Synthesis, characterization and device optimisation of new poly(benzo[1,2-b:4,5-b′]dithiophene-alt-thieno[3,4-d]thiazole) derivatives for solar cell applications

Allard, Nicolas; Zindy, Nicolas; Morin, Pierre; Wienk, MM Martijn; Janssen, Raj René; Leclerc, Mario

doi:10.1039/c5py00164a

Cited by 6 publications

(2 citation statements)

References 21 publications

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“…In 2015, Leclerc et al synthesized six BDT‐TTz polymers, which showed that the introduction of a T π ‐bridge between the donor and acceptor had no significant effect on the optical properties of the polymers. [ 110 ] However, the use of two different BDT derivatives seemed to have some effect on the polymer properties. The P4(m 6 ): PC 71 BM‐based device achieved the highest PCE of 4.4%.…”

Section: Photovoltaic Materials Based On Other Tz‐containing Heterocy...mentioning

confidence: 99%

Recent Advances in Organic Photovoltaic Materials Based on Thiazole‐Containing Heterocycles

Dong

Guo

et al. 2023

Macromol. Rapid Commun.

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Organic solar cells (OSCs) have achieved great progress, driven by the rapid development of wide bandgap electron donors and narrow bandgap non‐fullerene acceptors (NFAs). Among a large number of electron‐accepting (A) building blocks, thiazole (Tz) and its derived fused heterocycles have been widely used to construct photovoltaic materials, especially conjugated polymers. Benefiting from the electron deficiency, rigidity, high planarity, and enhanced intra/intermolecular interactions of Tz‐containing heterocycles, some related photovoltaic materials exhibit proper energy levels, optimized molecular aggregation, and active layer morphology, leading to excellent photovoltaic performance. This review focuses on the progress of Tz‐based photovoltaic materials in the field of OSCs. First, the Tz‐based donor and acceptor photovoltaic materials are reviewed. Then, the materials based on promising Tz‐containing heterocycles, mainly including thiazolo[5,4‐d]thiazole (TzTz), benzo[1,2‐d:4,5‐d’]bis(thiazole) (BBTz), and benzo[d]thiazole (BTz) are summarized and discussed. In addition, the new emerging Tz‐fused structures and their application in OSCs are introduced. Finally, perspectives and outlooks for the further development of Tz‐containing heterocycle‐based photovoltaic materials are proposed.

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Section: Photovoltaic Materials Based On Other Tz‐containing Heterocy...mentioning

confidence: 99%

Recent Advances in Organic Photovoltaic Materials Based on Thiazole‐Containing Heterocycles

Dong

Guo

et al. 2023

Macromol. Rapid Commun.

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“…In the recent literature, direct (hetero)arylation polymerization (DHAP) has been reported as a clean and cheap route to conjugated polymers compared to conventional organometallic cross-coupling reactions. − It involves a halogenated (most commonly I, Br) aromatic monomer and an aromatic substrate bearing a C–H bond activated via a Pd catalyst. The reaction typically requires the presence of a base, not only to neutralize the stoichiometric amount of the acid formed during the process but also to assist the C–H bond activation step.…”

Section: Introductionmentioning

confidence: 99%

Tin-Free Synthesis of a Ternary Random Copolymer for BHJ Solar Cells: Direct (Hetero)arylation versus Stille Polymerization

et al. 2015

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In a recent report (Eur. J. Org. Chem. 2014, 30,\ud 6583) we emphasized the importance of addressing research\ud efforts in OPV-active materials toward synthetic processes\ud scalable up to industrial production. In this context, palladiumcatalyzed\ud direct (hetero)arylation polymerization (DHAP) can\ud be a suitable approach to reduce the number of reaction steps\ud and to avoid the use of toxic reagents in the synthesis of donor\ud polymers. Random donor−acceptor copolymers have been\ud shown to be promising materials for bulk heterojunction\ud (BHJ) solar cells with high efficiencies and increased thermal\ud stability. We report here the synthesis by DHAP of a ternary\ud double-acceptor/donor random copolymer including benzo[c][1,2,5]thiadiazole and benzo[d][1,2,3]triazole as the accepting\ud units and benzo[1,2-b;4,5-b′]dithiophene as the donor moiety. The results are discussed in comparison with the synthesis of the\ud same polymer via the Stille polymerization. The coupling products formed in the early stage of the polycondensation have been\ud isolated and characterized by NMR spectroscopy to gain insight into the regiochemistry of DHAP. The polymers synthesized\ud have been tested in BHJ solar cells with PC71BM as the electron acceptor material. Power conversion efficiencies (up to 2.8%)\ud are comparable or lower (depending on the processing conditions) than those of the same polymer synthesized via the Stille\ud coupling reaction; however, the DHAP protocol is more convenient in terms of synthetic complexity

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Synthesis, Properties, and Solar Cell Performance of Poly(4‐(p‐alkoxystyryl)thiazole)s

Jäger

Schraff

Pammer

2018

Macro Chemistry & Physics

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A series of polythiazoles (PvTzs) featuring conjugated styryl sidechains equipped with different solubilizing p‐alkoxy‐groups (OR, R = n‐octyl, n‐dodecyl, 2‐ethylhexyl, 2‐hexyldecyl) is prepared by Negishi‐coupling polycondensation. Soluble material with number‐average molecular weights of up to Mn = 8.5 kDa (polydispersity (PDI) = 1.3, degree of polymerization (DPn) ≈ 20) is obtained, with a head‐to‐tail content of the PvTzs of ≈77%, as estimated from comparison with reference polymers. The polymers exhibit optical absorption properties similar to their polythiophene analogues, while their electrochemical characterization shows a significant stabilization of their frontier orbital levels. Fluorescence measurements indicate that upon excitation of the electron rich alkoxystyryl side‐chains charge transfer onto the more electron deficient polythiazole backbone occurs. This finding is corroborated by density functional theory (DFT) calculations on oligomeric model systems, which also consistently reproduce the optical properties observed for the polymers. The potentialities of these materials for applications in organic electronics can be demonstrated by their use as donor materials in organic photovoltaic cells, which exhibit higher open circuit voltages (VOC, up to 0.86 V) than P3HT‐ or analogous polythiophene‐based cells (VOC = 0.5–0.6 V).

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Synthesis, characterization and device optimisation of new poly(benzo[1,2-b:4,5-b′]dithiophene-alt-thieno[3,4-d]thiazole) derivatives for solar cell applications

Abstract: New alternating copolymers based on benzo[1,2-b:4,5-b′]-dithiophene and thieno[3,4-d]thiazole derivatives have been synthesized and their optical, electrochemical and photovoltaic properties were studied.

Cited by 6 publications

References 21 publications

Recent Advances in Organic Photovoltaic Materials Based on Thiazole‐Containing Heterocycles

Recent Advances in Organic Photovoltaic Materials Based on Thiazole‐Containing Heterocycles

Tin-Free Synthesis of a Ternary Random Copolymer for BHJ Solar Cells: Direct (Hetero)arylation versus Stille Polymerization

Synthesis, Properties, and Solar Cell Performance of Poly(4‐(p‐alkoxystyryl)thiazole)s

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