An Air‐Stable Low‐Bandgap n‐Type Organic Polymer Semiconductor Exhibiting Selective Solubility in Perfluorinated Solvents

Takeda, Yoshifumi; Andrew, Trisha L.; Lobez, Jose M.; Mork, A. Jolene; Swager, Timothy M.

doi:10.1002/anie.201204066

Cited by 76 publications

(48 citation statements)

References 68 publications

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“…Polymer semiconductors are receiving considerable attention in fundamental science and applied research owing to their potential for application in various electronic devices, [1,2] such as organic thin-film transistors (OTFTs) [3][4][5] and polymer solar cells (PSCs). [6,7] In the last decade,agreat number of ptype polymers with promising OTFT [2,8] and PSC [9,10] performance have been synthesized.…”

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confidence: 99%

Effects of Bithiophene Imide Fusion on the Device Performance of Organic Thin‐Film Transistors and All‐Polymer Solar Cells

Wang,

Yan,

Guo

et al. 2017

Angew Chem Int Ed

156

106

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Two new bithiophene imide (BTI)-based n-type polymers were synthesized. f-BTI2-FT based on a fused BTI dimer showed a smaller band gap, a lower LUMO, and higher crystallinity than s-BTI2-FT containing a BTI dimer connected through a single bond. s-BTI2-FT exhibited a remarkable electron mobility of 0.82 cm V s , and f-BTI2-FT showed a further improved mobility of 1.13 cm V s in transistors. When blended with the polymer donor PTB7-Th, f-BTI2-FT-based all-polymer solar cells (all-PSCs) attained a PCE of 6.85 %, the highest value for an all-PSC not based on naphthalene (or perylene) diimide polymer acceptors. However, s-BTI2-FT all-PSCs showed nearly no photovoltaic effect. The results demonstrate that f-BTI2-FT is one of most promising n-type polymers and that ring fusion offers an effective approach for designing polymers with improved electrical properties.

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confidence: 99%

Effects of Bithiophene Imide Fusion on the Device Performance of Organic Thin‐Film Transistors and All‐Polymer Solar Cells

Wang,

Yan,

Guo

et al. 2017

Angew Chem Int Ed

156

106

View full text Add to dashboard Cite

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“…In addition, the strong electronegativity might induce F-S and F-H interactions and potentially modifies the molecular conformation and intermolecular organization (6). Furthermore, it has been shown that fluorination often leads to enhanced thermal and oxidative stability (9)(10)(11). Given a combination of these desirable properties, fluorine-containing CPs have led to most of the best-performing polymer-based solar cells to date (12)(13)(14)(15).…”

mentioning

confidence: 99%

Impact of backbone fluorination on nanoscale morphology and excitonic coupling in polythiophenes

Haws

Fei

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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Fluorination represents an important strategy in developing highperformance conjugated polymers for photovoltaic applications. Here, we use regioregular poly(3-ethylhexylthiophene) (P3EHT) and poly(3-ethylhexyl-4-fluorothiophene) (F-P3EHT) as simplified model materials, using single-molecule/aggregate spectroscopy and molecular dynamic simulations, to elucidate the impacts of backbone fluorination on morphology and excitonic coupling on the molecular scale. Despite its high regioregularity, regioregular P3EHT exhibits a rather broad distribution in polymer chain conformation due to the strong steric hindrance of bulky ethylhexyl side chains. This conformational variability results in disordered interchain morphology even between a few chains, prohibiting long-range effective interchain coupling. In stark contrast, the experimental and molecular dynamic calculations reveal that backbone fluorination of F-P3EHT leads to an extended rod-like single-chain conformation and hence highly ordered interchain packing in aggregates. Surprisingly, the ordered and close interchain packing in F-P3EHT does not lead to strong excitonic coupling between the chains but rather to dominant intrachain excitonic coupling that greatly reduces the molecular energetic heterogeneity.fluorinated polythiophenes | photophysics | single-molecule spectroscopy | morphology | organic electronics M orphology and excitonic coupling are among the most important factors dictating the functions and performance of conjugated polymers (CPs) in a variety of optoelectronic applications (1-4). To tune and optimize the morphological and optoelectronic properties of CPs, chemical structure modification of the backbone and side chains is one of the main and most effective approaches (5-7). It has been revealed that the position, size, and length of side chains dramatically affect the morphology and optoelectronic properties of CPs. In the efforts to develop high-performance photovoltaic CPs, the introduction of fluorine atoms onto aromatic comonomers, i.e., the fluorination of polymer backbone, offers a very appealing strategy to tune the electronic properties, morphology, and photochemical stability (6-8). It is proposed that the inherent electronwithdrawing nature of fluorine atoms lowers the highest energy occupied molecular orbital energy levels, thereby increasing the open-circuit voltage in photovoltaics. In addition, the strong electronegativity might induce F-S and F-H interactions and potentially modifies the molecular conformation and intermolecular organization (6). Furthermore, it has been shown that fluorination often leads to enhanced thermal and oxidative stability (9-11). Given a combination of these desirable properties, fluorine-containing CPs have led to most of the best-performing polymer-based solar cells to date (12-15).For typical CPs, the primarily created exciton is Coulombically bound upon photoexcitation mainly due to the low dielectric constant and strong electron-phonon interaction in polymers. The interchain and intrachain morp...

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“…On the contrary, F atom can significantly enhance the non‐covalent interactions through F‐F, F‐C, F‐O, F‐S or F‐H etc. among the molecules . Such interactions can push F‐containing molecules more closely packed and facilitate effective energy transfer and charge transport in the films .…”

Section: Methodsmentioning

confidence: 99%

Impact of Fluorine Atoms on Perylene Diimide Derivative for Fullerene‐Free Organic Photovoltaics

Zhao

Sun

Liu

et al. 2017

Chemistry An Asian Journal

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The incorporation of fluorine atoms in organic semiconducting materials has attracted much attention recently due to its unique function to manipulate the molecular packing, film morphology and molecular energy levels. In this work, two perylenediimide (PDI) derivatives FPDI-CDTph and FPDI-CDTph2F were designed and synthesized to investigate the impact of fluorination on non-fullerene acceptors. Both FPDI-CDTph and FPDI-CDTph2F exhibited strong and broad absorption profiles, suitable lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) energy levels, and good electron transport ability. Compared with FPDI-CDTph, the fluorinated acceptor (FPDI-CDTph2F) afforded an optimal bulk heterojunction morphology with an interconnected and nanoscale phase separated structure that allowed more efficient exciton dissociation and balanced charge transport. Consequently, organic solar cells based on FPDI-CDTph2F showed a much higher power conversion efficiency (PCE) of 6.03 % than that of FPDI-CDTph based devices (4.10 %) without any post-fabrication treatment.

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An Air‐Stable Low‐Bandgap n‐Type Organic Polymer Semiconductor Exhibiting Selective Solubility in Perfluorinated Solvents

Cited by 76 publications

References 68 publications

Effects of Bithiophene Imide Fusion on the Device Performance of Organic Thin‐Film Transistors and All‐Polymer Solar Cells

Effects of Bithiophene Imide Fusion on the Device Performance of Organic Thin‐Film Transistors and All‐Polymer Solar Cells

Impact of backbone fluorination on nanoscale morphology and excitonic coupling in polythiophenes

Impact of Fluorine Atoms on Perylene Diimide Derivative for Fullerene‐Free Organic Photovoltaics

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