOST 108-3017-F-002-002)
- Tokuyama Science Foundation
This publication has 55 references indexed in Scilit:
- A Pseudo‐Regular Alternating Conjugated Copolymer Using an Asymmetric Monomer: A High‐Mobility Organic Transistor in Nonchlorinated SolventsAdvanced Materials, 2015
- Investigation of Structure–Property Relationships in Diketopyrrolopyrrole-Based Polymer Semiconductors via Side-Chain EngineeringChemistry of Materials, 2015
- Oligo(ethylene glycol)-incorporated hybrid linear alkyl side chains for n-channel polymer semiconductors and their effect on the thin-film crystalline structureChemical Communications, 2014
- ε‐Branched Flexible Side Chain Substituted Diketopyrrolopyrrole‐Containing Polymers Designed for High Hole and Electron MobilitiesAdvanced Functional Materials, 2014
- H- and J-Aggregate Behavior in Polymeric SemiconductorsAnnual Review of Physical Chemistry, 2014
- Silver Nanowire Percolation Network Soldered with Graphene Oxide at Room Temperature and Its Application for Fully Stretchable Polymer Light-Emitting DiodesACS Nano, 2014
- Side Chain Engineering in Solution-Processable Conjugated PolymersChemistry of Materials, 2013
- Solution-Processable Ambipolar Diketopyrrolopyrrole–Selenophene Polymer with Unprecedentedly High Hole and Electron MobilitiesJournal of the American Chemical Society, 2012
- Precise syntheses of chain-multi-functionalized polymers, star-branched polymers, star-linear block polymers, densely branched polymers, and dendritic branched polymers based on iterative approach using functionalized 1,1-diphenylethylene derivativesProgress in Polymer Science, 2005
- Anionic Synthesis of Well-Defined Poly(m-halomethylstyrene)s and Branched Polymers via Graft-onto MethodologyMacromolecules, 2000