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High-performing n-type polymers are crucial for the advance of organic electronics field, however strong electron-deficient building blocks with optimized physicochemical properties for constructing them are still limited. The imide-functionalized polycyclic aromatic hydrocarbons (PAHs) with extended π-conjugated framework, high electron deficiency and good solubility serve as promising candidates for developing high-performance n-type polymers. Among the PAHs, phenanthrene (PhA) features a well-delocalized aromatic π-system with multiple modifiable active sites . However, the PhA-based imides are seldom studied, mainly attributed to the synthetic challenge. Herein, we report two functionalized PhAs, CPOI and CPCNI, by simultaneously incorporating imide with carbonyl or dicyanomethylene onto PhA. Notably, the dicyanomethylene-modified CPCNI exhibits a well stabilized LUMO energy level (-3.84 eV), attributed to the synergetic inductive effect from imide and cyano groups. Subsequently, based on CPOI and CPCNI, two polymers PCPOI-Tz and PCPCNI-Tz were developed. Applied to organic thin-film transistors, owing to the strong electron-deficiency of CPCNI, polymer PCPCNI-Tz shows an improved electron mobility and largely decreased threshold voltage compared with PCPOI-Tz. This work affords two structurally novel electron-deficient building blocks and highlights the effectiveness of dual functionalization of PhAs with strong electron-withdrawing groups for devising n-type polymers.
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http://dx.doi.org/10.1002/anie.202319627 | DOI Listing |
Adv Mater
December 2024
State Key Laboratory of Polymer Physics and Chemistry & Key Laboratory of Polymer Science and Technology, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. China.
The charge transport of channel materials in n-type organic electrochemical transistors (OECTs) is greatly limited by the adverse effects of electrochemical doping, posing a long-standing puzzle for the community. Herein, an n-type conjugated polymer with glycolated side chains (n-PT3) is introduced. This polymer can adapt to electrochemical doping and create more organized nanostructures, mitigating the adverse effects of electrochemical doping.
View Article and Find Full Text PDFSmall
December 2024
Tissue Electronics, Istituto Italiano di Tecnologia, Naples, 80125, Italy.
The integration of organic electronic materials with biological systems to monitor, interface with, and regulate physiological processes is a key area in the field of bioelectronics. Central to this advancement is the development of cell-chip coupling, where materials engineering plays a critical role in enhancing biointerfacing capabilities. Conductive polymers have proven particularly useful in cell interfacing applications due to their favorable biophysical and chemical properties.
View Article and Find Full Text PDFAdv Mater
December 2024
Organic Bioelectronics Laboratory, Biological and Environmental Science and Engineering Division, King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Saudi Arabia.
N-type organic mixed ionic electronic conductors (n-OMIECs) struggle to match the performance of p-type counterparts, particularly in bioelectronics' flagship device, the organic electrochemical transistor. Enhancing n-type transistor performance typically necessitates the synthesis of new materials. More sustainable post-synthetic treatments, known to improve organic devices in dry and oxygen-free conditions, are not applied to n-OMIECs.
View Article and Find Full Text PDFJ Phys Chem Lett
December 2024
Department of Materials Science and Engineering, School of Molecular Science and Engineering, Vidyasirimedhi Institute of Science and Technology (VISTEC), Rayong 21210, Thailand.
Nickel bis(dithiolene) complexes are promising candidates for novel n-type semiconductors, which are air-stable and highly conductive. A key issue for further development is that their synthesis often yields undesired products, greatly limiting the degree of polymerization as well as purity and adversely affecting their electronic properties. Crucially, there is a lack of in-depth identification of these species and understanding of the reaction mechanism.
View Article and Find Full Text PDFJACS Au
November 2024
Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, School of Materials Science and Engineering, Peking University, Beijing 100871, China.
Polymer thermoelectrics (TEs) have attracted increasing interest in recent years, owing to their great potential in intimate integration with wearable electronics for powering small electronics/sensors and personal temperature regulation. Over the past few decades, substantial progress has been made in enhancing polymer TE performance. However, the electrical conductivity and power factor of most n-doped polymers are about an order of magnitude lower than those of their p-type counterparts, impeding the development of highly efficient polymer TE devices.
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