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Fluorinated dithienyl-diketopyrrolopyrrole: a new building block for organic optoelectronic materials
摘要： Diketopyrrolopyrrole (DPP) derivatives have been widely used as the electron-withdrawing unit to construct donor–acceptor (D–A) conjugated systems in organic electronics. The 3,6-position flanking aromatic rings of DPP could strongly influence the optoelectronic properties of DPP-based materials. In this study, a stepwise synthesis strategy was used to prepare monofluorinated and difluorinated dithienyl-DPP. The single crystal of the difluorinated model compound was also obtained. Three polymers based on bithiophene donor and dithienyl-DPP acceptor with different fluorinated positions were synthesized. And preliminary investigations of the influence of fluorination on the optoelectronic properties were performed.
关键词： dithienyl-DPP,Diketopyrrolopyrrole,optoelectronic properties,organic electronics,fluorinated
更新于2025-09-16 10:30:52
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Computational study on optoelectronic and charge transport properties of diketopyrrolopyrrole-based A–D–A–D–A structure molecules for organic solar cells
摘要： Eight novel diketopyrrolopyrrole (DPP)-based A–D–A–D–A structure molecules were designed for organic solar cells (OSCs) applications. In these molecules, the electron-deficient DPP and dicyanovinyl groups were used as the acceptor groups and different planar electron-rich groups were employed as the donor π-bridges. Applying the B3LYP/6–31G (d,p) and TD-B3LYP/6–31G (d,p) methods, the optoelectronic and charge transport properties were investigated. It turned out that the different π-bridges can tune effectively the frontier molecular orbital energy levels, band gap, and absorption spectra. Furthermore, the different π-bridges also affect the charge transport properties of the designed molecules. Our results suggest that the investigated molecules can serve as donor materials. Additionally, some investigated molecules can also be used as hole and/or electron transport materials for OSCs.
关键词： Optoelectronic property,Dicyanovinyl,Reorganization energy,Diketopyrrolopyrrole (DPP),Organic solar cells (OSCs)
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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Regio-regular alternating diketopyrrolopyrrole-based D <sub/>1</sub> –A–D <sub/>2</sub> –A terpolymers for the enhanced performance of polymer solar cells
摘要： We designed and synthesized regio-regular alternating diketopyrrolopyrrole (DPP)-based D1–A–D2–A terpolymers (PDPPF2T2DPP-T2, PDPPF2T2DPP-TVT, and PDPPF2T2DPP-DTT) using a primary donor (D1) [3,30-di?uoro-2,20-bithiophene (F2T2)] and a secondary donor (D2) [2,20-bithiophene (T2), (E)-1,2-di(thiophen-2-yl)ethene (TVT), or dithieno[3,2-b:20,30-d]thiophene (DTT)]. A PDPP2DT-F2T2 D–A polymer was synthesized as well to compare optical, electronic, and photovoltaic properties. The absorption peaks of the terpolymers (PDPPF2T2DPP-T2, PDPPF2T2DPP-TVT, and PDPPF2T2DPP-DTT) were longer (lmax ? 801–810 nm) than the peak of the PDPP2DT-F2T2 polymer (lmax ? 799 nm), which is associated with the high-lying HOMO levels of the terpolymers ((cid:2)5.08 to (cid:2)5.13 eV) compared with the level of the PDPP2DT-F2T2 polymer ((cid:2)5.38 eV). The photovoltaic properties of these DPP-based polymers were investigated under simulated AM 1.5G sunlight (100 mW cm(cid:2)2) with a conventional structure (ITO/PEDOT:PSS/polymer:PC71BM/Al). The open-circuit voltages (Voc) of photovoltaic devices containing the terpolymers were slightly lower (0.68–0.70 V) than the Voc of the device containing the PDPP2DT-F2T2 polymer (0.79 V). The short-circuit current (Jsc) of the PDPPF2T2DPP-DTT device was signi?cantly improved (14.14 mA cm(cid:2)2) compared with that of the PDPP2DT-F2T2 device (8.29 mA cm(cid:2)2). As a result, the power conversion e?ciency (PCE) of the PDPPF2T2DPP-DTT device (6.35%) was increased by 33% compared with that of the simple D–A-type PDPP2DT-F2T2 device (4.78%). The highest Jsc and PCE values (the PDPPF2T2DPP-DTT device) were attributed to an optimal nanoscopically mixed morphology and strong interchain packing with a high face-on orientation in the blend ?lm state. The study demonstrated that our strategy of using multiple donors in a regio-regular alternating fashion could ?ne-tune the optical, electronic, and morphological properties of D–A-type polymers, enhancing the performance of polymer solar cells.
