Phenylene-Bridged Perylene Monoimides as Acceptors for Organic Solar Cells: A Study on the Structure-Property Relationship.
Ontology highlight
ABSTRACT:
SUBMITTER: Schweda B
PROVIDER: S-EPMC9313791 | biostudies-literature |
REPOSITORIES: biostudies-literature
Similar Datasets
Project description:New D-π-A configured organic sensitizers featuring halogen-substituted oxindole-bridged acceptor units have been synthesized for dye-sensitized solar cells applications. Among fluorine, bromine, and iodine substitution, the cell based on bromine incorporated dye exhibited the highest efficiency. The oxindoles in these sensitizers were found to assist the electron injection through the chelation of their amide carbonyl groups to the TiO2 surface. This study provides an alternate approach for future rational dye design to gain excellent DSSC performance.
| S-EPMC7248932 | biostudies-literature
Project description:In this work, a star-shaped planar acceptor named FTr-3PDI was synthesized via ring-fusion between truxene core and three bay-linked perylene diimide (PDI) branches. Compared to the unfused non-planar acceptor Tr-3PDI, FTr-3PDI exhibits better structural rigidity and planarity, as well as more effective conjugation between truxene core and PDI branches. As a result, FTr-3PDI shows up-shifted energy levels, enhanced light absorption coefficient, increased electron mobility, and more favorable phase separation morphology in bulk-heterojunction (BHJ) blend films as compared to Tr-3PDI. Consequently, FTr-3PDI afforded higher power conversion efficiency (PCE) in BHJ solar cells when blended with a polymer donor PTB7-Th. This work demonstrates that ring-fusion is a promising molecular design strategy to combine the merits of truxene and PDI for non-fullerene acceptors used in organic solar cells.
| S-EPMC6131300 | biostudies-literature
Project description:A strategy that employs the central-core regiochemistry to develop two isomeric perylene diimide (PDI)-based small molecular acceptors (SMAs), BPT-Se and BPT-Se1, is introduced, and the effect of the central-core regiochemistry on the optical, electronic, charge-transport, photovoltaic, and morphological properties of the molecules and their devices is investigated. The PDBT-T1:BPT-Se1-based device delivers a power conversion efficiency (PCE) of 9.54% with an excellent fill factor (FF) of 73.2%, while the BPT-Se-based device yields a PCE of 7.78%. The large improvement of PCE upon isomerization of BPT-Se should be ascribed to the concurrent enhancement of FF, short circuit current ( J SC), and open circuit voltage (V OC) of the PDBT-T1:BPT-Se1 devices. The higher FF of the organic solar cells (OSCs) based on PDBT-T1:BPT-Se1 can be attributed to the higher charge dissociation and charge collection efficiency, less bimolecular combination, more balanced µ h/µ e, better molecular packing and a more favorable morphology. It is worth mentioning that the FF of 73.2% is the highest value for PDI-based SMAs OSCs to date. The result shows that regiochemistry of the central core in PDI-based SMAs greatly affects the physicochemical properties and photovoltaic performance. The success of the isomerization strategy offers exciting prospects for the molecular design of PDI-based SMAs.
| S-EPMC6425449 | biostudies-other
Project description:We designed and synthesized a series of isoindigo-based derivatives to investigate how chemical structure modification at both the 6,6'- and 5,5'-positions of the core with electron-rich and electron-poor moieties affect photophysical and redox properties as well as their solid-state organization. Our studies reveal that 6,6'-substitution on the isoindigo core results in a stronger intramolecular charge transfer band due to strong electronic coupling between the 6,6'-substituent and the core, whereas 5,5'-substitution induces a weaker CT band that is more sensitive to the electronic nature of the substituents. In the solid state, 6,6'-derivatives generally form J-aggregates, whereas 5,5'-derivatives form H-aggregates. With only two branched ethylhexyl side chains, the 6,6'-derivatives form organized lamellar structures in the solid state. The incorporation of electron-rich benzothiophene, BT, substituents further enhances ordering, likely because of strong intermolecular donor-acceptor interactions between the BT substituent and the electron-poor isoindigo core on neighboring compounds. Collectively, the enhanced photophysical properties and solid-state organization of the 6,6'-benzothiophene substituted isoindigo derivative compared to the other isoindigo derivatives examined in this study resulted in solar cells with higher power conversion efficiencies when blended with a fullerene derivative.
| S-EPMC4149328 | biostudies-literature
Project description:Triplet acceptors have been developed to construct high-performance organic solar cells (OSCs) as the long lifetime and diffusion range of triplet excitons may dissociate into free charges instead of net recombination when the energy levels of the lowest triplet state (T1 ) are close to those of charge-transfer states (3 CT). The current triplet acceptors were designed by introducing heavy atoms to enhance the intersystem crossing, limiting their applications. Herein, two twisted acceptors without heavy atoms, analogues of Y6, constructed with large ?-conjugated core and D-A structure, were confirmed to be triplet materials, leading to high-performance OSCs. The mechanism of triplet excitons were investigated to show that the twisted and D-A structures result in large spin-orbit coupling (SOC) and small energy gap between the singlet and triplet states, and thus efficient intersystem crossing. Moreover, the energy level of T1 is close to 3 CT, facilitating the split of triplet exciton to free charges.
| S-EPMC7497160 | biostudies-literature
Project description:The development of organic electron acceptor materials is one of the key factors for realizing high performance organic solar cells. Compared to traditional fullerene acceptor materials, non-fullerene electron acceptors have attracted much attention due to their better optoelectronic tunabilities and lower cost as well as higher stability. Non-fullerene organic solar cells have recently experienced a rapid increase with power conversion efficiency of single-junction devices over 14% and a bit higher than 15% for tandem solar cells. In this review, two types of promising small-molecule electron acceptors are discussed: perylene diimide based acceptors and acceptor(A)-donor(D)-acceptor(A) fused-ring electron acceptors, focusing on the effects of structural modification on absorption, energy levels, aggregation and performances. We strongly believe that further development of non-fullerene electron acceptors will hold bright future for organic solar cells.
