Article
Chemistry, Multidisciplinary
Youzhi Xu, Fabian Steudel, Ming-Yi Leung, Biao Xia, Max von Delius, Vivian Wing-Wah Yam
Summary: Both pillar[n]arenes (P[n]As) and [n]cycloparaphenylenes ([n]CPPs) have been synthesized and integrated into bismacrocycles [n]CPP-P[5]A. The bismacrocycles exhibit higher photoluminescence quantum yield (phi(F)) compared to the corresponding [n]CPPs. Chiral enantiomers (pR)/(pS)-[8]CPP-P[5]A with circularly polarized luminescence (g(lum)approximate to 0.02) were successfully isolated, and the bismacrocycles showed high affinity and specificity towards pyridinium salts and fullerene derivatives. Transient absorption studies revealed photo-induced electron transfer in [10]CPP-P[5]A superset of C-60 complex. The results suggest the potential applications of [n]CPP-P[5]A in CPL-active materials, multiple guest recognition, and supramolecular polymer preparation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Electrochemistry
Veronika Stepanova, Dmitry Shurpik, Ivan Stoikov, Alexey Ivanov, Gennady Evtugyn
Summary: This study describes, for the first time, the cumulative effect of MB concentration, P6, and DNA on MB electropolymerization, using generalized linear models. The results can be applied to optimize the assembly conditions in DNA sensor design.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Fan Zhang, Xu-Sheng Du, Da-Wei Zhang, Yin-Feng Wang, Hai-Yan Lu, Chuan-Feng Chen
Summary: This study reports the synthesis of a nitrogen-doped aromatic belt with a [6]cycloparaphenylene skeleton, showing rigid conjugated structure and deep cavity, as well as strong green fluorescence. The belt-shaped conjugated structure composed of three carbazole subunits has specific optoelectronic properties that will promote wide applications in supramolecular chemistry and materials science.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Nanoscience & Nanotechnology
Tao Sun, Ruonan Chen, Qiuchen Huang, Mengyi Ba, Zhiqiang Cai, Shaoqiang Hu, Xianming Liu, Donatella Nardiello, Maurizio Quinto
Summary: This study reported the fabrication, synthesis, and characterization of a new stationary phase based on an amphiphilic pillar[6]arene for gas chromatographic analyses. The column exhibited medium polarity, high efficiency, and unmatched resolving capabilities. The new stationary phase showed excellent repeatability, indicating great potential for applications in separation science.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Multidisciplinary
Yuzheng Luo, Yang Yang, Yongkang Wang, Zhanpeng Wu, Thomas P. Russell, Shaowei Shi
Summary: The interfacial jamming of nanoparticle surfactants allows for the structuring of liquids and fabrication of all-liquid constructs with multiple responsiveness.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
G. Liu, H. Zhang, X. Xu, Q. Zhou, X. Dai, L. Fan, P. Mao, Y. Liu
Summary: This study presents a photocontrollable light harvesting supramolecular nanoassembly with switchable white light emission, achieved by altering the proportions of energy donor and acceptor center. The designed assembly can reversibly switch between multicolor photoluminescence under different light stimuli, providing potential applications in lighting, display, and anticounterfeiting fields.
MATERIALS TODAY CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xu-Sheng Du, Da-Wei Zhang, Yan Guo, Jing Li, Ying Han, Chuan-Feng Chen
Summary: An efficient method for the synthesis of C(sp3)-bridged [6]cycloparaphenylenes (C[6]CPPs) from fluoren[3]arenes (F[3]As) has been developed, resulting in the synthesis of a new type of macrocyclic arenes. C[6]CPPs exhibit rigid belt-shaped structures and can be selectively methylated to produce fully outer-methyl-substituted derivatives. This research also obtained an unclosed belt with narrow energy gaps and strong fluorescence property, offering potential for the design and synthesis of new aromatic belts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Analytical
R. Shamagsumova, D. N. Shurpik, Y. Kuzin, I. I. Stoikov, A. M. Rogov, G. A. Evtugyn
Summary: The electrochemical behavior of pillar[6]arene (P[6]A) was investigated, and its potential application in electron transfer and supramolecular interactions was discovered.
