Article
Chemistry, Organic
Seihou Jinnai, Ayumi Oi, Takuji Seo, Taichi Moriyama, Ryunosuke Minami, Suguru Higashida, Yutaka Ie
Summary: By incorporating cyano-substituted naphthobisthiadiazole units into π-conjugated systems, the researchers synthesized an electron-accepting compound CNNTz-TR, which showed a low-lying energy level due to the presence of cyano groups. The results demonstrated that embedding the CNNTz unit into the π-conjugated backbone is an effective strategy for designing electron-accepting semiconducting materials with improved performance in organic solar cells.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Yuichi Tsuchii, Taiki Menda, Sunbin Hwang, Takuma Yasuda
Summary: Pi-Conjugated polymers P(BDT-BTI) and P(BDT-BTA) were designed and synthesized for organic photovoltaics. The introduction of electron-withdrawing moieties lowered the energy levels and increased the open-circuit voltages of the devices. Blending P(BDT-BTA) with IT-4F resulted in high crystallinity and retained pi-pi stacking interactions, leading to power conversion efficiencies as high as 9.6% without any additives or post-treatments.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2023)
Article
Materials Science, Multidisciplinary
Dukhan Kim, Emily A. Mueller, Da Seul Yang, Danielle E. Fagnani, Jinsang Kim, Anne J. McNeil
Summary: This study demonstrates that a single copolymer containing a conjugated poly(3-hexylthiophene) backbone and fullerene-functionalized side chains can serve as a general blend stabilizer, suppressing phase separation in multiple conjugated polymer/fullerene thin film blends as well as in a photovoltaic device.
ACS APPLIED POLYMER MATERIALS
(2021)
Article
Materials Science, Multidisciplinary
Mingpeng Li, Zhixiang Li, Guangkun Song, Changzun Jiang, Xin Chen, Jian Wang, Yang Yang, Xiangjian Wan, Chenxi Li, Yongsheng Chen
Summary: In this study, three non-fullerene acceptors (NFAs) with different end groups (F'-2Cl, F'-NCl, and F'-N2Cl) were designed and synthesized to investigate the impact of molecular structures and morphologies on the photovoltaic properties and energy loss of organic solar cells (OSCs). It was found that the PM6:F'-N2Cl based OSC exhibited a favorable morphology and achieved the highest power conversion efficiency (PCE) of 14.13% with a J(sc) of 20.31 mA cm(-2), a V-oc of 0.927 V, and a FF of 74.68%. Moreover, extending the conjugation of the end group led to a narrower molecular bandgap and lower energy loss in F'-NCl and F'-N2Cl based devices. This work provides an efficient strategy to optimize the molecular structures of non-fullerene acceptors and improve the properties of OSCs.
JOURNAL OF MATERIALS CHEMISTRY C
(2023)
Article
Chemistry, Multidisciplinary
Yatzil Alejandra Avalos-Quiroz, Olivier Bardagot, Yann Kervella, Cyril Aumaitre, Lydia Cabau, Agnes Rivaton, Olivier Margeat, Christine Videlot-Ackermann, Uyxing Vongsaysy, Jorg Ackermann, Renaud Demadrille
Summary: Four non-fullerene acceptors (NFAs) with extended electron-donating cores and varying solubilizing groups and fluorine atoms were synthesized. The solubilizing groups had minimal impact on optoelectronic properties but influenced organization in the solid state, while the presence of fluorine atoms enhanced optoelectronics properties and increased photo-stability in thin films. Compared to a reference material, the NFAs showed improved absorption across the visible range and higher energy levels. With PM6 as the donating polymer, the NFAs achieved high power conversion efficiencies in solar cells without the need for thermal post-treatment or halogenated additives, making them suitable for industrial applications.
Article
Chemistry, Multidisciplinary
Ary R. Murad, Elham M. A. Dannoun, Shujahadeen B. Aziz, Ahmed Iraqi, Sozan N. Abdullah, Muaffaq M. Nofal, Ranjdar M. Abdullah
Summary: Two alternating copolymers of dithienosilole (DTS) with small optical band gaps were synthesized, incorporating thienyl units as electron-donor moieties and benzothiadiazole dicarboxylic imide (BTDI) as electron-acceptor moieties. The copolymers showed strong thermal stability above 350°C and were amorphous in a solid-state, with comparable HOMO levels and LUMO values.
