Covalently linked donor–acceptor dyad for efficient single material organic solar cells

Lucas, Sebastian; Leydecker, Tim; Samorı́, Paolo; Mena‐Osteritz, Elena; Bäuerle, Peter

doi:10.1039/c9cc07179b

Cited by 34 publications

(33 citation statements)

References 25 publications

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“…The general synthetic route to the targeted D–A dyads with varying alkyl ester chain lengths, which was already established for dyad 2 , [ 14 ] is shown in Scheme and detailed synthetic procedures are given in Supporting Information (SI). Among the various possibilities to functionalize fullerenes, we considered the esterification of readily available fullerene carboxylic acid (PC 61 BA) 15 with alcohols.…”

Section: Resultsmentioning

confidence: 99%

“…TGA traces of dyad 1 (black curve), 2 (blue curve), [ 14 ] and 3 (red curve) with a heating rate of 10 °C min −1 (right).…”

Section: Resultsmentioning

confidence: 99%

“…J– V characteristics of optimized solar cells with dyads 1 – 3 as the photoactive layer using the cell architecture: glass/ITO/PEDOT:PSS/dyad 1 – 3 /LiF/Al under 100 mW cm −2 AM 1.5G illumination (full lines) and in the dark (dotted lines) in the pristine state (left); after SVA (CS 2 , 30 s) (right). Dyad 1 (black), dyad 2 (blue), [ 14 ] and dyad 3 (red).…”

Section: Resultsmentioning

confidence: 99%

“…It should be noted here that for dyad 2 SVA with chloroform for 25 s gave, with 3.39% PCE, a slightly better result (Table S4, Supporting Information). [ 14 ]…”

Section: Resultsmentioning

confidence: 99%

“…We recently developed a D-A dyad comprising a dithienopyrrol (DTP)-cored oligomeric donor, which was covalently linked to PC 61 BM through a ten-atom alkyl ester spacer, and reported a PCE of 3.4% in SMOSCs. [14] In this novel molecular design, components of the well-performing biphasic BHJ-OSC system, oligomer 16 as donor blended with PC 61 BM as acceptor, were covalently linked to form molecular materials for use as the sole photoactive component in SMOSCs (Figure 1). [15][16][17] In this work, we now describe the structural variation and full characterization of this novel D-A dyad design by varying the chain length of the flexible spacer, resulting in a series of dyads 1-3 with 8, 10, and 12 atoms separating the donor and acceptor ( Figure 1).…”

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Molecular Donor–Acceptor Dyads for Efficient Single‐Material Organic Solar Cells

et al. 2020

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Dedicated to Professor Franz Effenberger on the occasion of his 90th birthday 1. Introduction Covalently linked donor-acceptor (D-A) dyads, triads, and multiads have been extensively investigated in the context of photoinduced energy and charge transfer (CT) processes, which are fundamental for natural photosynthesis, but as well important for the function of organic solar cells. [1,2] The nature and length of the molecular spacer bridging D and A, flexible nonconjugated or rod-like conjugated, polar or nonpolar, play an important role for the various fundamental processes such as excitation and energy transfer, CT, charge separation, and recombination. [3] CT is also dependent on the environment, [4] which severely comes into play for the photoinduced elementary processes of molecular D-A systems in the solid state, a scenario, encountered in organic electronic devices. In this respect, in thin films, aggregation of the molecules into supramolecular assemblies to form photoactive nanostructures with well-segregated A and D domains and their orientation relative to the substrate play a major role for efficient organic solar cells. [5] As a consequence, the tailoring of molecular properties in D-A systems is an important aspect in the overall structural design for tuning and controlling distance-dependent CT, whereby intermolecular interactions and self-assembly determine charge separation in thin films. The understanding and Single-material organic solar cells (SMOSCs) promise several advantages with respect to prospective applications in printed large-area solar foils. Only one photoactive material has to be processed and the impressive thermal and photochemical long-term stability of the devices is achieved. Herein, a novel structural design of oligomeric donor-acceptor (D-A) dyads 1-3 is established, in which an oligothiophene donor and fullerene acceptor are covalently linked by a flexible spacer of variable length. Favorable optoelectronic, charge transport, and self-organization properties of the D-A dyads are the basis for reaching power conversion efficiencies up to 4.26% in SMOSCs. The dependence of photovoltaic and charge transport parameters in these ambipolar semiconductors on the specific molecular structure is investigated before and after post-treatment by solvent vapor annealing. The inner nanomorphology of the photoactive films of the dyads is analyzed with transmission electron microscopy (TEM) and grazingincidence wide-angle X-ray scattering (GIWAXS). Combined theoretical calculations result in a lamellar supramolecular order of the dyads with a D-A phase separation smaller than 2 nm. The molecular design and the precise distance between donor and acceptor moieties ensure the fundamental physical processes operative in organic solar cells and provide stabilization of D-A interfaces.