JOURNAL OF ELECTROANALYTICAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Helena Butkiewicz, Sandra Kosiorek, Volodymyr Sashuk, Magdalena M. Zimnicka, Oksana Danylyuk
Summary: In this study, the solid state supramolecular chemistry of carboxylated pillar[6]arene was explored, and the structure of carboxylated pillar[6]arene was authenticated for the first time. The successful crystallographic authentication was achieved through the host-guest inclusion complexes of carboxylated pillar[6]arene with methyl viologen and pentamidine. The conformation of pillar[6]arene in the inclusion complex was found to be quasi-pentagonal, deviating from the expected hexagonal shape. These results provide insight into the control of the conformation of flexible pillar[6]arene and the design of advanced supramolecular host-guest structures in the solid state.
CRYSTAL GROWTH & DESIGN
(2023)
Article
Nanoscience & Nanotechnology
I. K. Petrushenko, N. Tikhonov, K. B. Petrushenko
Summary: This study systematically investigates the physisorption of H2 molecules by PPA, both pristine and Li+-decorated, in the gas phase. The results show that Li+ decoration significantly enhances the adsorption energy and quantity of adsorbed hydrogen molecules.
PHYSICA E-LOW-DIMENSIONAL SYSTEMS & NANOSTRUCTURES
(2021)
Article
Chemistry, Organic
Shuai Zhao, Tanlong Xue, Di Pei, Qiuyan Song, Zhichao Pei, Jun Nie, Yincheng Chang
Summary: A novel photoinitiator based on the macrocyclic molecule pillar[6]arene has been developed, which exhibits lower migration rate and cytotoxicity compared to commercial photoinitiators. This study represents the first time a macrocyclic molecule has been used as a photoinitiator based on the macrocycle fracture mechanism.
Article
Chemistry, Analytical
Michail Sorvin, Guzeliya Galimzyanova, Vladimir Evtugyn, Alexey Ivanov, Dmitry Shurpik, Ivan Stoikov, Gennady Evtugyn
Summary: A solid-contact potentiometric sensor has been developed using a glassy carbon electrode covered with electropolymerized polyaniline and alternatively layered pillar[6]arene and Cu2+ ions films. The surface layer assembly was confirmed by surface plasmon resonance measurements. The sensor achieved better analytical characteristics for Cu2+ determination by using five layers, with the upper layer consisting of the macrocycle. The sensor allowed for the determination of Cu2+ ions in neutral and weakly acidic media within a linear range of concentrations, from 3.0 mu M to 10.0 mM (limit of detection 3.0 mu M).
Article
Chemistry, Multidisciplinary
Yu Li, Wenjie Li, Weiwei Xu, Jinmei Huang, Zhongyue Sun, Tangbin Liao, Elena G. Kovaleva, Chuanlai Xu, Jing Cheng, Haibing Li
Summary: In this study, glycine-pillar[6]arene (Gly-P6)-functionalized tapered nanochannels were used to selectively transport nucleic acids, overcoming the challenges in extracting high-purity nucleic acids from complex biological samples.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Jiajun Cao, Yitao Wu, Qi Li, Weijie Zhu, Zeju Wang, Yang Liu, Kecheng Jie, Huangtianzhi Zhu, Feihe Huang
Summary: This study provides a rapid and energy-saving method for adsorptive separation of pyrrolidine and tetrahydrofuran using nonporous adaptive crystals of perethyl pillar[6]arene (EtP6). The EtP6 crystals demonstrate superior selectivity towards pyrrolidine and can achieve rapid separation with high purity.
Article
Chemistry, Multidisciplinary
Hui Chong, Cuiyun Nie, Lihong Wang, Sicong Wang, Ying Han, Yang Wang, Chengyin Wang, Chaoguo Yan
Summary: A series of azobenzene-bridged pillar[5]arene-based [3]rotaxanes with different alkyl chain length of guest molecules were constructed and the encapsulation of pillar[5]arenes was verified experimentally. The photo-responsive property of these compounds was demonstrated with the presence of pillar[5]arenes playing a key role in the photo isomerization efficiency.
CHINESE CHEMICAL LETTERS
(2021)
Article
Spectroscopy
Kenya Tanaka, Taishi Nishihara, Akira Takakura, Yasutomo Segawa, Kazunari Matsuda, Yuhei Miyauchi
Summary: In this study, polarized Raman spectroscopy was used to investigate the topological semimetal Co3Sn2S2. The results revealed that the Raman signals at low and high wave numbers are related to phonon modes with different symmetries. The high wave number A1g mode showed an asymmetric peak feature, indicating a Fano resonance with the continuous electronic background. These findings not only serve as fingerprints for verifying the crystal structure of Co3Sn2S2, but also highlight the importance of Raman spectroscopy as an effective tool to study low energy excitations and their interactions in this material.
