| 1. |
- Li, Wei, et al.
(författare)
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One-Step Synthesis of Precursor Oligomers for Organic Photovoltaics: A Comparative Study between Polymers and Small Molecules
- 2015
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Ingår i: ACS Applied Materials and Interfaces. - : American Chemical Society (ACS). - 1944-8244 .- 1944-8252. ; 7:49, s. 27106-27114
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Tidskriftsartikel (refereegranskat)abstract
- Two series of oligomers TQ and rhodanine end-capped TQ-DR were synthesized using a facile one-step method. Their optical, electrical, and thermal properties and photovoltaic performances were systematically investigated and compared. The TQ series of oligomers were found to be amorphous, whereas the TQ-DR series are semicrystalline. For the TQ oligomers, the results obtained in solar cells show that as the chain length of the oligomers increases, an increase in power conversion efficiency (PCE) is obtained. However, when introducing 3-ethylrhodanine into the TQ oligomers as end groups, the PCE of the TQ-DR series of oligomers decreases as the chain length increases. Moreover, the TQ-DR series of oligomers give much higher performances compared to the original amorphous TQ series of oligomers owing to the improved extinction coefficient (epsilon) and crystallinity afforded by the rhodanine. In particular, the highly crystalline oligomer TQ5-DR, which has the shortest conjugation length shows a high hole mobility of 0.034 cm(2) V-1 s(-1) and a high PCE of 3.14%, which is the highest efficiency out of all of the six oligomers. The structure-property correlations for all of the oligomers and the TQ1 polymer demonstrate that structural control of enhanced intermolecular interactions and crystallinity is a key for small molecules/oligomers to achieve high mobilities, which is an essential requirement for use in OPVs.
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| 2. |
- James, David, 1987, et al.
(författare)
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High-Performance Hole Transport and Quasi-Balanced Ambipolar OFETs Based on D–A–A Thieno-benzo-isoindigo Polymers
- 2016
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Ingår i: Advanced Electronic Materials. - : Wiley. - 2199-160X. ; 2:4
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Tidskriftsartikel (refereegranskat)abstract
- Two new conjugated polymers are synthesized based on a novel donor–acceptor–acceptor (D–A–A) design strategy with the intention of attaining lower lowest unoccupied molecular obital levels compared to the normally used D–A strategy. By coupling two thieno-benzo-isoindigo units together via the phenyl position to give a new symmetric benzene-coupled di-thieno-benzo-isoindigo (BdiTBI) monomer as an A–A acceptor and thiophene (T) or bithiophene (2T) as a donor, two new polymers PT-BdiTBI and P2T-BdiTBI are synthesized via Stille coupling. The two polymers are tested in top gate and top contact field effect transistors, which exhibit balanced ambipolar charge transport properties with poly(methyl methacrylate) as dielectric and a high hole mobility up to 1.1 cm2 V–1 s–1 with poly(trifluoroethylene) as dielectric. The polymer films are investigated using atomic force microscopy, which shows fibrous features due to their high crystallinity as indicated by grazing incidence wide-angle X-ray scattering. The theoretical calculations agree well with the experimental data on the energy levels. It is demonstrated that the D–A–A strategy is very effective for designing low band gap polymers for organic electronic applications.
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| 3. |
- Riera-Galindo, Sergi, et al.
(författare)
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Impact of Singly Occupied Molecular Orbital Energy on the n-Doping Efficiency of Benzimidazole Derivatives
- 2019
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Ingår i: ACS Applied Materials and Interfaces. - : AMER CHEMICAL SOC. - 1944-8244 .- 1944-8252. ; 11:41, s. 37981-37990
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Tidskriftsartikel (refereegranskat)abstract
- We investigated the impact of singly occupied molecular orbital (SOMO) energy on the n-doping efficiency of benzimidazole derivatives. By designing and synthesizing a series of new air-stable benzimidazole-based dopants with different SOMO energy levels, we demonstrated that an increase of the dopant SOMO energy by only similar to 0.3 eV enhances the electrical conductivity of a benchmark electron-transporting naphthalenediimide-bithiophene polymer by more than 1 order of magnitude. By combining electrical, X-ray diffraction, and electron paramagnetic resonance measurements with density functional theory calculations and analytical transport simulations, we quantitatively characterized the conductivity, Seebeck coefficient, spin density, and crystallinity of the doped polymer as a function of the dopant SOMO energy. Our findings strongly indicate that charge and energy transport are dominated by the (relative) position of the SOMO level, whereas morphological differences appear to play a lesser role. These results set molecular-design guidelines for next-generation n-type dopants.
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| 4. |
- Wang, Suhao, et al.
