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Functional Transformation of Four-Bladed Rylene Propellers Utilizing Non-Metal and d <sup>8</sup> Metal Core Shifting Strategy: Significant Impact on Photovoltaic Performance and Electrocatalytic Hydrogen Evolution Activity
摘要： Two kinds of four-bladed perylene diimide (PDI) propellers with d8 metal and non-metal cores are efficiently synthesized. The Ni-PDI, Pd-PDI, and Pt-PDI propellers, equipped with d8 metal cores, have two absorption bands at 350-650 nm and 780-1200 nm with deep LUMO levels of -4.40 eV to -4.51 eV. The TTF-PDI, QU-PDI, and PH-PDI propellers with non-metal cores have only one absorption band at 350-650 nm with upshifted LUMO levels. Interestingly, the organic photovoltaic (OPV) results show that reducing the intramolecular charge traps between the blade and core subunits of the PDI propellers can effectively improve the power conversion efficiency (PCE). The device based on the QU-PDI acceptor exhibits a PCE that is up to more than 300 times higher (9.33%) than that of the d8 metal core PDI propellers (Pd-PDI, PCE=0.03%), which is one of the best photovoltaic performances with an excellent fill factor (FF=71.8%) exhibited by PDI-derivative acceptors. Conversely, the electro-catalytic H2 evolution activity of Pt-PDI (current destiny =10.00 mA/cm2 at -0.377 V), which exhibited a record performance for PDI-based catalysts to date, is up to 1000 times greater than that of the non-metal core PDI propellers (QU-PDI, 0.01 mA/cm2 at -0.377 V). Our results indicate that both highly efficient OPV and electrochemical H2 evolution catalysts can be achieved via the rational functionalization of PDI propellers with non-metal and d8 metal cores.
关键词： d8 metal cores,electrocatalytic hydrogen evolution,non-metal cores,organic photovoltaic (OPV),perylene diimide (PDI)
更新于2025-09-16 10:30:52
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Construction of Effective Polymer Solar Cell Using 1,7-Disubstituted Perylene Diimide Derivatives as Electron Transport Layer
摘要： The poor compatibility of an inorganic electron transport layer with the active layer and an ultrathin film organic material becomes a great obstacle in producing high-quality polymer solar cells with high-throughput roll-to-roll (R2R) method. Novel effective polymer solar cells had been fabricated by introducing 1, 7-disubstituted perylene diimide derivatives PDIH, PDIC, and PDIN as an electron transporting layer. It was noteworthy that PDIN could obviously improve the power conversion efficiency of solar cells that incorporated a photoactive layer composed of poly[(3-hexylthiophene)-2, 5-diyl] (P3HT) and the fullerene acceptor [6, 6-phenyl-C71-butyric acid methyl ester] (PC71BM). The power conversion efficiency varies from 1.5% for ZnO transparent cathode-based solar cells to 2.1% for PDIN-based electron transport layer-free solar cells. This improved performance could be attributed to the following reasons: the interaction between N atom in PDIN and O atom in indium tin oxide (ITO) reduced the work function of ITO, increased the built-in electric field, and thus lowered the electron transport barrier and improved the electron extraction ability of cathode, the appropriate roughness of the active layer increased the contact area with anode interfacial layer and enhanced the hole transport efficiency. These experimental results revealed that PDIN can be a promising novel effective material with a simplified synthesis process and lower cost as an electron transporting layer.