APPLIED SCIENCES-BASEL
(2021)
Article
Chemistry, Multidisciplinary
Shu I. Takagi, Masahiro Hayakawa, Aiko Fukazawa
Summary: Indenone azines, novel electron-accepting pi-conjugated scaffolds, were synthesized by replacing the exocyclic C=C bond in dibenzopentafulvalene with an azine moiety (C=N-N=C). Stereoselective syntheses of diastereomers with E,E or Z,Z configurations of the two C=N bonds were achieved by structural modulation at the 7,7'-positions. The densely pi-stacked structures of indenone azines, as revealed by X-ray crystallographic analyses, exhibit high coplanarity compared to the twisted frameworks of dibenzopentafulvalene derivatives. Electrochemical measurements and quantum chemical calculations demonstrated that indenone azines have electron-accepting properties similar to isoindigo dyes. Moreover, the 7,7'-dihydroxy-substituted derivatives exhibited enhanced electron-accepting character and significantly red-shifted photoabsorption due to intramolecular hydrogen bonds. These findings suggest that indenone azines are promising electron-accepting building blocks for optoelectronic materials.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Editorial Material
Chemistry, Multidisciplinary
Shu I. Takagi, Masahiro Hayakawa, Aiko Fukazawa
Summary: Indenone azines, a novel class of electron-accepting pi-conjugated scaffolds, were synthesized by replacing the exocyclic C=C bond in dibenzopentafulvalene with an azine moiety (C=N-N=C). Modulating the structure at the 7,7'-positions of indenone azines enabled the stereoselective synthesis of diastereomers with E,E or Z,Z configurations of the two C=N bonds. X-ray crystallography showed that indenone azines have high coplanarity and densely pi-stacked structures. Electrochemical measurements and quantum chemical calculations demonstrated their electron-accepting character comparable to isoindigo dyes. The presence of intramolecular hydrogen bonds in 7,7'-dihydroxy-substituted derivatives enhanced their electron-accepting character and resulted in red-shifted photoabsorption. This study highlights the potential of indenone azines as electron-accepting building blocks for optoelectronic materials.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Energy & Fuels
Li Yang, Xiaoli Zhang, Jinbao Zhang
Summary: This paper discusses the importance of pi-conjugated polymer-functionalized semiconductor surfaces and the use of surface-confined monolayers of these polymers. The nanostructure of the monolayers is influenced by factors such as the type and position of anchor groups, polymer structure, and film-forming techniques. The applications of these monolayers in dye sensitized solar cells and polymer solar cells are summarized. Future research directions for improving the efficiency and assembly states of these monolayers are also discussed.
Article
Chemistry, Physical
Meixue Ke, Tao Ma, Yi Wang, Xiaofang Zeng, Xinrui Miao, Xiaohong Cheng, Wenli Deng
Summary: In this study, the self-assembly behavior of a benzothiadiazole-based fluorophore was investigated in different solvents. The results showed that the self-assemblies exhibited solvent and concentration dependence, with different structures formed at different solvent interfaces. Additionally, the role of chain length in controlling the self-assembly patterns was also observed.
APPLIED SURFACE SCIENCE
(2022)
Article
Chemistry, Physical
Songyao Zhang, Yuantao Liu, Yutuo Zheng, Shibo Chen, Xinrui Miao, Xiaohong Cheng, Wenli Deng
Summary: The self-assembly behaviors of a benzothiadiazole-based liquid crystalline molecule (BT-C14) were investigated using STM. Three different self-assembled patterns were observed at the heptanoic acid/graphite interface, which were not dependent on concentration. The molecular conformations and noncovalent interactions were determined using DFT approaches. The study provides insights for the design of liquid crystalline molecules and analyzing multi-configuration and multi-structure systems in the self-assembly process.
