Beyond efficiency: scalability of molecular donor materials for organic photovoltaics

Pò, Riccardo; Roncali, Jean

doi:10.1039/c5tc03740a

Cited by 123 publications

(110 citation statements)

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“…With the idea of increasing the scalability and limiting the economic cost and the environmental impact of the synthesis of organic materials for potential industrial application in OPV, Leriche and co‐workers from our group have developed the straightforward synthesis of DAD‐9 based on a central diiminofumaronitrile acceptor group (Scheme ). This compound was prepared in a few steps in good yield by double condensation of a TPA‐carbaldehyde derivative with 2,3‐diaminomaleonitrile under microwave activation with trifluoroacetic acid as catalyst .…”

Section: Tpa‐based Push–pull Molecular Donors For Organic Photovoltaicsmentioning

confidence: 99%

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Blanchard

Malacrida

Cabanetos

et al. 2018

Polymer International

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This review article gives an overview of past and current activities in the Linear Conjugated Systems Group of Angers and in the IPOC – Functional Polymers Group of the Institute of Polymer Chemistry of Stuttgart on the use of triphenylamine (TPA) as versatile building block for organic electronics. In the first part, the properties of TPA itself are introduced including geometrical and energy level considerations. Dimerization of TPA to tetraphenylbenzidine upon electrochemical oxidation is highlighted. The blocking of TPA para‐positions and its implications in terms of electroactivity is further discussed. The second part shows that dimerization of TPA as pendant redox‐active moieties in polymers is a versatile strategy to crosslink polymer films. Coming from redox homopolymers the crosslinking strategy is extended towards conjugated redox polymers based on polythiophenes and block copolymers. Conductivity mechanisms and the influence of doping level on conductivity are probed with cyclic voltammetry coupled with in situ conductance and four‐point probe measurements. The last part is dedicated to the use of TPA as an electron‐donating block in the design of donor‐π‐acceptor chromophores and their use as active material in organic photovoltaics. An overview of some relevant TPA‐based push–pull molecules from the literature and our contribution to this field is presented emphasizing the progress of the photovoltaic performance of organic solar cells made over the last decade. © 2018 Society of Chemical Industry

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Section: Tpa‐based Push–pull Molecular Donors For Organic Photovoltaicsmentioning

confidence: 99%

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Blanchard

Malacrida

Cabanetos

et al. 2018

Polymer International

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“…The 2,6-dialkoxyphenyl groups at meso-10,20-positions of porphyrins appear to be the rule of thumb since the first introduction of such groups in porphyrin dye YD2-o-C8 for its wrapping ability to retard the intermolecular aggregation and back electron transfer. 21 Nevertheless, implantation of 2,6-dialkoxyphenyl simultaneously introduces disadvantages such as synthetic complexity 38,39 and utilization of hazardous chemicals, e.g., n-butyllithium, which largely limits large-scale dye synthesis and potential industrial application. With substituted bulkier amine, dye WW-5 with meso-10,20-functionalized mesityl groups exhibits promising conversion efficiency of 10.3% (V OC = 0.766 V; J SC = 18.43 mA cm -2 ) comparable to WW-6 with conversion efficiency of 10.5% (V OC = 0.809 V; J SC = 17.69 mA cm -2 ) which is functionalized with 2,6-dialkoxylphenyl groups.…”

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A feasible scalable porphyrin dye for dye-sensitized solar cells under one sun and dim light environments

