Isoindigo fluorination to enhance photovoltaic performance of donor–acceptor conjugated copolymers

Yang, Yuchong; Wü, Ray; Wang, Xin; Xu, Xiaopeng; Li, Zuojia; Li, Kai; Peng, Qiang

doi:10.1039/c3cc47677d

Cited by 77 publications

(88 citation statements)

References 27 publications

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“…The incorporation of halogen atoms to a nal isoindigo material is not a foreign concept, with both uorinated [64][65][66] and chlorinated 67 derivatives reported in the literature. Fluorination is by far the most popular, highlighted by several publications within the last few years, but requires a uorinated precursor to the base isoindigo core.…”

Section: Materials Synthesismentioning

confidence: 99%

The structural evolution of an isoindigo-based non-fullerene acceptor for use in organic photovoltaics

et al. 2015

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The structural evolution of a functional isoindigo-based non-fullerene acceptor led to the development of three new materials to address the deficiencies of the original framework. Owing to the versatility of the structure and the flexibility of the synthetic procedures, these three new materials were accessible from previously optimized reaction conditions and similar precursor materials. The influence of structural modification on the optical, electrochemical and thermal properties were assessed and correlated with DFT calculations to provide compelling evidence for the effect of each substitution and how they relate to each particular adaptation. The structure-property relationships were investigated for their photovoltaic performance in solution processable BHJ devices fabricated in inverted architectures. Evaluation of device performance demonstrated that a single modification did not improve on the efficiency of the original structure, but the combination of both induced nonplanarity, and increased electron affinity of the fourth iteration showed the potential of our framework, with PCE reaching 1.9%.

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Section: Materials Synthesismentioning

confidence: 99%

The structural evolution of an isoindigo-based non-fullerene acceptor for use in organic photovoltaics

et al. 2015

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“…By introducing fluorine atoms into the IID unit, P75-based devices with a thin conjugated polyelectrolyte interfacial layer achieved an impressively high PCE of 7.04 % in an inverted device configuration [75].…”

Section: Iid-containing D-a Polymersmentioning

confidence: 99%

Donor Materials for Organic Solar Cell (OSC)

Song

2014

Organic and Hybrid Solar Cells

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In the past 10 years, the highest efficiency obtained from organic photovoltaics (OPVs), such as bulk heterojunction (BHJ) polymer solar cells (PSCs), has risen from 2.5 to 11 %, while the solution-processed small molecule (SM) BHJ solar cells arrived at competitive level of 10 %. This rapid progress was achieved by the development of both materials synthesis and device fabrication. With the better understanding of the mechanism of the photon-to-electron conversion process in OPV, the commercialization of PSCs could be realized soon. Nowadays, a lot of efforts have been devoted to developing of new donor, acceptor, and interfacial layer materials, optimizing nanostructures of the active layer, fabricating new device architectures, and so on.The development of new donor materials for PSCs is one of the most popular research topics in the field of PSCs and many excellent results have been published. A variety of polymers and SMs have been reported as donor materials for OPVs and some of them might be candidates for the commercialization later. From the reported structures, the conjugated backbones of polymers for OPV can be arbitrarily classified into a few categories based on the constitution of the repeating unit, namely, (a) homopolymers, (b) donor-acceptor polymers, (c) quinoid polymers, and (d) other types of polymers; whereas the SM donors can be classified into the following categories based on their main structures, (a) donor-acceptor type molecules, (b) squaraine dyes, and (c) oligomer and dendrimers.

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“…The isoindigo core contains two fused lactam rings, inducing a strong electron-deficient character and, therefore, rendering it attractive as an acceptor component in push-pull type organic semiconductors. Nowadays, isoindigo has become a widely applied building block, with over 100 publications on its characteristics and use in polymer and molecular solar cells [35][36][37][38][39][40][41]. Power conversion efficiencies (PCE's) of 3.7 and 7.3%, respectively, have been reached for small molecule and polymer solar cells based on photoactive isoindigo-containing light-harvesting materials [40,41].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of N,N′-dialkyl-6,6′-dibromoisoindigo Derivatives by Continuous Flow

Maes¹,

Pirotte²,

Brebels³

et al. 2015

J Flow Chem

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In this work, the synthesis of N,N′-dialkyl-6,6′-dibromoisoindigo derivatives by continuous-flow chemistry is explored as a means to enhance material availability and structural diversity, in particular toward the application of isoindigo-based semiconductors in high-performance organic photovoltaic devices. The individual steps in the conventional batch synthesis protocol are evaluated and, when needed, adapted to flow reactors. To overcome the low solubility of nonalkylated 6,6′-dibromoisoindigo in common organic solvents, the flow condensation reaction between the 6-bromo-isatin and 6-bromo-oxindole precursors is evaluated in polar aprotic solvents. Dialkylation of 6,6′-dibromoisoindigo is readily performed in flow using a solid-phase reactor packed with potassium carbonate. In an alternative strategy, solubility is ensured by first introducing the N-alkyl side chains on 6-bromo-isatin and 6-bromo-oxindole (accessible via a highyielding flow reduction of alkylated 6-bromo-isatin), followed by condensation using the conventional method in acetichydrochloric acid medium. The N,N′-dialkylated 6,6′-dibromoisoindigo derivatives indeed show enhanced solubility in the hot reaction mixture compared to the non-alkylated material but eventually precipitate when the reaction mixture is cooled down. Nevertheless, the condensation between both alkylated starting materials is achieved in flow without any blockages by keeping the outlet from the reactor heated and as short as possible. The latter strategy allows the preparation of both symmetrically and asymmetrically N-substituted isoindigo compounds.

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Isoindigo fluorination to enhance photovoltaic performance of donor–acceptor conjugated copolymers

Cited by 77 publications

References 27 publications

The structural evolution of an isoindigo-based non-fullerene acceptor for use in organic photovoltaics

The structural evolution of an isoindigo-based non-fullerene acceptor for use in organic photovoltaics

Donor Materials for Organic Solar Cell (OSC)

Synthesis of N,N′-dialkyl-6,6′-dibromoisoindigo Derivatives by Continuous Flow

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