(författare)
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A Chemically Doped Naphthalenediimide-Bithiazole Polymer for n-Type Organic Thermoelectrics
- 2018
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Ingår i: Advanced Materials. - : WILEY-V C H VERLAG GMBH. - 0935-9648 .- 1521-4095. ; 30:31
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Tidskriftsartikel (refereegranskat)abstract
- The synthesis of a novel naphthalenediimide (NDI)-bithiazole (Tz2)-based polymer [P(NDI2OD-Tz2)] is reported, and structural, thin-film morphological, as well as charge transport and thermoelectric properties are compared to the parent and widely investigated NDI-bithiophene (T2) polymer [P(NDI2OD-T2)]. Since the steric repulsions in Tz2 are far lower than in T2, P(NDI2OD-Tz2) exhibits a more planar and rigid backbone, enhancing p-p chain stacking and intermolecular interactions. In addition, the electron-deficient nature of Tz2 enhances the polymer electron affinity, thus reducing the polymer donor-acceptor character. When n-doped with amines, P(NDI2OD-Tz2) achieves electrical conductivity (approximate to 0.1 S cm(-1)) and a power factor (1.5 mu W m(-1) K-2) far greater than those of P(NDI2OD-T2) (0.003 S cm(-1) and 0.012 mu W m(-1) K-2, respectively). These results demonstrate that planarized NDI-based polymers with reduced donor-acceptor character can achieve substantial electrical conductivity and thermoelectric response.
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| 5. |
- Wang, Suhao, et al.
(författare)
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Sequential Doping of Ladder-Type Conjugated Polymers for Thermally Stable n-Type Organic Conductors
- 2020
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Ingår i: ACS Applied Materials & Interfaces. - : American Chemical Society (ACS). - 1944-8252 .- 1944-8244. ; 12:47, s. 53003-53011
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Tidskriftsartikel (refereegranskat)abstract
- Doping of organic semiconductors is a powerful tool to optimize the performance of various organic (opto)electronic and bioelectronic devices. Despite recent advances, the low thermal stability of the electronic properties of doped polymers still represents a significant obstacle to implementing these materials into practical applications. Hence, the development of conducting doped polymers with excellent long-term stability at elevated temperatures is highly desirable. Here, we report on the sequential doping of the ladder-type polymer poly(benzimidazobenzophenanthroline) (BBL) with a benzimidazole-based dopant (i.e., N-DMBI). By combining electrical, UV-vis/infrared, X-ray diffraction, and electron paramagnetic resonance measurements, we quantitatively characterized the conductivity, Seebeck coefficient, spin density, and microstructure of the sequentially doped polymer films as a function of the thermal annealing temperature. Importantly, we observed that the electrical conductivity of N-DMBI-doped BBL remains unchanged even after 20 h of heating at 190 °C. This finding is remarkable and of particular interest for organic thermoelectrics.
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| 6. |
- Zhuang, Wenliu, 1979, et al.
(författare)
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Synthesis and Electronic Properties of Diketopyrrolopyrrole-Based Polymers with and without Ring-Fusion
- 2021
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Ingår i: Macromolecules. - : American Chemical Society (ACS). - 0024-9297 .- 1520-5835. ; 54:2, s. 970-980
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Tidskriftsartikel (refereegranskat)abstract
- 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 p-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.
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| 7. |
- Alsufyani, Maryam, et al.
(författare)
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The effect of aromatic ring size in electron deficient semiconducting polymers for n-type organic thermoelectrics
- 2020
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Ingår i: Journal of Materials Chemistry C. - : ROYAL SOC CHEMISTRY. - 2050-7526 .- 2050-7534. ; 8:43, s. 15150-15157
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Tidskriftsartikel (refereegranskat)abstract
- N-type semiconducting polymers have been recently utilized in thermoelectric devices, however they have typically exhibited low electrical conductivities and poor device stability, in contrast to p-type semiconductors, which have been much higher performing. This is due in particular to the n-type semiconductors low doping efficiency, and poor charge carrier mobility. Strategies to enhance the thermoelectric performance of n-type materials include optimizing the electron affinity (EA) with respect to the dopant to improve the doping process and increasing the charge carrier mobility through enhanced molecular packing. Here, we report the design, synthesis and characterization of fused electron-deficient n-type copolymers incorporating the electron withdrawing lactone unit along the backbone. The polymers were synthesized using metal-free aldol condensation conditions to explore the effect of enlarging the central phenyl ring to a naphthalene ring, on the electrical conductivity. When n-doped with N-DMBI, electrical conductivities of up to 0.28 S cm(-1), Seebeck coefficients of -75 mu V K-1 and maximum Power factors of 0.16 mu W m(-1) K-2 were observed from the polymer with the largest electron affinity of -4.68 eV. Extending the aromatic ring reduced the electron affinity, due to reducing the density of electron withdrawing groups and subsequently the electrical conductivity reduced by almost two orders of magnitude.
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| 8. |
- Chen, Hu, et al.
