A survey of electron-deficient pentacenes as acceptors in polymer bulk heterojunction solar cells

Suo, Ying; Lim, Yee‐Fun; Li, Zhong; Purushothaman, Balaji; Hallani, Rawad K.; Kim, Jo Eun; Parkin, Sean; Malliaras, George G.; Anthony, John E.

doi:10.1039/c0sc00433b

Cited by 124 publications

(79 citation statements)

References 40 publications

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“…29 This method avoids the use of highly toxic solvents such as carbon tetrachloride, and the high atominefficiency associated with brominating agents such as Nbromosuccinimide, reported in other procedures. 30,31 Treatment of 2 with sodium iodide eliminates bromine to produce the reactive intermediate dibromoquinodimethane, which combines with the commercial norbornadiene 3, to give an isomeric mixture of 2,9(10)-dinitro-6,13-dihydro-6,13-methanopentacene (4) in 50% yield. This was reduced in the presence of hydrazine and RANEY® nickel, to obtain the required 2,9(10)-diamino-6,13-dihydro-6,13-methanopentacene monomer (5) as a mixture of isomers.…”

Section: Polymer Synthesis and Characterizationmentioning

confidence: 99%

A highly rigid and gas selective methanopentacene-based polymer of intrinsic microporosity derived from Tröger's base polymerization

et al. 2018

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Polymers of intrinsic microporosity (PIMs) have been identified as potential next generation membrane materials for the separation of gas mixtures of industrial and environmental relevance. Based on the exceptionally rigid methanopentacene (MP) structural unit, a Polymer of Intrinsic Microporosity (PIM-MP-TB) was designed to demonstrate high selectivity for gas separations. PIM-MP-TB was prepared using PIMs, PIM-MP-TB is prepared in four simple steps from a cheap starting material.

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Section: Polymer Synthesis and Characterizationmentioning

confidence: 99%

A highly rigid and gas selective methanopentacene-based polymer of intrinsic microporosity derived from Tröger's base polymerization

et al. 2018

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“…Of particular relevance to this study is previous work by Shu and co-workers, who surveyed a variety of electron-deficient pentacenes as acceptors in BHJ devices with poly(3-hexylthiophene) [P3HT] acting as the donor material. 34 Pentacene-based small molecules are easily amenable to synthetic substitution, which makes them good candidates for comprehensive investigations (Figure 1). Device V OC and J SC were found to vary with the electron-withdrawing group and alkyl group substitution, respectively, and correlate with crystal structure packing motifs of the pentacene-based material.…”

Section: Introductionmentioning

confidence: 99%

“…The blend ratio simulated here is equivalent to that used in reported devices. 34 The chain length was 48 monomers, which corresponds to a molecular weight of about 8 kDa. Simulations of significantly longer chains, which would be more relevant to actual devices, were limited by computational feasibility.…”

Section: Introductionmentioning

confidence: 99%

“…Device V OC and J SC were found to vary with the electron-withdrawing group and alkyl group substitution, respectively, and correlate with crystal structure packing motifs of the pentacene-based material. 34 Here, we systematically evaluate, through a series of multi-scale molecular simulations, the structure-function relationships of these pentacene-based acceptors in P3HT to clarify how the chemical structure of the substituted pentacenes influences the blend morphology, which in In our molecular modeling approach, we perform atomistic molecular dynamics (MD)…”

Section: Introductionmentioning

confidence: 99%

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Dynamics, Miscibility, and Morphology in Polymer:Molecule Blends: The Impact of Chemical Functionality

Risko

Anthony

et al. 2015

Chem. Mater.

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Abstract.In the quest to improve the performance of organic bulk-heterojunction solar cells, many recent efforts have focused on developing molecular and polymer alternatives to commonly used fullerene acceptors. Here, molecular dynamics simulations are used to investigate polymer:molecule blends comprised of the polymer donor poly(3-hexylthiophene) (P3HT) with a series of acceptors based on trialkylsilylethynyl-substituted pentacene. A matrix of nine pentacene derivatives, consisting of systematic chemical variation both in the nature of the alkyl groups and electron-withdrawing moieties appended to the acene, is used to draw connections between the chemical structure of the acene acceptor and the nanoscale properties of the polymer:molecule blend, which include: polymer and molecular diffusivity, donor-acceptor packing and interfacial (contact) area, and miscibility. The results point to the very significant role that seemingly modest changes in chemical structure play during the formation of polymer:molecule blend morphologies.