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Section: Resultsmentioning

confidence: 99%

“…TGA traces of dyad 1 (black curve), 2 (blue curve), [ 14 ] and 3 (red curve) with a heating rate of 10 °C min −1 (right).…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…It should be noted here that for dyad 2 SVA with chloroform for 25 s gave, with 3.39% PCE, a slightly better result (Table S4, Supporting Information). [ 14 ]…”

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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Molecular Donor–Acceptor Dyads for Efficient Single‐Material Organic Solar Cells

et al. 2020

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Molecular Oligothiophene–Fullerene Dyad Reaching Over 5% Efficiency in Single‐Material Organic Solar Cells

Aubele

Kraus

et al. 2021

Advanced Materials

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solar cells. [2][3][4][5][6][7][8][9] Typically, polymeric or oligomeric materials comprising covalently linked electron-rich donor (D) and electron-deficient acceptor (A) units are developed. In most examples D and A are connected by flexible insulating linkers of various lengths corresponding to a molecular bulk heterojunction model, whereas only few have rigid π-conjugated linkers or are directly connected. [1] Among the ambipolar D-A polymers, structurally challenging "double cable" polymers with high synthetic complexity [2][3][4][5] very recently showed significantly improved power conversion efficiencies (PCE) to over 8.4% in SMOSCs. In these materials, a lamellar phase-separation of D and A units is typically achieved at higher temperatures (up to 230 °C) resulting in solar cells with high thermal and light stability. [1c,3-5] Currently, these results have been outperformed by random D-A block copolymers [6][7][8] reaching a PCE of 8.6% [7] and even very promising 11.3% [8] catching the 10% technological barrier for industrial applications. [1c,10] It is well accepted that structurally defined semiconducting molecular materials have particular advantages such as monodispersity and reproducibility over polydisperse polymers, which contain chain length distributions and defects to a certain extent. [11] Various oligomeric D-A dyads and triads have been prepared and optimized for SMOSCs over time, [1] and general structural concepts include: 1) D and A are directly connected in an "in-chain" approach leading to fully π-conjugated alternating D-A systems. The best result in this category was achieved with oligo(fluorene-alt-bithiophene)perylene diimide dyads, which after post-treatment with solvent vapor annealing (SVA) gave device performances of up to 1.75% PCE; [12] 2) D and A are linearly linked via flexible linkers in the so-called "side-chain" approach in an 1:1 or 1:2 ratio, whereby an oligothiophene-PC 71 BM fullerene dyad recently described by Min et al. reached a PCE of 3.22% in SMOSCs; [13] 3) Similar to the subunits in "double cable" polymers, oligomeric donor backbones were substituted at the central unit with pending PC 61 BM or PC 71 BM fullerenes in a "T-shaped" fashion, but typically reached efficiencies of only below 2%. [1] An improved performance of up to 2.5% PCE was obtained by the attachment of non-fullerenic perylene diimide side chains to a conjugated cooligomer backbone comprising diketopyrrolopyrrole and benzodithiophene units. [14] We recently could further improve the performance of SMOSCs in this category by developing ambipolar "T-shaped" D-A dyads 1-3 consisting of a dithienopyrrole A novel donor-acceptor dyad, 4, in which the conjugated oligothiophene donor is covalently connected to fullerene PC 71 BM by a flexible alkyl ester linker, is synthesized and applied as photoactive layer in solution-processed single-material organic solar cells (SMOSCs). Excellent photovoltaic performance, including a high short-circuit current density (J SC ) of 13.56 mA cm −2 , is achieved,...

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Three‐in‐One Strategy Enables Single‐Component Organic Solar Cells with Record Efficiency and High Stability

Cheng,

Huang,

Mao

et al. 2024

Advanced Materials

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Single‐component organic solar cells (SCOSCs) with covalently bonding donor and acceptor are becoming increasingly attractive because of their superior stability over traditional multi‐component blend OSCs. Nevertheless, the efficiency of SCOSCs is far behind the state‐of‐the‐art multi‐component OSCs. Herein, by combination of the advantages of three‐component and single‐component devices, we report an innovative three‐in‐one strategy to boost the performance of SCOSCs. In this three‐in‐one strategy, three independent components (PM6, D18, and PYIT) are covalently linked together to create a new single‐component active layer based on ternary conjugated block copolymer (TCBC) PM6‐D18‐b‐PYIT by a facile polymerization. Precisely manipulating the component ratios in the polymer chains of PM6‐D18‐b‐PYIT is able to broaden light utilization, promote charge dynamics, optimize and stabilize film morphology, contributing to the simultaneously enhanced efficiency and stability of the SCOSCs. Ultimately, the PM6‐D18‐b‐PYIT‐based device exhibits a power conversion efficiency (PCE) of 14.89%, which is the highest efficiency of the reported SCOSCs. Thanks to the aggregation restriction of each component and chain entanglement in the three‐in‐one system, the PM6‐D18‐b‐PYIT‐based SCOSC displays significantly higher stability than the corresponding two‐component (PM6‐D18:PYIT) and three‐component (PM6:D18:PYIT). These results demonstrate that the three‐in‐one strategy is facile and promising for developing SCOSCs with superior efficiency and stability.This article is protected by copyright. All rights reserved

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Covalently linked donor–acceptor dyad for efficient single material organic solar cells

Abstract: A novel covalently linked donor–acceptor dyad comprising a dithienopyrrol-based oligomeric donor and a fullerene acceptor was synthesized and characterized.

Cited by 34 publications

References 25 publications

Molecular Donor–Acceptor Dyads for Efficient Single‐Material Organic Solar Cells

Molecular Donor–Acceptor Dyads for Efficient Single‐Material Organic Solar Cells

Molecular Oligothiophene–Fullerene Dyad Reaching Over 5% Efficiency in Single‐Material Organic Solar Cells

Three‐in‐One Strategy Enables Single‐Component Organic Solar Cells with Record Efficiency and High Stability

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