Bis-Azide Low-Band Gap Cross-Linkable Molecule N3-[CPDT(FBTTh2)2] to Fully Thermally Stabilize Organic Solar Cells Based on P3HT:PC61BM

Awada, Hussein; Gorisse, Thérèse; Peresutti, Romain; Tjoutis, Thomas; Moreau, Joël J. E.; Wantz, Guillaume; Dautel, Olivier

doi:10.1021/acsomega.6b00476

Cited by 13 publications

(13 citation statements)

References 47 publications

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“…In polymer:fullerene systems, due to spherical structure of fullerenes, excessive aggregation of fullerene molecules upon heating at relatively high temperature eventually leads to large‐scale phase separation with sharply reduced photovoltaic performance. There are various strategies to solve the above problem, such as usage of nonfullerene or fullerene derivative acceptors, molecular design by introducing rigid groups in side chains for conjugated polymers, crosslinking of donor or acceptor by polymerization, diazotization or other reactions, incorporation of third additives via supramolecular interactions, interfacial compatibilization, molecular lock of polymer, removal of high‐boiling point solvent additives, etc.…”

Section: Introductionmentioning

confidence: 99%

Improved Glass Transition Temperature towards Thermal Stability via Thiols Solvent Additive versus DIO in Polymer Solar Cells

Yin

Zhou

Zhang

et al. 2017

Macromol. Rapid Commun.

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The halogen-free solvent additive, 1,4-butanedithiol (BT) has been incorporated into PTB7-Th:PC BM, leading to higher power conversion efficiency (PCE) value as well as substantially enhanced thermal stability, as compared with the traditional 1,8-diiodooctane (DIO) additive. More importantly, the improved thermal stability after processing with BT contributes to a higher glass transition temperature (T ) of PTB7-Th, as determined by dynamic mechanical analysis. After thermal annealing at 130 °C in nitrogen atmosphere for 30 min, the PCE of the specimen processed with BT reduces from 9.3% to 7.1%, approaching to 80% of its original value. In contrast, the PCE of specimens processed with DIO seriously depresses from 8.3% to 3.8%. These findings demonstrate that smart utilization of low-boiling-point solvent additive is an effective and practical strategy to overcome thermal instability of organic solar cells via enhancing the T of donor polymer.

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Section: Introductionmentioning

confidence: 99%

Improved Glass Transition Temperature towards Thermal Stability via Thiols Solvent Additive versus DIO in Polymer Solar Cells

Yin

Zhou

Zhang

et al. 2017

Macromol. Rapid Commun.

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“…This bisazide has a wide absorption range and can harvest additional solar light in addition to stabilizing the BHJ morphology. In contrast to other existing azide crosslinkers, full retention of the PCE after curing and aggressive thermal ageing at 150 • C for 24 h could be achieved at a ratio of 1:0.2:1 (P3HT:linker:PC 61 BM) [62]. However, residual unreacted hydroxy precursor contained in the target compound might have had an additional effect on this remarkable result.…”

Section: Small Molecule Azide Crosslinkersmentioning

confidence: 89%

Reactive & Efficient: Organic Azides as Cross-Linkers in Material Sciences

Schock

Bräse

2020

Molecules

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The exceptional reactivity of the azide group makes organic azides a highly versatile family of compounds in chemistry and the material sciences. One of the most prominent reactions employing organic azides is the regioselective copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition with alkynes yielding 1,2,3-triazoles. Other named reactions include the Staudinger reduction, the aza-Wittig reaction, and the Curtius rearrangement. The popularity of organic azides in material sciences is mostly based on their propensity to release nitrogen by thermal activation or photolysis. On the one hand, this scission reaction is accompanied with a considerable output of energy, making them interesting as highly energetic materials. On the other hand, it produces highly reactive nitrenes that show extraordinary efficiency in polymer crosslinking, a process used to alter the physical properties of polymers and to boost efficiencies of polymer-based devices such as membrane fuel cells, organic solar cells (OSCs), light-emitting diodes (LEDs), and organic field-effect transistors (OFETs). Thermosets are also suitable application areas. In most cases, organic azides with multiple azide functions are employed which can either be small molecules or oligo- and polymers. This review focuses on nitrene-based applications of multivalent organic azides in the material and life sciences.

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“…Likewise, a lot of efforts went into the design of cross‐linkable materials to lock the as‐cast morphology in‐between donors, acceptors, or between both species. Cross‐linking was either accomplished by structural modification of the donor and/or acceptor side‐groups or by incorporating third‐component cross‐linkers . The latter were designed mostly around vinyl and azide functional groups to cross‐link the bulk‐heterojunction components.…”

Section: Introductionmentioning

confidence: 99%

“…Cross‐linking was either accomplished by structural modification of the donor and/or acceptor side‐groups or by incorporating third‐component cross‐linkers . The latter were designed mostly around vinyl and azide functional groups to cross‐link the bulk‐heterojunction components. Azide cross‐linkers are of particular interest, because the cross‐linking reaction with the bulk‐heterojunction components can be triggered by either UV light or temperature …”

Section: Introductionmentioning

confidence: 99%

Thermal Stabilization of the Bulk‐Heterojunction Morphology in Polymer:Fullerene Solar Cells Using a Bisazide Cross‐Linker

et al. 2018

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After enhancing the power conversion efficiencies of organic solar cells beyond 10%, their long term stability has become the most urgent challenge in order to eventually integrate organic solar cells into end‐user products. Solar devices may have to endure harsh conditions already during their fabrication, typically requiring lamination temperatures up to 120 °C, critical for the initial performance of organic solar cells. In this work, polymer:fullerene bulk‐heterojunctions are fabricated with significantly enhanced thermal stability at 120 °C and beyond, by locking the bulk‐heterojunction morphology through incorporating the novel cross‐linkable bisazide 1,2‐bis((4‐(azidomethyl)phenethyl)thio)ethane (TBA‐X). Bulk‐heterojunctions comprising various light‐harvesting polymers and the industrially relevant fullerene acceptor PC61BM are investigated. Upon thermal annealing, the reference blends without the cross‐linking TBA‐X exhibit only moderate thermal stability and a relative loss of more than 70% of their initial performance, mainly originating from aggregation of the fullerene. In contrast, polymer:fullerene blends comprising TBA‐X retain up to 90% of their initial performance despite the harsh thermal annealing at 120 °C for up to 200 h.

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Bis-Azide Low-Band Gap Cross-Linkable Molecule N₃-[CPDT(FBTTh₂)₂] to Fully Thermally Stabilize Organic Solar Cells Based on P3HT:PC₆₁BM

Cited by 13 publications

References 47 publications

Improved Glass Transition Temperature towards Thermal Stability via Thiols Solvent Additive versus DIO in Polymer Solar Cells

Improved Glass Transition Temperature towards Thermal Stability via Thiols Solvent Additive versus DIO in Polymer Solar Cells

Reactive & Efficient: Organic Azides as Cross-Linkers in Material Sciences

Thermal Stabilization of the Bulk‐Heterojunction Morphology in Polymer:Fullerene Solar Cells Using a Bisazide Cross‐Linker

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