APPLIED SURFACE SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Mark Sigalov, Royi Mazor, Arkady Ellern, Nina Larina, Vladimir Lokshin, Vladimir Khodorkovsky
Summary: Conjugated donor-acceptor molecules with unusual photo- and electro-physical properties have been the focus of research. Through synthesis, X-ray structures, and D-NMR spectra, this study provides a deeper understanding of the conjugation within a series of compounds derived from 1,3-indandione, with varying electron acceptor strength and conjugating bridge length. The findings highlight the influence of intermolecular short contacts on molecular geometries and the unhindered rotation of the phenylamino moiety at room temperature in solution.
Article
Chemistry, Multidisciplinary
Luis Loaeza, Valerie Maraval, Alix Saquet, Gabriel Ramos-Ortiz, Remi Chauvin, Norberto Farfan
Summary: The study focuses on a carbon-rich carbo-benzene derivative with significant photoluminescent properties, synthesized through various methods including reductive aromatization and Sonogashira coupling. Characterization through spectroscopy and voltammetry revealed key properties of the compound, leading to the determination of fluorescence quantum yield. Basic DFT calculations were used to provide insights into electron delocalization within the molecule.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Physical
Kodai Yamanaka, Masahiko Saito, Tomoyuki Koganezawa, Hayato Saito, Hyung Do Kim, Hideo Ohkita, Itaru Osaka
Summary: The crystallinity of pi-conjugated polymer donors and acceptors is crucial for improving the performance of organic photovoltaic cells. In state-of-the-art OPVs based on nonfullerene acceptors, pi-conjugated polymers with low crystallinity are typically used, yet they provide high efficiencies. This study investigates the blending of pi-conjugated polymers PTzBT and PTzBTE with different acceptor materials, revealing that the crystalline order of the blend films is closely correlated with the OPV performance.
ADVANCED ENERGY MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Yao Chen, Jianglin Wu, Shirong Lu, Antonio Facchetti, Tobin J. Marks
Summary: In this study, the structural and electronic properties trends of a series of n-type semiconducting copolymers were evaluated. The reduction of NDI carbonyl groups was found to increase the LUMO energy. Additionally, the thienyl attachment regiochemistry played a significant role in the performance of the copolymers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Hirokazu Miyoshi, Ryosuke Sugiura, Ryohei Kishi, Sarah N. Spisak, Zheng Wei, Atsuya Muranaka, Masanobu Uchiyama, Nagao Kobayashi, Shreyam Chatterjee, Yutaka Ie, Ichiro Hisaki, Marina A. Petrukhina, Tohru Nishinaga, Masayoshi Nakano, Yoshito Tobe
Summary: The dianion and dication of tetramesityl-substituted tetracyclopentatetraphenylene, a circulene consisting of alternating five- and six-membered rings, have been successfully synthesized by reduction and oxidation methods. The theoretical prediction of annulene-within-an-annulene structures has been experimentally proven, with electronic configurations supported by MCD spectra. The distribution of electron charges inside and outside the ions has also been confirmed through experimental analyses.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Physics, Applied
Ersan Y. Muslih, Md. Shahiduzzaman, Md. Akhtaruzzaman, Mohammad Ismail Hossain, LiangLe Wang, Hend I. Alkhammash, Sami S. Alharthi, Masahiro Nakano, Makoto Karakawa, Mohammod Aminuzzaman, Lai-Hock Tey, Kamaruzzaman Sopian, Jean-Michel Nunzi, Tetsuya Taima
Summary: In this study, a nickel oxide (NiO(x)) hole transport layer was fabricated by a simple process without stabilizer or chelating agent. Ethanol and a small amount of nitric acid were used as the solvents. Perovskite solar cells with an optimum thickness of 70 nm showed a high power conversion efficiency and good moisture stability.
APPLIED PHYSICS EXPRESS
(2022)
Article
Physics, Applied
Naoya Yamaguchi, Hiroaki Sano, Hikaru Sawahata, Masahiro Nakano, Tetsuya Taima, Fumiyuki Ishii, Makoto Karakawa
Summary: This study investigated the relationship between the extracted data of organic photovoltaics (OPVs) accompanied by non-fullerene acceptors (NFAs), including power conversion efficiency (PCE), open-circuit voltage (V (OC)), short-circuit current density (J (SC)), and the chemical structures of photovoltaic layer materials. The analysis found a suitable range of V (OC) for achieving high PCE or J (SC) in NFAs. Moreover, the correlation between the performance parameters and chemical structures of small-molecule NFAs was also examined. This approach may provide a new design strategy for high-performance OPVs.