JOURNAL OF RAMAN SPECTROSCOPY
(2023)
Article
Biochemistry & Molecular Biology
Ayaka Ueda, Yusuke Aihara, Shinya Sato, Keiko Kano, Emi Mishiro-Sato, Hiroyuki Kitano, Ayato Sato, Kazuhiro J. Fujimoto, Takeshi Yanai, Kazuma Amaike, Toshinori Kinoshita, Kenichiro Itami
Summary: This study discovered 2,6-dihalopurines as a new inhibitor of stomatal opening and investigated its mechanism. Biological assays suggested that the pathway related to plasma membrane H+-ATPase phosphorylation may be involved. Through affinity-based pull down assay and molecular dynamics simulation, Leucine-rich repeat extensin proteins (LRXs), LRX3, LRX4, LRX5, and RALF were identified as target protein candidates for 2,6-dihalopurines. The mechanism of stomatal movement related to LRXs-RALF is an unexplored pathway, and further studies may uncover new signaling pathways and regulatory factors in stomatal movement.
ACS CHEMICAL BIOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Ayaka Ueda, Kazuma Amaike, Yoko Shirotani, Hideto Ito, Robin Warstat, Jae-Hoon Choi, Hirokazu Kawagishi, Kenichiro Itami
Summary: Imidazole-4-carboxamide (ICA), a type of fairy chemical (FCs) causing fairy ring phenomena, exhibits plant growth inhibitory activity. FCs have the potential to be a new family of plant hormones as they are endogenous in all tested plant species and regulate plant growth. This study focuses on the synthesis of ICA derivatives and evaluation of their activity in rice. Surprisingly, several compounds show unexpected elongation activity in root and shoot growth.
CANADIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Kou P. Kawahara, Hideto Ito, Kenichiro Itami
Summary: We have developed a sulfur-embedding annulative pi-extension (thia-APEX) reaction to efficiently construct a sulfur-embedding cationic hexagonal aromatic ring called thiopyrylium onto unfunctionalized aromatics in a one-step process. The key of the thia-APEX reaction lies in the utilization of S-imidated ortho-arenoyl arenethiols, enabling easy synthesis of diverse pi-extended thiopyryliums. The synthesized thiopyryliums exhibit various absorption and emission properties across the visible light to NIR region, depending on minor structural variations.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Wataru Matsuoka, Kou P. Kawahara, Hideto Ito, David Sarlah, Kenichiro Itami
Summary: In this study, we successfully achieved a late-stage pi-extension of rubrene using dearomative annulative pi-extension (DAPEX), leading to the generation of rubrene derivatives with an extended aromatic core. These pi-extended rubrenes displayed a marked red shift in absorption and emission spectra, indicating the extension of the rubrene's aromatic pi-system both structurally and electronically. Furthermore, organic field-effect transistor devices using two-side pi-extended rubrene were fabricated, demonstrating the potential utility of these compounds in organic electronics with a comparable carrier mobility to rubrene thin-film transistors.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Nobushige Kai, Hideya Kono, Akiko Yagi, Kenichiro Itami
Summary: A novel structurally constrained nanobelt, methylene bridged [6]cyclo-2,6-naphthylene ([6]MCN), was synthesized via the nickel-mediated intramolecular aryl-aryl coupling of a triflated prism[6]arene. The structural and electronic properties of [6]MCN were characterized using NMR studies and photophysical measurements. In contrast to methylene-bridged [6]cycloparaphenylene, our previously synthesized benzene-based analogue, [6]MCN exhibited low strain energy (77.4 kcalmiddotmol(-1)) and bright fluorescence (Phi = 0.20).
