Design of Acceptors with Suitable Frontier Molecular Orbitals to Match Donors via Substitutions on Perylene Diimide for Organic Solar Cells

Lv, Xiaoli; Li, Zhuoxin; Li, Songyang; Luan, Guoyou; Liang, Dapeng; Tang, Shanshan; Jin, Ruifa

doi:10.3390/ijms17050721

Cited by 12 publications

(6 citation statements)

References 43 publications

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“…By contrast, for the smallest active compounds (23), the HOMO and LUMO are almost dispersed across the entire molecular region. These results suggest the most active compounds have acceptor-donator behavior, as reported before in several studies [55][56][57][58][59][60][61][62][63].…”

Section: Molecular Orbitalssupporting

confidence: 87%

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

2020

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Twenty-four cannabinoids active against MRSA SA1199B and XU212 were optimized at WB97XD/6-31G(d,p), and several molecular descriptors were obtained. Using a multiple linear regression method, several mathematical models with statistical significance were obtained. The robustness of the models was validated, employing the leave-one-out cross-validation and Y-scrambling methods. The entire data set was docked against penicillin-binding protein, iso-tyrosyl tRNA synthetase, and DNA gyrase. The most active cannabinoids had high affinity to penicillin-binding protein (PBP), whereas the least active compounds had low affinities for all of the targets. Among the cannabinoid compounds, Cannabinoid 2 was highlighted due to its suitable combination of both antimicrobial activity and higher scoring values against the selected target; therefore, its docking performance was compared to that of oxacillin, a commercial PBP inhibitor. The 2D figures reveal that both compounds hit the protein in the active site with a similar type of molecular interaction, where the hydroxyl groups in the aromatic ring of cannabinoids play a pivotal role in the biological activity. These results provide some evidence that the anti-Staphylococcus aureus activity of these cannabinoids may be related to the inhibition of the PBP protein; besides, the robustness of the models along with the docking and Quantitative Structure–Activity Relationship (QSAR) results allow the proposal of three new compounds; the predicted activity combined with the scoring values against PBP should encourage future synthesis and experimental testing.

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Section: Molecular Orbitalssupporting

confidence: 87%

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

2020

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“…Previous studies demonstrated that frontier molecular orbitals (FMOs) are of critical importance in evaluating candidate compounds for enabling ultrafast interfacial electron transfer. 18,19 In accordance with these findings, computational investigations for the target dye molecules revealed that both HOMO and LUMO orbitals are explicitly localized on the SubPc backbone. The band gap of the compound series increases in the order of SubPc 1 (2.34 eV) < SubPc 2 (2.55 eV) < SubPc 3 (2.71 eV).…”

Section: Table 1 Electrochemical and Optical Properties Of The Subpht...supporting

confidence: 67%

Subphthalocyanines for Visible-Light-Driven Hydrogen Evolution: Tuning Photocatalytic Performance with Molecular Design

Güntay,

Dogan,

Killi

et al. 2023

ACS Appl. Energy Mater.

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In this work, a series of subphthalocyanines (SubPcs) with a carboxylic acid anchoring group at the axial position were used as photosensitizers of TiO2 for photocatalytic hydrogen evolution from water under visible light irradiation. SubPc derivatives with various peripheral substituents were successfully prepared to systematically investigate the dependence of photocatalytic performance on electron-donating units (i.e., bisthiophene or thioether) at the peripheral position of the SubPcs. SubPc 2/TiO2/Pt shows the best photocatalytic activity among the three dye-sensitized photocatalysts, with a hydrogen evolution rate of 1.104 mmol·g–1·h–1. After 24 h irradiation, SubPc 2/TiO2/Pt achieved a remarkable catalytic activity for the production of H2 (19.96 mmol·g–1) with a TON value of 40 734 and a high STH efficiency of 2.1%. Density functional theory (DFT) and time-dependent DFT (TD-DFT) approaches were used to elucidate further structural and electrical properties, including the interaction patterns of tailored SubPcs. It is worth noting that the theoretical computations exhibit good conformity with the empirical data. The predicted fluctuations in photocatalytic activity detected in SubPc systems were shown to be closely associated with frontier molecular orbital (FMO) characteristics, noncovalent interaction (NCI) patterns, and the electron-donating nature of the fragments located at the peripheral positions.

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“…Recent advances in p-type organic semiconductors have fulfilled many of the requirements for use in diverse applications; − however, n-type materials, needed for diodes, complementary circuits, and solar cells, continue to present challenges. − One of the major hurdles remaining is the vulnerability of n-type charge carriers to ambient conditions. So far, the mechanisms by which the electron mobility of organic thin-film transistors (OTFTs) degrades during long-term storage in air (or in other environments that contain oxygen) are still not clear. , de Leeuw et al first discussed this issue and ascribed the drop in mobility to electron trapping by the most common reactive species in an ambient atmosphere, H 2 O, and O 2 .…”

Section: Introductionmentioning

confidence: 99%

Ambient Degradation of Perylene Diimide-Based Organic Transistors: Hidden Role of Ozone and External Electric Field

et al. 2018

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A thorough interpretation on the mechanisms that control the degradation of the electrical performance of organic thin-film transistors (OTFTs) during exposure to ambient environments is still developing. This is particularly true for n-type OTFTs. By performing density functional theory calculations, we have proposed a different degradation pathway of perylene diimide in ambient air. Compared to the most common ambient oxidant, O 3 , though seldom considered, can easily react with >CC< in the π-conjugated charge-transfer center forming stable ozonides, which could be the underlying cause for relevant device failures. It is noteworthy that external electric fields which are ubiquitous while often overlooked in electronic devices can either accelerate or hamper the degradation process depending on the field direction. This finding underlines that in a rigid device configuration where electrodes are largely fixed, the way the molecules align on the substrate is pivotal to their ambient stability. Among the tested substituents, cyanation at the periphery of the perylene core resists O 3 /O 2 attack and favors electron transport by lowering the internal reorganization energy. This work constitutes the first step on understanding the interplay of interfacial oxidations and molecular charge-transport properties toward modeling the bulk electrical performance.

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Design of Acceptors with Suitable Frontier Molecular Orbitals to Match Donors via Substitutions on Perylene Diimide for Organic Solar Cells

Cited by 12 publications

References 43 publications

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

Subphthalocyanines for Visible-Light-Driven Hydrogen Evolution: Tuning Photocatalytic Performance with Molecular Design

Ambient Degradation of Perylene Diimide-Based Organic Transistors: Hidden Role of Ozone and External Electric Field

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