JAPANESE JOURNAL OF APPLIED PHYSICS
(2022)
Article
Materials Science, Multidisciplinary
Keitaro Yamamoto, Sergio Moles Quintero, Seihou Jinnai, Eunjeong Jeong, Kyohei Matsuo, Mitsuharu Suzuki, Hiroko Yamada, Juan Casado, Yutaka Ie
Summary: This study investigates the structure-property relationships in pi-conjugated molecules with quinoidal moieties. The introduction of benzene-annelated units leads to cross-conjugation, which significantly influences the electronic structures. The newly developed quinoidal pentathiophenes demonstrate potential as organic semiconducting materials.
JOURNAL OF MATERIALS CHEMISTRY C
(2022)
Article
Chemistry, Multidisciplinary
Giuseppe M. Paterno, Qiang Chen, Rafael Munoz-Marmol, Michele Guizzardi, Victor Bonal, Ryota Kabe, Alexander J. Barker, Pedro G. Boj, Shreyam Chatterjee, Yutaka Ie, Jose M. Villalvilla, Jose A. Quintana, Francesco Scotognella, Klaus Muellen, Maria A. Diaz-Garcia, Akimitsu Narita, Guglielmo Lanzani
Summary: The synthesis of atomically precise graphene nanostructures provides a new route for the development of environmentally and chemically stable materials with optical gain properties. The introduction of two fluoranthene imide groups to the NG core leads to a more red-shifted and larger Stokes shift emission, enabling efficient NIR lasing with one order of magnitude lower thresholds. This study represents an advance towards the development of cheap and stable NIR lasers in organic semiconductor photonics.
MATERIALS HORIZONS
(2022)
Article
Chemistry, Organic
Shunsuke Tamba, Masashi Nitani, Takuji Seo, Hajime Nitta, Hikaru Tanaka, Kazutake Hagiya, Yoshio Aso, Yutaka Ie
Summary: Incorporating an electron-accepting unit into pi conjugated systems is an important approach to modulate the physical properties of such molecules. In this study, a series of diarylated tetrazolo[1,5-a]pyridine derivatives were synthesized to investigate the potential of tetrazolo[1,5-a]pyridine as an electron-accepting unit. The bithiophene-substituted tetrazolo[1,5-a]pyridine compound exhibited stable transistor characteristics under repeated bias conditions.
Article
Materials Science, Multidisciplinary
Takahiro Fujinuki, Masahiro Nakano, LiangLe Wang, Md. Shahiduzzaman, Makoto Karakawa, Tetsuya Taima
Summary: Organic solar cells (OSCs) with low cost, light weight, and flexibility have gained great interest. A technique of electrode sticker lamination has been developed to fabricate OSCs with good performance and durability by thermocompression. This method solves the weak contact issue between the laminated electrode films and the organic layers.
Article
Chemistry, Multidisciplinary
Soichi Yokoyama, Yutaka Ie
Summary: In this study, a fluorinated dihydropentalene-1,4-dione (FPD) derivative was synthesized as a strong electron-accepting unit for developing D-A-D pi-extended systems. X-ray analysis showed that fluorine atoms facilitated the formation of high planar structures and slipped-stacked packing. Electrochemical measurements revealed that FPD derivatives had lower frontier molecular orbital energy levels compared to DPP-containing derivatives. The D-A-D molecule based on terthiophene and FPD exhibited semiconducting responses. This study demonstrates the potential of FPD as a novel acceptor unit for organic semiconductors.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Seihou Jinnai, Ayumi Oi, Takuji Seo, Taichi Moriyama, Masahiro Terashima, Mitsuharu Suzuki, Ken-ichi Nakayama, Yasuyuki Watanabe, Yutaka Ie
Summary: The complemental absorption behavior of donors and acceptors in organic solar cells (OSCs) leads to broad absorption of solar light, contributing to high-performance OSCs. However, the development of OSCs with narrow absorption ranges, i.e., wavelength-selective OSCs, has been slow due to limited applications. In this study, green-light wavelength-selective OSCs are proposed, which can effectively promote plant growth using the transmitted blue and red light.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Physical
Masahiro Nakano, Tomoki Kobayashi, Masaki Kaneda, Sae Nakagawa, Md Shahiduzzaman, Makoto Karakawa, Tetsuya Taima
Summary: A novel low-temperature sol-gel method to prepare zinc oxide (ZnO) films with reduced photocatalytic activity is reported. Under gentle vacuum conditions, ZnO films exhibit lower photocatalytic activity, leading to higher photodurability of organic optoelectronic devices. The low photocatalytic activity of ZnO films prepared under gentle vacuum could be effective for the development of photodurable non-fullerene organic solar cells with high photovoltaic performance.