(författare)
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Acene Ring Size Optimization in Fused Lactam Polymers Enabling High n-Type Organic Thermoelectric Performance
- 2021
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Ingår i: Journal of the American Chemical Society. - : AMER CHEMICAL SOC. - 0002-7863 .- 1520-5126. ; 143:1, s. 260-268
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Tidskriftsartikel (refereegranskat)abstract
- Three n-type fused lactam semiconducting polymers were synthesized for thermoelectric and transistor applications via a cheap, highly atom-efficient, and nontoxic transition-metal free aldol polycondensation. Energy level analysis of the three polymers demonstrated that reducing the central acene core size from two anthracenes (A-A), to mixed naphthalene-anthracene (A-N), and two naphthalene cores (N-N) resulted in progressively larger electron affinities, thereby suggesting an increasingly more favorable and efficient solution doping process when employing 4-(2,3-dihydro-1,3-dimethyl-1H-benzimidazol-2-yl)-N,N-dimethylbenzenamine (N-DMBI) as the dopant. Meanwhile, organic field effect transistor (OFET) mobility data showed the N-N and A-N polymers to feature the highest charge carrier mobilities, further highlighting the benefits of aryl core contraction to the electronic performance of the materials. Ultimately, the combination of these two factors resulted in N-N, A-N, and A-A to display power factors (PFs) of 3.2 mu W m(-1) K-2, 1.6 mu W m(-1 )K(-2), and 0.3 mu W m(-1) K-2, respectively, when doped with N-DMBI, whereby the PFs recorded for N-N and A-N are among the highest reported in the literature for n-type polymers. Importantly, the results reported in this study highlight that modulating the size of the central acene ring is a highly effective molecular design strategy to optimize the thermoelectric performance of conjugated polymers, thus also providing new insights into the molecular design guidelines for the next generation of high-performance n-type materials for thermoelectric applications.
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| 9. |
- Dongo, Patrice D., et al.
(författare)
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Detection of Ice Formation With the Polymeric Mixed Ionic-Electronic Conductor PEDOT: PSS for Aeronautics
- 2023
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Ingår i: Advanced Electronic Materials. - : WILEY. - 2199-160X.
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Tidskriftsartikel (refereegranskat)abstract
- Ice formation detection is important in telecommunications and aeronautics, e.g., ice on the wings of an aircraft affects its aerodynamic performance and leads to fatal accidents. While many types of sensors exist, resistive sensors for ice detection have been poorly explored. They are however attractive because of their simplicity and the possibility to install an array of sensors on large areas to map the ice formation on wings. Hygroscopic ionic conductors have been demonstrated for resistive ice sensing but their high resistance prevents the readout of sensor arrays. In this work, mixed ionic-electronic polymer conductors (MIEC) are considered for the first time for ice detection. The polymer blend poly(3,4-ethylenedioxythiophene):polystyrene sulfonate (PEDOT:PSS) is solution deposited on a pair of electrodes. The sensor displays an abrupt rise in electrical resistance during the transition phase between water liquid to solid. It is proposed that the morphology and electronic transport in PEDOT are affected by the freezing event because the absorbed water in the PSS-rich phase undergoes dilatation upon forming ice crystals. For the aeronautics application, successful tests of integration of sensing layer in pre-preg layers of aeronautical grade and freezing detection are carried out to validate the ice detection principle.
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| 10. |
- Håkansson, Anna, et al.
(författare)
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Effect of (3-Glycidyloxypropyl)Trimethoxysilane (GOPS) on the Electrical Properties of PEDOT:PSS Films
- 2017
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Ingår i: Journal of Polymer Science Part B. - : WILEY. - 0887-6266 .- 1099-0488. ; 55:10, s. 814-820
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Tidskriftsartikel (refereegranskat)abstract
- Poly(3,4-ethylenedioxythiophene) doped with poly(styrenesulfonate) (PEDOT:PSS) has been reported as a successful functional material in a broad variety of applications. One of the most important advantages of PEDOT:PSS is its water-solubility, which enables simple and environmental friendly manufacturing processes. Unfortunately, this also implies that pristine PEDOT:PSS films are unsuitable for applications in aqueous environments. To reach stability in polar solvents, (3-glycidyloxypropyl)trimethoxysilane (GOPS) is typically used to cross-link PEDOT:PSS. Although this strategy is widely used, its mechanism and effect on PEDOT:PSS performance have not been articulated yet. Here, we present a broad study that provides a better understanding of the effect of GOPS on the electrical and electronic properties of PEDOT:PSS. We show that the GOPS reacts with the sulfonic acid group of the excess PSS, causing a change in the PEDOT:PSS film morphology, while the oxidation level of PEDOT remains unaffected. This is at the origin of the observed conductivity changes. (c) 2017 Wiley Periodicals, Inc.
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