Dataset Information

Pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP) End Capped with Napthalimide or Phthalimide: Novel Small Molecular Acceptors for Organic Solar Cells.

ABSTRACT: We introduce two novel solution-processable electron acceptors based on an isomeric core of the much explored diketopyrrolopyrrole (DPP) moiety, namely pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP). The newly designed and synthesized compounds, 6,6'-[(1,4-bis{4-decylphenyl}-2,5-dioxo-1,2,4,5-tetrahydropyrrolo[3,2-b]pyrrole-3,6-diyl)bis(thiophene-5,2-diyl)]bis[2-(2-butyloctyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione] (NAI-IsoDPP-NAI) and 5,5'-[(1,4-bis{4-decylphenyl}-2,5-dioxo-1,2,4,5-tetrahydropyrrolo[3,2-b]pyrrole-3,6-diyl)bis(thiophene-5,2-diyl)]bis[2-(2-butyloctyl)isoindoline-1,3-dione] (PI-IsoDPP-PI) have been synthesized via Suzuki couplings using IsoDPP as a central building block and napthalimide or phthalimide as end-capping groups. The materials both exhibit good solubility in a wide range of organic solvents including chloroform (CF), dichloromethane (DCM), and tetrahydrofuran (THF), and have a high thermal stability. The new materials absorb in the wavelength range of 300-600 nm and both compounds have similar electron affinities, with the electron affinities that are compatible with their use as acceptors in donor-acceptor bulk heterojunction (BHJ) organic solar cells. BHJ devices comprising the NAI-IsoDPP-NAI acceptor with poly(3-n-hexylthiophene) (P3HT) as the donor were found to have a better performance than the PI-IsoDPP-PI containing cells, with the best device having a VOC of 0.92 V, a JSC of 1.7 mAcm-2, a FF of 63%, and a PCE of 0.97%.

SUBMITTER: Do TT

PROVIDER: S-EPMC7587392 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP) End Capped with Napthalimide or Phthalimide: Novel Small Molecular Acceptors for Organic Solar Cells.

Do Thu Trang TT Stephen Meera M Chan Khai Leok KL Manzhos Sergei S Burn Paul L PL Sonar Prashant P

Molecules (Basel, Switzerland) 20201014 20

We introduce two novel solution-processable electron acceptors based on an isomeric core of the much explored diketopyrrolopyrrole (DPP) moiety, namely pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP). The newly designed and synthesized compounds, 6,6'-[(1,4-bis{4-decylphenyl}-2,5-dioxo-1,2,4,5-tetrahydropyrrolo[3,2-b]pyrrole-3,6-diyl)bis(thiophene-5,2-diyl)]bis[2-(2-butyloctyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione] (NAI-IsoDPP-NAI) and 5,5'-[(1,4-bis{4-decylphenyl}- ...[more]

PMID: 33066513

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Project description:Small-molecule (SM)-based organic solar cells (OSCs) have dominated the photovoltaic industry on account of their efficient optical and electronic properties. This quantum mechanical study addresses a DFT study of pentacyclic aromatic bislactam (PCL)-based small molecules for extremely proficient OSCs. Five novel small molecules (PCLM1-PCLM5) retaining the A-π-A-π-D-π-A-π-A arrangement were fabricated from the reference PCLR. At the MPW1PW91/6-31G** level of theory, detailed profiling of these novel molecules was performed by accurately following DFT, along with the time-dependent density functional theory (TD-DFT) hypothetical simulations to analyze the UV-visible absorption (λmax), light-harvesting efficiency (LHE), dipole moment (μ), fill factor (FF), open-circuit voltage (V OC), power conversion efficiency (PCE), frontier molecular orbitals (FMOs), binding energy (E b), density of states (DOS), electrostatic potential (ESP), and transition density matrix (TDM) plots. Alteration of peripheral acceptors in all of the molecular structures drastically modified their charge-transfer properties, such as a strong light-harvesting capability in the range of 0.9993-0.9998, reduced exciton E b (from 0.34 to 0.39 eV), a reduced bandgap (E g) in the range of 1.66-1.99 eV, an elevated λmax (775-959 nm) along with a higher μ in the solvent phase (1.934-7.865 D) when studied in comparison with PCLR, possessing an LHE of 0.9986, an E b of 0.40, an E g 2.27 eV, λmax at 662 nm, and a μ of 0.628 D. The FMO analysis revealed the uniform dispersal of charge density entirely along the highest occupied (HOMO) and lowest unoccupied (LUMO) molecular orbitals in newly constructed moieties. Electron as well as hole mobility rates, V OC, FF, and PCE of all novel molecules (PCLM1-PCLM5) were higher as compared with those of PCLR, ultimately making them exceptional candidates for solar devices. Focusing on the outcomes, terminal acceptor modification was found to be a suitable method for the development of highly tuned OSCs in the future.

Dataset Information

Pyrrolo[3,2-b]pyrrole-1,4-dione (IsoDPP) End Capped with Napthalimide or Phthalimide: Novel Small Molecular Acceptors for Organic Solar Cells.

Publications

Pyrrolo[3,2-<i>b</i>]pyrrole-1,4-dione (IsoDPP) End Capped with Napthalimide or Phthalimide: Novel Small Molecular Acceptors for Organic Solar Cells.

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