Diketopyrrolopyrrole-based conjugated polymers and small molecules for organic ambipolar transistors and solar cells

Naik, Mallari A.; Patil, Satish

doi:10.1002/pola.26843

Cited by 90 publications

(100 citation statements)

References 135 publications

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“…A subsequent condensation reaction and concurrent deprotection of the tetrahydropyranyl groups affords the 2,9-dihydroxy-7,14-di(thiophen-2-yl)-diindolo[3,2,1-de:3′,2′,1′-ij] [1,5]naphthyridine-6,13-dione (INDT) compound 7. This compound was then alkylated with 2-octyldodecyl chains to improve solubility and then subsequently brominated with N-bromosuccinimide to afford our novel INDT monomer 9.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…When half of this solution was added, the reaction turned deep green; once addition was complete, the reaction was a dark green/blue color. After addition, the reaction was covered and allowed to warm to room temperature and stirred for 24 h. The solid was then collected by vacuum filtration and washed with methanol until washings ran colorless to give a blue solid [1,5]naphthyridine-6,13-dione. (E)-5,5′-Bis((tetrahydro-2H-pyran-2-yl)oxy)-[2,2′-biindolinylidene]-3,3′-dione (2.2 g, 4.8 mmol), and 2-(thiophen-2-yl)acetyl chloride (3.6 mL, 29 mmol) were dissolved in anhydrous xylene (96 mL), and the reaction refluxed at 165°C for 24 h. The blue reaction turned purple after 1 h. After 24 h the vapors from the argon flow were no longer acidic.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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A Nature-Inspired Conjugated Polymer for High Performance Transistors and Solar Cells

et al. 2015

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A novel, highly soluble chromophore for use in organic electronics based on an indigoid structure is reported. Copolymerization with thiophene affords an extremely narrow band gap polymer with a maximum absorption at ∼800 nm. The novel polymer exhibits high crystallinity and high ambipolar transport in OFET devices of 0.23 cm 2 V −1 s −1 for holes and 0.48 cm 2 V −1 s −1 for electrons. OPV device efficiencies up to 2.35% with light absorbance up to 950 nm demonstrate the potential for this novel chromophore in near-IR photovoltaics. ■ INTRODUCTIONThe development of novel organic conjugated polymers has gained momentum in recent times due to their possible applications in organic photovoltaic (OPV) and organic fieldeffect transistor (OFET) devices where their lower cost, light weight, and mechanical flexibility are all attractive properties. Current high performance polymers have enabled OFET devices with mobilities in excess of 2 cm 2 V −1 s −1 and OPV devices with power conversion efficiencies (PCEs) of over 8%. 1−3 Ultra-narrow band gap conjugated polymers are of great interest due to the ease of charge injection when incorporated into ambipolar OFETs and also their near-IR optical absorption for use in both tandem and transparent OPV devices. 4 Considerable interest has focused on planar bis-lactam containing polymers such as diketopyrrolopyrrole (DPP, 1) 5 and isoindigo (2). 6 The electron withdrawing nature of the lactam core alongside its planarity has enabled DPP and isoindigo containing conjugated polymers to reach both OPV PCEs and OFET mobilities.Indigo (3) is the most produced natural dye worldwide and has a highly planar structure arising from intramolecular hydrogen bonding between the oxygen and the amide protons of the indol-3-one units. 7 Upon photoexcitation, rotation about the central carbon−carbon bond can effect trans−cis isomerization 8 as well as either single or double proton transfer, resulting in rapid energy loss through internal conversion, thereby negating any potential for OPV devices. 9 As a semiconductor in OFET devices, indigo has shown hole mobilities up to 1 × 10 −2 cm 2 V −1 s −1 . 10 More recently, functionalized indigoids have been investigated, and the mobility can be slightly enhanced to 1.3 × 10 −2 cm 2 V −1 s −1 using 5,5′-dichloroindigo. 11 Crucially, the use of naturally occurring compounds as building blocks for materials in organic electronics can begin to address the issues of sustainability associated with them. As an example, Cibalackrot (7,14-diphenyldiindolo[3,2,1-de:3′,2′,1′-ij][1,5]naphthyridine-6,13-dione, INDP) is an indigo derivative first synthesized in Figure 1. Bis-lactam containing compounds and polymer building blocks. Article pubs.acs.org/Macromolecules

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

A Nature-Inspired Conjugated Polymer for High Performance Transistors and Solar Cells

et al. 2015

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“…1a). Similarly, another representative electron-accepting unit, diketopyrrolopyrrole (DPP) [8][9][10], can be regarded as butadiene moiety connected by electron-donating nitrogen atoms as well as electron-withdrawing C=O bonds (Fig. 1b).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Azole-fused Benzothiadiazoles as Key Units for Functional π-Conjugated Compounds

Nakamura

Okazaki

Arakawa

et al. 2017

J. Photopol. Sci. Technol.

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2,1,3-Benzothiadiazole (BT) is a widely used electron-accepting unit in organic electronics including organic solar cells (OSCs). As modifications of BT skeleton, two types of azolefused BT units were designed and synthesized; thiazole-fused BT with an electronwithdrawing C=N bond and imidazole-fused BT with an electron-donating nitrogen atom as well as an electron-withdrawing C=N bond. Electrochemical measurements and theoretical calculations suggest that thiazole-fusion enhances the electron-accepting ability, whereas imidazole-fusion endows the BT skeleton with electron-donating ability while maintaining its electron-accepting ability. Moreover, in thiazole-fused BT units, the electronic structure could be further modulated by varying the oxidation state of the sulfur atom in methylthio group at the fused thiazole ring.

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“…DPP was selected as the core moiety for this study in view of its convenient synthesis, excellent light absorption properties, good photochemical/thermal stability, and excellent charge carrier mobility. [9][10][11][12] We have further functionalized the DPP core with electron-withdrawing aldehyde (DPP-BZ), cyanoacrylic ester (DPP-ES), and cyanoacrylic amide (DPP-AM) units ( Fig. 1) in an effort to tune the optical and redox properties of the DPP core.…”

Section: Introductionmentioning

confidence: 99%

Organic solar cells based on acceptor-functionalized diketopyrrolopyrrole derivatives

et al. 2015

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Abstract. The synthesis and characterization of three solution processable diketopyrrolopyrrole (DPP) derivatives featuring acceptor units attached to the core by alkyne linker units is reported. Cyclic voltammetry and density functional theory calculations indicate that the DPP derivatives possess similar HOMO and LUMO energies. Solar cells were fabricated by blending the synthesized DPP derivatives with [6,6]-phenyl-C71-butyrate methyl ester. The influence of donor: acceptor blend ratio, film thickness, annealing temperature, and annealing time on device performance was studied. Differences in device performance were related to atomic force microscopy measurements of the films. The highest power conversion efficiency of 1.76% was achieved for the DPP derivative functionalized with an aldehyde electron-withdrawing group with a 1∶0.7 donor:acceptor ratio when the active layer was annealed for 10 min at 110°C.

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Diketopyrrolopyrrole-based conjugated polymers and small molecules for organic ambipolar transistors and solar cells

Cited by 90 publications

References 135 publications

A Nature-Inspired Conjugated Polymer for High Performance Transistors and Solar Cells

A Nature-Inspired Conjugated Polymer for High Performance Transistors and Solar Cells

Synthesis of Azole-fused Benzothiadiazoles as Key Units for Functional π-Conjugated Compounds

Organic solar cells based on acceptor-functionalized diketopyrrolopyrrole derivatives

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