Benzothiadiazole-based push-pull copolymers – Balancing synthetic complexity against organic solar cell efficiency

Valkeneers, Kaat; Vandewal, Koen; Maes, Wouter

doi:10.1016/j.orgel.2022.106667

Cited by 5 publications

(2 citation statements)

References 277 publications

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“…In this contribution, we designed and characterized five A-π-D-π-A SMs based on the A-D-A reference structure. The reference DRCN5T chosen in this work is characterized by high photovoltaic performance and is composed of an oligothiophene core donor block and two 2-(3-ethyl-4-oxothiazolidin-2-ylidene)malononitrile end-capped acceptor blocks. , The designed materials are push–pull systems, where the alternating arrangement of electron-deficient and electron-rich blocks along the conjugated framework efficiently extends the electron delocalization, enhances the light-harvesting abilities, and improves the charge dissociation for efficient OPVs applications. , The selected π-spacer for the new materials design is 2,1,3-benzothiadiazole (BT), which is one of the most popular fused heterocyclic building blocks for organic electronics thanks to its outstanding optoelectronic properties . As depicted in Figure , the designed materials, labeled D1–D5, contain different BT derivatives in which carbon atoms are replaced by electron-donating groups such as nitrogen atoms, or electron-withdrawing groups such as fluorine or cyano groups .…”

Section: Introductionmentioning

confidence: 99%

Effect of Benzothiadiazole-Based π-Spacers on Fine-Tuning of Optoelectronic Properties of Oligothiophene-Core Donor Materials for Efficient Organic Solar Cells: A DFT Study

Zaier,

Martel,

Antosiewicz

2023

J. Phys. Chem. A

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In this work, five novel A-π-D-π-A type molecules D1–D5 were designed by adding unusual benzothiadiazole derivatives as π-spacer blocks to the efficient reference molecule DRCN5T for application as donor materials in organic solar cells (OSCs). Based on a density functional theory approach, a comprehensive theoretical study was performed with different functionals (B3LYP, B3LYP-GD3, B3LYP-GD3BJ, CAM-B3LYP, M06, M062X, and wB97XD) and with different solvent types (PCM and SMD) at the extended basis set 6-311+g(d,p) to evaluate the structural, optoelectronic, and intramolecular charge transfer properties of these molecules. The B3LYP-GD3BJ hybrid functional was used to optimize the studied molecules in CHCl 3 solution with the SMD model solvent as it provided the best results compared to experimental data. Transition density matrix maps were simulated to examine the hole–electron localization and the electronic excitation processes in the excited state, and photovoltaic parameters including open-circuit photovoltage and fill factor were investigated to predict the efficiency of these materials. All the designed materials showed promising optoelectronic and photovoltaic characteristics, and for most of them, a red shift. Out of the proposed molecules, [1,2,5]thiadiazolo[3,4- d ]pyridazine was selected as a promising π-spacer block to evaluate its interaction with PC 61 BM in a composite to understand the charge transfer between the donor and acceptor subparts. Overall, this study showed that adding π-spacer building blocks to the molecular structure is undoubtedly a potential strategy to further enhance the performance of donor materials for OSC applications.

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Section: Introductionmentioning

confidence: 99%

Effect of Benzothiadiazole-Based π-Spacers on Fine-Tuning of Optoelectronic Properties of Oligothiophene-Core Donor Materials for Efficient Organic Solar Cells: A DFT Study

Zaier,

Martel,

Antosiewicz

2023

J. Phys. Chem. A

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“…Thienothiadiazole-and benzothiadiazole-based units with the thiadiazole nucleus are among the most interesting A blocks [31][32][33][34][35][36][37][38][39]. The benzothidiazole and its derivatives are of interest, namely for the syntheses of D-A copolymers for photovoltaic applications [40][41][42][43][44]. On the other hand, carbazole derivatives belong to the interesting D blocks.…”

Section: Introductionmentioning

confidence: 99%

Donor-Acceptor Copolymers with 9-(2-Ethylhexyl)carbazole or Dibenzothiophene-5,5-dioxide Donor Units and 5,6-Difluorobenzo[c][1,2,5]thiadiazole Acceptor Units for Photonics

Cimrová,

Babičová,

Guesmi

et al. 2023

Nanomaterials

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Semiconducting polymers, particularly of the third generation, including donor-acceptor (D-A) copolymers, are extensively studied due to their huge potential for photonic and electronic applications. Here, we report on two new D-A copolymers, CP1 and CP2, composed of different electron-donor (D) units: 9-(2-ethylhexyl)carbazole or dibenzothiophene-5,5-dioxide, respectively, and of 4,7-bis(4′-(2-octyldodecyl)thiophen-2′-yl)-5,6-difluorobenzo[c][1,2,5]thiadiazole building block with central 5,6-difluorobenzo[c][1,2,5]thiadiazole electron-acceptor (A) units, which were synthesized by Suzuki coupling in the high-boiling solvent xylene and characterized. The copolymers exhibited very good thermal and oxidation stability. A copolymer CP1 with different molecular weights was prepared in order to facilitate a comparison of CP1 with CP2 of comparable molecular weight and to reveal the relationship between molecular weight and properties. The photophysical, electrochemical, and electroluminescence properties were examined. Intense red photoluminescence (PL) with higher PL efficiencies for CP1 than for CP2 was observed in both solutions and films. Red shifts in the PL thin film spectra compared with the PL solution spectra indicated aggregate formation in the solid state. X-ray diffraction measurements revealed differences in the arrangement of molecules in thin films depending on the molecular weight of the copolymers. Light-emitting devices with efficient red emission and low onset voltages were prepared and characterized.

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Liquid benzothiadiazole-based organic luminophores emitting light from the blue to red spectral region: synthesis, properties, and application in liquid scintillators

Dyadishchev,

Balakirev,

Kalinichenko

et al. 2024

Dyes and Pigments

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Benzothiadiazole-based push-pull copolymers – Balancing synthetic complexity against organic solar cell efficiency

Cited by 5 publications

References 277 publications

Effect of Benzothiadiazole-Based π-Spacers on Fine-Tuning of Optoelectronic Properties of Oligothiophene-Core Donor Materials for Efficient Organic Solar Cells: A DFT Study

Effect of Benzothiadiazole-Based π-Spacers on Fine-Tuning of Optoelectronic Properties of Oligothiophene-Core Donor Materials for Efficient Organic Solar Cells: A DFT Study

Donor-Acceptor Copolymers with 9-(2-Ethylhexyl)carbazole or Dibenzothiophene-5,5-dioxide Donor Units and 5,6-Difluorobenzo[c][1,2,5]thiadiazole Acceptor Units for Photonics

Liquid benzothiadiazole-based organic luminophores emitting light from the blue to red spectral region: synthesis, properties, and application in liquid scintillators

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