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“…69 An impressive device performance of V OC = 1.10 V, J SC = 4 mA/cm 2 , FF = 0.4 and PCE = 1.7 % with P3HT as donor and Ba/Al as the cathode has been reported. 71 There are other types of non-fullerene electron acceptors such as polymer acceptors 68,72 , pentacenes 73 and graphene. 74 The research field of optoelectronic is growing so fast that new acceptor materials are emerging even as this thesis is being written and due to space and timeliness limitations, some of them have not been included.…”

Section: (4) Fluorenide Based Acceptorsmentioning

confidence: 99%

Novel materials for bulk heterojunction thin film organic photovoltaic devices - research and application

Gui¹

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The majority of organic semiconductors developed are more easily oxidized (p-type) than reduced (n-type). However, n-type organic semiconductors are important for a range of optoelectronic applications including organic photovoltaic devices, light-emitting diodes and field effect transistors (FETs). In spite of this there has been significantly less development of n-type compounds. This project focused on developing novel n-type semiconductors for use in organic photovoltaic devices.To identify the organic acceptor candidates, a series of novel materials were synthesized and characterized.Amongst these materials, 2-[(7-{9,9-di-n-propyl-9H-fluoren-2- K12 has the remarkable property in that it can be deposited from solution or by evaporation. K12exhibits a tendency to order in the solid state at room temperature, and with mild heating the process can be accelerated. The extent of ordering in the films was followed by Polarized OpticalMicroscopy, Atomic Force Microscopy, and Wide Angle X-ray Diffraction. K12 was found to be a good electron acceptor candidate for bulk heterojunction organic solar cells and as an active channel in organic field effect transistors (OFETs). A 0.7% power conversion efficiency under AM1.5 light was achieved in a bulk heterojunction solar cell configuration with poly(3-n-hexylthiophene) as the donor. The thermal properties of K12 enable the film morphology to be controlled at easily accessible temperatures allowing the charge mobility to be tuned over two orders of magnitude. The electron mobility in the films was found to be independent of the initial processing conditions (solution or evaporation). The electron mobility measured in a FET configuration was of order 10 -3 cm 2 /Vs for films prepared via either processing method whilst Photoinduced Charge Extraction in Linearly Increasing Voltage (PhotoCELIV) for annealed films gave a mobility of order 10 -4 cm 2 /Vs.To further tune the properties of K12 several chemical modifications were made. To harvest more of the solar spectrum derivatives with electron donating groups such as thiophene (K12-Th) and diphenylamine (K12-Diph) were prepared to extend the conjugation length and form a DonorAcceptor structure. Amongst the derivatives K12-Diph gave a greatly broadened absorption ranging between 200 nm and 800 nm. The dipole moment of K12 was found to play an important role in its morphology and hence K12b, which has a smaller dipole moment was prepared to investigate this effect further. It was found that the different dipole moments of K12 and K12b had dramatic effects on both the physical properties, reflected in their thermal properties and molecular packing. The morphological differences in films comprised of the each of the materials were observed to have a direct impact on the device performance in both OFET and OPV devices. The propensity of K12 to crystallize was found to give rise to better charge transport than K12b.Macromolecular structures K12-3 and K12-6 (with three and six K12 chromophores around a ii central benzene r...

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A survey of electron-deficient pentacenes as acceptors in polymer bulk heterojunction solar cells

Cited by 124 publications

References 40 publications

A highly rigid and gas selective methanopentacene-based polymer of intrinsic microporosity derived from Tröger's base polymerization

A highly rigid and gas selective methanopentacene-based polymer of intrinsic microporosity derived from Tröger's base polymerization

Dynamics, Miscibility, and Morphology in Polymer:Molecule Blends: The Impact of Chemical Functionality

Novel materials for bulk heterojunction thin film organic photovoltaic devices - research and application

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