关键词： polymer solar cells,electron transport layer,perylene diimide derivatives,indium tin oxide,power conversion efficiency
更新于2025-09-12 10:27:22
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Interlayer Engineering of Flexible and Large-Area Red Organic-Light-Emitting Diodes Based on an N-Annulated Perylene Diimide Dimer
摘要： Flexible red OLEDs based on a quadruple-layer stack, in between electrodes, with 160 mm2 active area were fabricated in ambient air on PET via slot-die-coating. For the OLED structure PET/ITO/PEDOT:PSS/PVK/PFO:tPDI2N-EH/ZnO/Ag, the ink formulations and coating parameters for each layer were systematically evaluated and optimized. The air-stable red-light-emitting material tPDI2N-EH was successfully utilized as blended homogeneous film with PFO for the emitting layer. The use of an organic hole-transport layer (PVK) and inorganic electron injection layer (ZnO) significantly improved the brightness of the reference device from 4 to 303 cd/m2. Surface analysis using AFM measurements showed that the PVK interlayer reduced the surface roughness of the hole injection layer (PEDOT:PSS) from 0.45 to 0.17 nm, which improved the ability to form uniform emitting layers on top. In addition, the ZnO interlayer decreased surface roughness from 1.26 to 0.85 nm and reduced the turn-on voltage of the device from 5.0 to 2.8 V.
关键词： perylene diimide,slot-die-coating,solution-processed,flexible substrate,large-area,OLED
更新于2025-09-12 10:27:22
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Perylene Diimide based Organic Photovoltaics with Slot-Die Coated Active Layers from Halogen-Free Solvents in Air at Room Temperature
摘要： Herein, we investigate the role of processing solvent additives on the formation of polymer-perylene diimide bulk-heterojunction active layers for organic photovoltaics using both spin-coating and slot-die coating methods. We compare the effect of 1,8-diiodooctane (DIO) and diphenyl ether (DPE) as solvent additives on the aggregation behavior of the non-fullerene acceptor tPDI2N-EH in neat films and blended films with the benzodithiophene-quinoxaline (BDT-QX, QX-3) donor polymer, processed from toluene in air. DIO-processing crystallizes the tPDI2N-EH acceptor and leads to decreased solar cell performance. DPE-processing has a more subtle effect on the bulk-heterojunction morphology and leads to improved solar cell performance. Comparing spin vs. slot-die coating methods, the effect of DPE is prominent for slot-die coated active layers. While similar device power conversion efficiencies are achieved with active layers coated with both methods (ca. 7.3% vs. 6.5%), the use of DPE improves film quality when the slot-die coating method is employed.
关键词： Organic photovoltaics,Halogen-free processing,Perylene diimide,Slot-die coating,Solvent additive,Diphenyl ether,Quinoxaline,Morphology control
更新于2025-09-12 10:27:22
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Diketopyrrolopyrrole/perylene-diimide and thiophene based D-π-A low bandgap polymer sensitizers for application in dye sensitized solar cells
摘要： In this study, diketopyrrolopyrrole-alt-thiophene (P1 and P2) and perylene-diimide-alt-thiophene (P3 and P4) based donor-π-acceptor (D-π-A) copolymers have been synthesized from the corresponding monomers through Pd-catalyzed Sonogashira polymerization protocol. The well defined and soluble π-conjugated copolymers having alkyl and fluoroalkyl substituents (P1-P4) have been characterized by multinuclear NMR spectra as well as by tetradetector GPC studies showing molecular weight (Mn) in the range of 18-20 kDa with good polydispersity indices of 1.31-1.48. The donor-acceptor based copolymers absorb broadly throughout the visible region. Notably, perylene diimide-thiophene based copolymers (P3 and P4) exhibits an absorption onset at ca. 800 nm corresponding to a bandgap of 1.63 and 1.61 eV (Egopt). DFT computational studies of the model π-conjugated units have also been investigated to understand the molecular geometries and electronic properties of the polymeric unit. The synthesized D-π-A polymers have been utilized as active materials for polymer-sensitized solar cells (PSSCs). The copolymers are effectively adsorbed onto the surface of nanostructured TiO2 photoanode as a result of facile interaction of the anchored -C=O units with the metal oxide surface. The spectral profile of the polymer films on mesoporous oxide surface approximately similar to the solution absorption spectra of the polymer. Interestingly, the polymers featuring perylene diimide unit (P3 and P4) exhibit promising power conversion efficiency (PCE) of 2.71 and 2.96% with a short circuit current (JSC) of 7.54 and 7.85 mA·cm-2 respectively, and IPCE of 42-45% under 1.5 AM illumination.