| S-EPMC6157397 | biostudies-literature
Project description:The use of non-fullerene acceptors in organic photovoltaic (OPV) devices could lead to enhanced efficiencies due to increased open-circuit voltage (VOC) and improved absorption of solar light. Here we systematically investigate planar heterojunction devices comprising peripherally substituted subphthalocyanines as acceptors and correlate the device performance with the heterojunction energetics. As a result of a balance between VOC and the photocurrent, tuning of the interface energy gap is necessary to optimize the power conversion efficiency in these devices. In addition, we explore the role of the charge transport layers in the device architecture. It is found that non-fullerene acceptors require adjusted buffer layers with aligned electron transport levels to enable efficient charge extraction, while the insertion of an exciton-blocking layer at the anode interface further boosts photocurrent generation. These adjustments result in a planar-heterojunction OPV device with an efficiency of 6.9% and a VOC above 1 V.
| S-EPMC5538756 | biostudies-literature
Project description:The flexibility in structural design of organic semiconductors endows organic solar cells (OSCs) not only great function-tunabilities, but also high potential toward practical application. In this work, simple non-fused-ring electron acceptors are developed through two-step synthesis from single aromatic units for constructing efficient OSCs. With the assistance of non-covalent interactions, these rotatable non-fused acceptors (in solution) allow transiting into planar and stackable conformation in condensed solid, promoting acceptors not only feasible solution-processability, but also excellent film characteristics. As results, decent power conversion efficiencies of 10.27% and 13.97% can be achieved in single and tandem OSCs consisting of simple solution-cast blends, in which the fully unfused acceptors exhibit exceptionally low synthetic complexity index. In addition, the unfused acceptor and its based OSCs exhibit promising stabilities under continuous illumination. Overall, this work reveals valuable insights on the structural design of simple and effective electron acceptors with great practical perspectives.
| S-EPMC6517432 | biostudies-literature
Project description:A fused-ring electron acceptor (FREA) NDIC is designed and synthesized. Inspired by IDIC, NDIC was constructed by replacing the benzene with a naphthalene ring in its core unit. IDIC exhibits an optical bandgap of 1.60 eV and a lower lowest unoccupied molecular orbital (LUMO) energy level of -3.92 eV. In comparison, NDIC displays an optical band gap of 1.72 eV and a higher lying LUMO energy level of -3.88 eV. Due to the higher energy level, inverted devices based on NDIC exhibit a higher open circuit voltage (V oc) of 0.90 V, which is much higher than that of IDIC (0.77 V). After a series of optimizations, a power conversion efficiency (PCE) of 9.43% was obtained with a PBDB-T:NDIC blend active layer, in comparison, a PCE of 9.19% was achieved based on IDIC. Our results demonstrate that a tiny variation in the molecular structure could dramatically affect the optical and electrochemical properties, and thus the photovoltaic performance.
| S-EPMC9076117 | biostudies-literature
Project description:The active layer in a solution processed organic photovoltaic device comprises a light absorbing electron donor semiconductor, typically a polymer, and an electron accepting fullerene acceptor. Although there has been huge effort targeted to optimize the absorbing, energetic, and transport properties of the donor material, fullerenes remain as the exclusive electron acceptor in all high performance devices. Very recently, some new non-fullerene acceptors have been demonstrated to outperform fullerenes in comparative devices. This Account describes this progress, discussing molecular design considerations and the structure-property relationships that are emerging. The motivation to replace fullerene acceptors stems from their synthetic inflexibility, leading to constraints in manipulating frontier energy levels, as well as poor absorption in the solar spectrum range, and an inherent tendency to undergo postfabrication crystallization, resulting in device instability. New acceptors have to address these limitations, providing tunable absorption with high extinction coefficients, thus contributing to device photocurrent. The ability to vary and optimize the lowest unoccupied molecular orbital (LUMO) energy level for a specific donor polymer is also an important requirement, ensuring minimal energy loss on electron transfer and as high an internal voltage as possible. Initially perylene diimide acceptors were evaluated as promising acceptor materials. These electron deficient aromatic molecules can exhibit good electron transport, facilitated by close packed herringbone crystal motifs, and their energy levels can be synthetically tuned. The principal drawback of this class of materials, their tendency to crystallize on too large a length scale for an optimal heterojunction nanostructure, has been shown to be overcome through introduction of conformation twisting through steric effects. This has been primarily achieved by coupling two units together, forming dimers with a large intramolecular twist, which suppresses both nucleation and crystal growth. The generic design concept of rotationally symmetrical aromatic small molecules with extended π orbital delocalization, including polyaromatic hydrocarbons, phthalocyanines, etc., has also provided some excellent small molecule acceptors. In most cases, additional electron withdrawing functionality, such as imide or ester groups, can be incorporated to stabilize the LUMO and improve properties. New calamitic acceptors have been developed, where molecular orbital hybridization of electron rich and poor segments can be judiciously employed to precisely control energy levels. Conformation and intermolecular associations can be controlled by peripheral functionalization leading to optimization of crystallization length scales. In particular, the use of rhodanine end groups, coupled electronically through short bridged aromatic chains, has been a successful strategy, with promising device efficiencies attributed to high lying LUMO energy levels and subsequently large open circuit voltages.
| S-EPMC4652276 | biostudies-other