Improving optoelectronic and charge transport properties of D–π–D type diketopyrrolopyrrole-pyrene derivatives as multifunctional materials for organic solar cell applications

Jin, Ruifa; Li, Kexin; Han, Xueli

doi:10.1039/c9ra04304g

Cited by 10 publications

(4 citation statements)

References 64 publications

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“…It has a very low HOMO–LUMO gap − and exhibits a very strong S 0 -to-S 1 transition (i.e., band I absorption) because its low band gap comes from its particularly high HOMO level and moderately-low LUMO level . Owing to its strong light absorption, planarity, − high carrier mobility, photochemical stability, and facile synthesis, T-DPP-T has been a popular pulling unit combined with various pushing units for photovoltaic/electronic applications. − The optimized geometry of T-DPP-T (whose long alkyl side chains on DPP are replaced by methyl groups for simplicity) and its torsion energy curve, both calculated as a function of the S-C-C-N dihedral angle at the B3LYP/6-311G** level of density functional theory (DFT) implemented in Jaguar, indeed support its planarity (Figure a).…”

Section: Resultsmentioning

confidence: 99%

Narrow-Wide Copolymer for Strong Red-Color-Selective Absorption

et al. 2022

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Full-color image sensors for retinal prosthesis and artificial vision would require organic RGB-color-selective photodiode components. The most challenging components are those for red-selective absorption. Molecular dyes such as phthalocyanine and squaraine require vacuum deposition, and red-light absorption achieved by solution-processed push−pull copolymers is often accompanied by higher-energy absorption in green and blue regions. Push−pull copolymers designed to suppress such highenergy absorption show their low-energy absorption in the IR region rather than in the red region. Herein, we define red selectivity (RS) of a polymer as the ratio of its red-region absorption (the area under the absorption spectrum between 625 and 800 nm) to its total absorption in the visible and near-IR regions (the area between 400 and 1000 nm) and propose a narrow-wide (rather than push−pull) design rule for RS-enhancing copolymers, (1) highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) localized in the narrow-band-gap unit and HOMO−1 and LUMO+1 localized in the other wide-band-gap unit and (2) hybridization between the two units minimized by introducing a twist in the backbone. Doping them with red-selective nonfullerene acceptors would enhance charge transport and sensitivity without sacrificing RS. Such polymers tuned for strong absorption of skin-penetrating red light would be also useful for spatially controlled wireless (noninvasive) power supply to photovoltaic-coupled organic (conformable/ biocompatible) electronic implant.

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Section: Resultsmentioning

confidence: 99%

Narrow-Wide Copolymer for Strong Red-Color-Selective Absorption

et al. 2022

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“…For this purpose, first of all, BDIDR1 was optimized at various levels, such as B3LYP, CAM-B3LYP, MPW1PW91, M06, and M06-2X, with a 6-31G(d,p) basis set − in chloroform. According to a literature survey, the 6-31G(d,p) basis set is used for investigating the photovoltaic and optoelectronic parameters of organic solar cells . After the successful optimization of BDIDR1 , the absorption characteristics of BDIDR1 were computed at the aforementioned functional of the TD-DFT approach in chloroform and compared with the reported experimental value (734 nm) to select a suitable functional.…”

Section: Methodsmentioning

confidence: 99%

“…According to a literature survey, the 6-31G(d,p) basis set is used for investigating the photovoltaic and optoelectronic parameters of organic solar cells. 23 After the successful optimization of BDIDR1, the absorption characteristics of BDIDR1 were computed at the aforementioned functional of the TD-DFT approach in chloroform and compared with the reported experimental value 24 (734 nm) to select a suitable functional. The following results were obtained for λ max : B3LYP = 583.592 nm, CAM-B3LYP = 462.610 nm, MPW1PW91 = 634.255 nm, M06 = 778.893 nm, and M06-2X = 468.767 nm, in conjunction with the 6-31G(d,p) basis set.…”

Section: In Chloroformmentioning

confidence: 99%

Theoretical Expedition for Enhancing Photovoltaic Performance: DFT Investigation of Benzo[c][1,2,5] thiadiazole-Based Scaffolds for Organic Solar Cells

Khalid,

Sagir,

Zahid

et al. 2024

Ind. Eng. Chem. Res.