关键词： Dye Sensitized Solar Cells,Polymer Sensitizers,Thiophene,Perylene-diimide,Diketopyrrolopyrrole,Low Bandgap,D-π-A
更新于2025-09-12 10:27:22
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Perylene Diimide‐Based Nonfullerene Polymer Solar Cells with over 11% Efficiency Fabricated by Smart Molecular Design and Supramolecular Morphology Optimization
摘要： A series of perylene diimide (PDI) derivatives, TPP-PDI, TPO-PDI, and TPS-PDI, are developed for nonfullerene polymer solar cells (NF-PSCs) by flaking three PDI skeletons around 3D central cores with different configurations and electronic states, such as triphenylphosphine (TPP), triphenylphosphine monoxide (TPO), and triphenylphosphine sulfide (TPS). These small-molecule acceptors have a “three-wing propeller” structure due to their similar backbones. By changing the electron density of phosphorus atoms through oxidation and sulfuration, the “folding-back” strength is decreased, resulting in a less twisted molecular conformation. The stronger electron-withdrawing ability of the oxygen atom affords TPO-PDI the least twisted conformation, which enhances the crystallinity of this complex. NF-PSCs based on PTTEA:TPO-PDI exhibit a high power conversion efficiency (PCE) of 8.65%. Ultimately, the joint “molecular lock” effect arising from OH???F and OH???OP supramolecular interactions is achieved by introducing 4,4′-biphenol as an additive, which successfully promotes fibril-like phase separation and blend morphology optimization to generate the highest PCE of 11.01%, which is currently the highest value recorded for NF-PSCs based on PDI acceptors.
关键词： triphenylphosphine oxide cores,nonfullerene polymer solar cells,molecular locks,hydrogen bonds,perylene diimide acceptors
更新于2025-09-11 14:15:04
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Fusion or non-fusion of quasi-two-dimensional fused perylene diimide acceptors: the importance of molecular geometry for fullerene-free organic solar cells
摘要： In this work, two small molecular electron acceptor (BT-FPDI and fBT-FPDI) comprising a central bithiophene (BT) bridge and two fused perylene diimide (FPDI) units were designed and synthesized for fullerene-free organic solar cells (OSCs). The molecular geometry of these electron acceptors can be adjusted through a locked conformation via photocyclization reaction. As expected, BT-FPDI has a highly twisted geometry with the assistance of the quasi-two-dimensional (quasi-2D) configuration of FPDI unit and modest dihedral angles between FPDI and BT units, while fBT-FPDI shows a relatively planar geometry with symmetrically aligned the FPDI wings. When pairing with polymer donor PTB7-Th, the intrinsic configuration characteristic of BT-FPDI guaranteed an impressive power conversion efficiency (PCE) of 8.07% with an open circuit voltage (Voc) of 0.81 V, and a recorded high short-circuit current density (Jsc) of 17.35 mA/cm2, which is almost the highest Jsc value reported in PDI-based fullerene-free OSCs. However, the optimal device employing fBT-FPDI as electron acceptor only delivered a PCE of 5.89% with a significantly reduced Jsc of 12.30 mA/cm2. The interesting result show that, unlike traditional PDI molecules, the ring-fusion molecular design has not produce the desired positive effect in FPDI derivatives, and also provide a new insight into the regulation of the molecular geometry based on FPDI acceptors with intrinsic quasi-2D structure.
关键词： perylene diimide,molecular geometry,fullerene-free organic solar cells,ring-fusion,power conversion efficiency
更新于2025-09-11 14:15:04
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Propeller-like acceptors with difluoride perylene diimides for organic solar cells
摘要： Perylene diimide (PDI) is one of most intensively studied non-fullerene small molecule acceptors (SMAs). By fluorination on the conjugated backbone, a new PDI with difluoride substitution on adjacent bay positions of PDI is prepared. Then, four propeller-like SMAs are obtained by linking four PDIs with an aromatic core, wherein the molecular geometry is modulated by ring fusion of the aromatic core. Further study reveals that fluorination is helpful to enhance the absorption intensity, and thus promote the current density in organic solar cells. In addition, the ring-fused strategy is able to suppress the distortion and rotation of relevant molecules. Therefore, these four acceptors exhibit significantly diversity of photovoltaic performance, wherein the acceptor FPDIF4-DTC consisting of a fused core and fluoro-substituted PDIs shows a best efficiency of 5.1%. This result implies that fluorination on PDI conjugated backbone is a successful way to construct promising SMAs.