关键词： diketopyrrolopyrrole,terpolymers,polymer solar cells,photovoltaic properties,regio-regular
更新于2025-09-12 10:27:22
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Markedly different molecular formation in DPP-based small-molecule solar cells probed by grazing-incidence wide-angle X-ray scattering
摘要： This study comprehensively explores the nanostructural properties of two diketopyrrolo[3,4-c]pyrrole-1,4-dione (DPP)-based small molecules with different alkyl side groups and their blends with the fullerene derivative PC71BM, using grazing-incidence wide-angle X-ray scattering synchrotron techniques. Preferentially relative face-on orientation within the larger and more ordered stacking phase of SM1 with its shorter side group (ethylhexyl) was observed in the majority of both pristine and blend thin films, whereas SM2 crystals showed strictly perpendicular orientation. These contrasting crystalline characteristics led to significant differences in the results, from which crystalline structure–performance property correlations are proposed. Thus, the results not only demonstrate important scientific insights into the relationship between molecular structure and crystalline formation but also provide molecular design directions that will facilitate further improvement to the morphology and performance of DPP-based small-molecule solar cells.
关键词： small-molecule donors,diketopyrrolopyrrole,grazing-incidence wide-angle X-ray scattering,molecular packing structure,small-molecule solar cells
更新于2025-09-11 14:15:04
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Rational Molecular Design towards NIR Absorption; Efficient Diketopyrrolopyrrole Derivatives for Organic Solar Cells and Photothermal Therapy
摘要： After the development of diketopyrrolopyrrole (DPP) in 1974, its derivatives have been widely explored for optoelectronic applications. In this review we discuss various donor/acceptor functionalized DPPs which are recently published and systematically compared their properties. The modification of donor functionalized DPP to tetracyanobutadiene (TCBD) bridged derivatives with improved acceptor strength, absorption towards near infra-red region have shown some exciting advancement in non-fullerene acceptors for organic solar cells and as therapeutic agents in photothermal therapy are also described. The optoelectronic properties in relation to structural changes such as change of end capping groups, donor–acceptor moieties, aromatic moiety in DPP core and number of DPP units in the molecular structure are discussed. We are expecting that the current review will provide guidelines for the exploration of new DPP based efficient materials for photovoltaic and biomedical applications.
关键词： diketopyrrolopyrrole,optoelectronic applications,photothermal therapy,organic solar cells,NIR absorption
更新于2025-09-11 14:15:04
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Regioregularity and Electron Deficiency Control of Unsymmetric Diketopyrrolopyrrole Copolymers for Organic Photovoltaics
摘要： Manipulating the electron deficiency and controlling the regioregularity of π-conjugated polymers are important for the fine-tuning of their electronic and electrochemical properties to make them suitable for an organic solar cell. Here, we report such a molecular design of unsymmetric diketopyrrolopyrrole (DPP) based copolymers with different aromatic side units of either thiophene (Th), pyridine (Py), or fluorobenzene (FBz). The unsymmetric electron acceptors of Th?DPP?Py and Th?DPP?FBz were polymerized with the electron donor of two-dimensional benzobisthiophene (BDT-Th), affording two regiorandom DPP copolymers. They exhibited contrasting molecular orbital levels and bulk heterojunction morphology in methanofullerene-blended films, leading to power conversion efficiencies of 3.75 and 0.18%, respectively. We further synthesized a regioregular DPP copolymer via sandwiching the centrosymmetric BDT-Th unit by two Th?DPP?Py units in an axisymmetric manner. The extensive characterization through morphology observation, X-ray diffraction, and space-charge-limited current mobilities highlight the case-dependent positive/negative effects of regioregularity and electron deficiency control.
关键词： diketopyrrolopyrrole,organic photovoltaics,electron deficiency,regioregularity,power conversion efficiency
更新于2025-09-11 14:15:04
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Charge Carrier Polarity Modulation in Diketopyrrolopyrrole–Based Low Band Gap Semiconductors by Terminal Functionalization
摘要： Organic semiconductors with variable charge carrier polarity are required for optoelectronic applications. Herein, we report the synthesis of three novel diketopyrrolopyrrole (DPP) based D–A molecules having three different terminal groups (amide, ester and dicyano) and studied their electronic properties. Increase in electron acceptor strength from amide to dicyano, leads to a bathochromic shift in absorption. Photoconductivity and field–effect transistor (FET) measurements confirmed that a small increase in acceptor strength can results in a large change in the charge transport properties from p–type to n–type. The molecule with amide group, DPP–Amide, exhibited a moderate p–type mobility (1.3 × 10–2 cm2V?1s?1), whereas good n–type mobilities were observed for molecules with an ester moiety, DPP–Ester (1.5 × 10–2 cm2V?1s?1) and with a dicyano group, DPP–DCV (1 × 10–2 cm2V?1s?1). The terminal functional group modification approach presented here is a simple and efficient method to alter the charge carrier polarity of organic semiconductors.
关键词： FP-TRMC,self-assembly,p-n switch,low band gap,Diketopyrrolopyrrole
更新于2025-09-04 15:30:14