Liu

Chou

et al. 2016

J. Mater. Chem. A

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We have devised new porphyrin dye Y1A1 for photovoltaic application under both light sources of AM1.5G standard condition and low light intensity at 300 ~ 2400 lux. The dye Y1A1 tailored with two 3,5-di-tert-butyl-4-methoxyphenyl groups at meso-10,20-positions which helps the solubility of the molecule in solvents and avoids involvement of the hazardous chemical n-butyllithium during the synthesis of some typical high efficiency porphyrins such as YD2-o-C8 and LD-series dyes. The dye is also structurally simple so that large-scale synthesis for future industrial application becomes feasible. The Y1A1-based cells were found to exhibit higher performance using I -/I 3 rather than Co 2+/3+ electrolyte in the presence of CDCA co-adsorbent. Addition of Li + together with removal of GuSCN as electrolyte additives benefit the performance in terms of higher capacitance at compensate of surface charge recombination and electron lifetime. The optimized cells based on Y1A1 showed a power conversion efficiency of 9.22% at AM1.5G condition and as high as 19.5%illuminated under 350 lux of LED light. IntroductionSolar cells are well-known technologies in terms of converting energy from sun to a flow of electrons. To provide a controllable and comparable testing condition for solar cells, standard 1 Sun condition (100 mW cm -2 ) is generally equipped in the laboratory for mimicking the outdoor environments which typically shed lights with intensity of >100,000 lux. In contrast, indoor lights surrounding the living places of the community can be considered as low light or dim light due to relatively lower photon flux. These places including homes, schools, offices, factories, hospitals and stores require brightness of light sources typically ranging between 300~500 lux. Higher light level demand for specific area such as laboratories, reading rooms, production halls, first aids and show rooms require the illuminated light of 500~1500 lux. With the thriving concept of indoor energy-harvesting aiming at these reachable light sources, dye-sensitized solar cells (DSCs) are certainly one of the most promising light-to-electricity conversion technologies. 1 DSCs have drawn growing attention since the pioneer work initiated by Grätzel's groups. 2 In the past two decades, molecular engineering of dyes yields several kinds of molecular architectures for efficient solar-to-electricity conversion. 3, 4 These high performance dyes includes the ruthenium polypyridyl complexes, 5, 6 the arylamine-based organic dyes 7-12 and the porphyrin-based dyes. 13-15 Graphical AbstractA new porphyrin dye Y1A1 has been devised for high performance dye-sensitized solar cells under the irradiance of either AM1.5G simulated sunlight or fluorescent/LED based dim light.

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“…[131][132][133][134] Although these questions deserve specific research efforts, economic considerations cannot be the exclusive motivation of research and the multiple fundamental problems still posed by the physics of OPV and by the chemistry of active materials clearly require a continuation of research effort. The "OPV paradox" is that the continuous increase of PCE does not open the door to industrialization but on the contrary tend to relegate OPV into a purely academic topic.…”

Section: ) Connection Of D and A: The Linker L Connecting D And Amentioning

confidence: 99%

The Dawn of Single Material Organic Solar Cells

2018

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Single material organic solar cells (SMOSCs) are based on ambivalent materials containing electron donor (D) and acceptor (A) units capable to ensure the basic functions of light absorption, exciton dissociation, and charge transport. Compared to bicomponent bulk heterojunctions, SMOSCs present several major advantages such as considerable simplification of cell fabrication and a strong stabilization of the morphology of the D/A interface, and thus of the cell lifetime. In addition to these technical issues, SMOSCs pose fundamental questions regarding the possible formation, and dissociation of excitons on the same molecular D–A architecture. SMOSCs are developed with various approaches, namely “double‐cable” polymers, block copolymers, oligomers, and molecules that differ by the donor platform: polymer or molecule, the nature of A, the D–A connection, and the intra‐ and intermolecular interactions of D and A. Although for several years the maximum efficiency of SMOSCs has remained limited to 1.0–1.5%, impressive progress has been recently accomplished leading to SMOSCs with 4.0–5.0% efficiency. Here, recent advances in the synthesis of D–A materials for SMOSCs are presented in the broader context of the chemistry of organic photovoltaic materials in order to discuss possible directions for future research.

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Beyond efficiency: scalability of molecular donor materials for organic photovoltaics

Abstract: The preparation of various molecules taken as representative examples of some of the main classes of molecular donors for organic solar cells is discussed in order to assess the complexity and possibilities of scaling-up their synthesis.

Cited by 123 publications

References 86 publications

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications

A feasible scalable porphyrin dye for dye-sensitized solar cells under one sun and dim light environments

The Dawn of Single Material Organic Solar Cells

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