关键词： Perylene Diimide,Fluorination,Non-fullerene acceptor,Organic solar cells
更新于2025-09-11 14:15:04
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Perylene diimide based star-shaped small molecular acceptors for high efficiency organic solar cells
摘要： We designed and synthesized three PDI derivatives (PDI-II, PDI-III and PDI-IV). All these acceptor molecules have a central benzene core and the PDI units are linked to the central benzene core by an acetylene spacer. PDI-II is a linear molecule, which bears two flanked PDI units, PDI-III is a c3-symmetrical star-shaped molecule with three peripheral PDI units, and PDI-IV is a star-shaped molecule with four PDI units linked to the 1,2,4,5-positions of the central benzene core. These absorption features indicated that the PDI units in PDI-II and PDI-III are planar, whereas the PDI units in PDI-IV are twisted due to the steric crowding. Compared with the linear PDI-II, the star-shape could e?ectively prevent PDI-III and PDI-IV from forming large aggregates when blended with the donor polymer PBDB-T. PBDB-T:PDI-II, PBDB-T:PDI-III and PBDB-T:PDI-IV based OSCs gave power conversion e?ciencies (PCEs) of 3.05%, 6.00% and 1.04%, respectively. The big di?erences in electron mobility and PCE for PDI-III and PDI-IV are probably due to the fact that the PDI units in PDI-III are planar and those in PDI-IV are twisted.
关键词： Perylene diimide,power conversion efficiencies,star-shaped small molecular acceptors,organic solar cells
更新于2025-09-11 14:15:04
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Discrete Dimers of Redox-Active and Fluorescent Perylene Diimide-Based Rigid Isosceles Triangles in the Solid State
摘要： The development of rigid covalent chiroptical organic materials, with multiple, readily available redox states, which exhibit high photoluminescence is of particular importance in relation to both organic electronics and photonics. The chemically stable, thermally robust and redox-active perylene diimide (PDI) fluorophores have received ever-increasing attention owing to their excellent fluorescence quantum yields in solution. Planar PDI derivatives, however, generally suffer from aggregation-caused emission quenching in the solid state. Herein, we report on the design and synthesis of two chiral isosceles triangles wherein one PDI fluorophore and two pyromellitic diimide (PMDI) or naphthalene diimide (NDI) units are arranged in a rigid cyclic triangular geometry. The optical, electronic and magnetic properties of the rigid isosceles triangles are fully characterized by a combination of optical spectroscopies, X-ray diffraction, cyclic voltammetry, and computational modeling techniques. Single-crystal X-ray diffraction analysis shows that both isosceles triangles form discrete, nearly cofacial PDI-PDI π-dimers in the solid state. While the triangles exhibit fluorescence quantum yields of almost unity in solution, the dimers in the solid state exhibit very weak — yet at least an order of magnitude higher — excimer fluorescence yield in comparison with the almost completely quenched fluorescence of a reference PDI. The triangle containing both NDI and PDI subunits shows superior intramolecular energy transfer from the lowest excited singlet state of the NDI to that of the PDI subunit. Cyclic voltammetry suggests that both isosceles triangles exhibit multiple, easily accessible and reversible redox states. Applications beckon in arenas related to molecular optoelectronic devices.
关键词： intramolecular energy transfer,isosceles triangles,rigid covalent chiroptical organic materials,naphthalene diimide,excimer fluorescence,redox-active,π-dimers,photoluminescence,perylene diimide,pyromellitic diimide,cyclic voltammetry
更新于2025-09-04 15:30:14