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Currently, the development of efficient photovoltaic materials is accelerated by the use of fullerene-free small molecular acceptors. Therefore, we designed and studied the optoelectronic characteristics of eight new A 1 -D-A 2 -D-A 1 configured benzothiazole-based molecules (BDIDZ2−BDIDZ9), obtained by the structural modification of the reference molecule (BDIDR1) with various acceptors. The M06/6-31G(d,p) functional was selected through a benchmarked study using DFT and the experimental UV−vis values of BDIDR1. Various parameters, like transition density matrix (TDM), frontier molecular orbitals (FMOs), binding energy (Eb), open-circuit voltage (V oc ), reorganization energies (RE) for holes and electrons, and density of states (DOS), were used to understand the optoelectronic properties of the designed compounds. Structural tailoring via the modification of terminal acceptors minimized the energy gap and shifted the absorption spectra toward redshift (752.37−778.89 nm), resulting in an enhanced charge transfer toward the LUMO from the HOMO. Moreover, the open-circuit voltage was calculated by HOMO PBDB-T −LUMO acceptor and compared with the parent chromophore. All of the derivatives showed a relatively higher opencircuit value. The lower reorganization energies in the holes and electrons suggested a higher rate of charge mobility. Interestingly, all of the modified chromophores displayed a better optoelectronic response than the reference molecule. The above-mentioned results indicate that molecular engineering with benzothiophene acceptors improves the photovoltaic response of nonfullerene chromophores and encourages experimentalists to develop high-efficacy photovoltaic devices.

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“…The value of # K as well as the LUMO and HOMO energy levels of D-A structures can be tuned due to intramolecular charge transfer (ICT) between the D and A groups; furthermore, low # K favors more effective optical absorption, providing a higher T ål . Therefore, this situation decreases # K in the DPP-substituted systems enhances ICT between the substituents and the DPP core, which extends the absorption spectrum to longer wavelengths 9,26,77,78 -see also discussion of CT effects below. The increasing order of ! "…”

Section: Optoelectronic and Photovoltaic Propertiesmentioning

confidence: 96%

Photophysical properties of donor(D)-acceptor(A)-donor(D) diketopyrrolopyrrole (A) systems as donors for applications to organic electronic devices

Rosa,

Borges Jr

2024

Preprint

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Fourteen substituted diketopyrrolopyrrole (DPP) molecules in a donor (D)-acceptor (DPP)-donor (D) arrangement were designed. We employed density functional theory (DFT), time-dependent DFT and the ab initio wave function second-order algebraic diagrammatic construction (ADC(2)) methods to investigate theoretically these systems. The aromatic substituents have one, two or three hetero- and non-hetero rings. We comprehensively investigated their optical, electronic and charge transport properties to evaluate potential applications in organic electronic devices. We found that the substituents based on one, two or three aromatic rings bonded to the DPP core functioning as a donor can improve the efficiency of an organic solar cell by fine-tuning the HOMO/LUMO levels to match acceptors in a bulk heterojunctions with PC61BM and the non-fullerene small-molecule ITIC (3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone)-5,5,11,11-tetrakis(4 hexylphenyl)-dithieno[2,3-d:2′,3′-d′]-s-indaceno[1,2-b:5,6-b′]-dithiophene) acceptors. Several properties of interest for organic photovoltaic devices were computed. We show that the investigated molecules are promising for applications as donor materials when combined with typical acceptors in bulk heterojunctions because they have appreciable energy conversion efficiencies resulting from their low ionization potentials and high electronic affinities. This scenario allows a more effective charge separation and reduces the recombination rates. A comprehensive charge transfer analysis shows that the D – A (DDP) – D systems have significant intramolecular charge transfer, further confirming their promise as candidates for donor materials in solar cells. The significant photophysical properties of DPP derivatives, including the computed high quantum yields of fluorescence emission, also allow these materials to be used in organic light-emitting diodes (OLEDs).

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Improving optoelectronic and charge transport properties of D–π–D type diketopyrrolopyrrole-pyrene derivatives as multifunctional materials for organic solar cell applications

Abstract: A series of novel diketopyrrolopyrrole-pyrene-based molecules have been designed as donor materials with suitable FMOs to match those of typical acceptors PC61BM and PC71BM and ambipolar charge transport materials in SMOSCs applications.

Cited by 10 publications

References 64 publications

Narrow-Wide Copolymer for Strong Red-Color-Selective Absorption

Narrow-Wide Copolymer for Strong Red-Color-Selective Absorption

Theoretical Expedition for Enhancing Photovoltaic Performance: DFT Investigation of Benzo[c][1,2,5] thiadiazole-Based Scaffolds for Organic Solar Cells

Photophysical properties of donor(D)-acceptor(A)-donor(D) diketopyrrolopyrrole (A) systems as donors for applications to organic electronic devices

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