SUSTAINABLE ENERGY & FUELS
(2023)
Article
Chemistry, Multidisciplinary
Masahiro Nakano, Hiroki Matsui, Sae Nakagawa, Jiaxun You, Md. Shahiduzzaman, Makoto Karakawa, Tetsuya Taima
Summary: We investigated the effect of self-assembled monolayer (SAM) modification on the resistive switching behavior of ZnO by fabricating electrode-sandwiched devices. SAM-modified ZnO films showed shifted resistive switching voltages compared to bare ZnO due to the surface dipole induced by the SAMs. In particular, methylaminopropyl-substituted SAM-modified ZnO exhibited a lower switching voltage (1.6 V) than bare ZnO (2.9 V). Moreover, SAM modification also improved the on/off ratio (from 10(2) to 10(4)).
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Seihou Jinnai, Naoto Shimohara, Kazunori Ishikawa, Kento Hama, Yohei Iimuro, Takashi Washio, Yasuyuki Watanabe, Yutaka Ie
Summary: A new green-light wavelength-selective nonfullerene acceptor was designed and synthesized to enhance photosynthetic rate and crop yield by fine-tuning the absorbance. Bayesian optimization was applied to optimize the fabrication conditions for improved performance of the green-light wavelength-selective device.
FARADAY DISCUSSIONS
(2023)
Article
Chemistry, Multidisciplinary
Kyohei Matsuo, Rina Okumura, Hironobu Hayashi, Naoki Aratani, Seihou Jinnai, Yutaka Ie, Akinori Saeki, Hiroko Yamada
Summary: An air-stable lambda(3)-phosphinine-containing polycyclic aromatic compound without steric protection was synthesized and its charge transport properties were evaluated, which showed moderate hole mobility. This research is the first experimental demonstration of the organic electronic applications of low-coordinate phosphorus compounds.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Kenji Tsukamoto, Koji Takagi, Seihou Jinnai, Yutaka Ie, Mitsuo Hara, Takanori Fukushima
Summary: In order to control the orientation of the π-conjugated system on the substrate, researchers focused on the molecular shape and synthesized a quasi-3D molecule (Tris-DDB) with a propeller structure. Differential scanning calorimetry (DSC) measurements revealed significant differences in the thermal properties of the three molecules due to intermolecular interactions. Tris-DDB demonstrated the highest thermal stability and, after thermal annealing, exhibited the highest charge carrier mobilities among the three molecules in an OFET device.
MOLECULAR SYSTEMS DESIGN & ENGINEERING
(2022)
Article
Chemistry, Physical
Seihou Jinnai, Kasumi Murayama, Keisuke Nagai, Megumi Mineshita, Kosaku Kato, Azusa Muraoka, Akira Yamakata, Akinori Saeki, Yasuhiro Kobori, Yutaka Ie
Summary: This study introduces a non-fused nonfullerene acceptor (NFA) by utilizing a spiro-substituted 2,7-bis(2-ethylhexyl)fluorene (FT) as a rigid and bulky linker unit. The results show that the introduction of the FT unit leads to the formation of a rigid molecular structure, resulting in improved power conversion efficiency of organic solar cells.
JOURNAL OF MATERIALS CHEMISTRY A
(2022)