Article
Chemistry, Multidisciplinary
Eiki Tomita, Masahiro Kojima, Yuki Nagashima, Ken Tanaka, Haruki Sugiyama, Yasutomo Segawa, Atsushi Furukawa, Katsumi Maenaka, Satoshi Maeda, Tatsuhiko Yoshino, Shigeki Matsunaga
Summary: The synthesis, characterization, and catalytic performance of an iridium(III) catalyst with an electron-deficient cyclopentadienyl ligand were reported. The catalyst was synthesized by complexation of a precursor of the electron-deficient ligand with an iridium compound, followed by oxidation, desilylation and removal of another ligand. The electron-deficient catalyst enabled C-H amidation reactions assisted by a weakly coordinating directing group.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Hideya Kono, Yuanming Li, Guglielmo Monaco, Riccardo Zanasi, Francesco F. Summa, Lawrence T. Scott, Akiko Yagi, Kenichiro Itami
Summary: Cycloparaphenylenes (CPPs) and carbon nanobelts (CNBs) are cyclic molecular nanocarbons with unique properties derived from rigid, strained, and cyclic p-conjugated systems. The synthesis of various sizes of CPPs and CNBs has allowed for the investigation of their size-dependent properties and use in various applications. The synthesis, size-dependent properties, and paratropic belt currents of methylene-bridged [n]cycloparaphenylenes ([n]MCPP, n = 6, 8, 10) were reported and studied.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Kanna Fujishiro, Yuta Morinaka, Yohei Ono, Tsuyoshi Tanaka, Lawrence T. Scott, Hideto Ito, Kenichiro Itami
Summary: In this study, a lithium(0)-mediated mechanochemical anionic cyclodehydrogenation reaction was developed for the first time. The reaction could be easily performed using a conventional and easy-to-handle lithium(0) wire at room temperature, even under air, and achieved high yields in a short time. The study also comprehensively investigated the applicability and practicality of the protocol, as well as limitations, through computational studies and nuclear magnetic resonance analysis. Furthermore, novel nanographenes, including quinterrylene, were successfully synthesized using this method.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Takaku Yoshihara, Hiroki Shudo, Akiko Yagi, Kenichiro Itami
Summary: Peripheral structural modifications of arenes have a significant impact on their optoelectronic properties, molecular assembly, and stability. Annulation with an adamantane scaffold is a simple yet powerful modification strategy that leads to unique effects, such as high solubility and enhanced conjugation. The oxidation of adamantane-annulated perylenes produces cationic species with extended emission in the near-infrared region, potentially contributing to the development of groundbreaking pi-materials and novel nanocarbon materials.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Multidisciplinary Sciences
Yusuke Aihara, Bumpei Maeda, Kanna Goto, Koji Takahashi, Mika Nomoto, Shigeo Toh, Wenxiu Ye, Yosuke Toda, Mami Uchida, Eri Asai, Yasuomi Tada, Kenichiro Itami, Ayato Sato, Kei Murakami, Toshinori Kinoshita
Summary: The authors identify BITC as a stomatal opening inhibitor that suppresses PM H+-ATPase phosphorylation. They develop BITC derivatives with higher inhibitory activity that increase drought tolerance in plants.
NATURE COMMUNICATIONS
(2023)
Article
Plant Sciences
Yuki Nakashima, Yuka Kobayashi, Mizuki Murao, Rika Kato, Hitoshi Endo, Asuka Higo, Rie Iwasaki, Mikiko Kojima, Yumiko Takebayashi, Ayato Sato, Mika Nomoto, Hitoshi Sakakibara, Yasuomi Tada, Kenichiro Itami, Seisuke Kimura, Shinya Hagihara, Keiko U. U. Torii, Naoyuki Uchida
Summary: A compound called PLU has been discovered to induce the formation of pluripotent callus in plants without the need for external hormone application. The PLU-induced callus expresses marker genes associated with pluripotency acquisition. This study provides a new approach to manipulate and investigate the induction of plant pluripotency.
FRONTIERS IN PLANT SCIENCE
(2023)
Article
Chemistry, Organic
Jaehyun Jung, Takumi Kinoshita, Yuta Makihara, Yota Sakakibara, Kazuma Amaike, Kei Murakami, Kenichiro Itami
Summary: In this study, a decarboxylative aminomethylation of aryl bromides with N-protected glycine under nickel/photoredox-catalyzed conditions was reported. The resulting products can be easily deprotected under acidic conditions to give primary benzylamines.
Review
Chemistry, Organic
Hideto Ito, Kou P. Kawahara, Kenichiro Itami
Summary: Heteroatom-embedded polycyclic aromatic compounds (hetero-PACs) are important in various research fields, and efficient preparation is crucial. This review describes the reactions transforming unfunctionalized aromatic compounds into hetero-PACs using appropriate heteroatom-containing aromatic compounds.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Kou P. Kawahara, Hideto Ito, Kenichiro Itami
Summary: This paper describes the synthesis of pi-extended thianthrene derivatives from unfunctionalized aromatics using thia-APEX reactions. The reaction involves the fusion of new benzodithiine arms to the aromatic substrates in one step, resulting in the formation of pi-extended thianthrenes with yields ranging from 21% to 87%. The reaction requires equimolar amounts of the aromatic substrates and S-diimidated 1,2-arenedithiols, along with a catalytic amount of TfOH, and the synthesized pi-extended thianthrenes were characterized for their solid state packing structures and photophysical properties.
ORGANIC CHEMISTRY FRONTIERS
(2023)
