Article
Chemistry, Applied
Shixiong Chen, Haiyan Pan, Decheng Wan, Ming Jin
Summary: A series of 1,3,5-triaryl-2-pyrazolines were synthesized as photosensitizers for cationic photo polymerization, with excellent light absorption and emission matching for high-performance LED-induced polymerization. The systems, in combination with onium salts, exhibited high quantum yields and promising applications in LED-induced polymerization.
PROGRESS IN ORGANIC COATINGS
(2021)
Article
Chemistry, Physical
Fatemeh Ebrahimi, Hamid Reza Memarian, Hadi Amiri Rudbari, Olivier Blacque
Summary: A series of 4-hydroxy- or 4-methoxy-substituted 1,3,5-triaryl-2-pyrazolines were synthesized and characterized by various spectroscopic techniques. Under UV light, these compounds undergo a non-oxidative photoreaction, resulting in the formation of aromatized pyrazole rings. Density functional theory calculations support an electron-transfer induced photoreaction mechanism.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2023)
Article
Chemistry, Organic
Shuguang Chen, Langxuan Yang, Yongjia Shang, Jianyou Mao, Patrick J. Walsh
Summary: A novel method for synthesizing 2-azaaryl tetrahydroquinolines is reported by the base-promoted tandem reaction of azaaryl methyl amines and styrene derivatives. Mechanistic probe experiments confirm the mechanism involving deprotonation of the benzylic C-H bond and addition to the styrene vinyl group via the SNAr mechanism. High yields of up to 95% were achieved in over 30 examples, demonstrating the potential applicability of this method.
Article
Chemistry, Organic
Yuhang Xue, Chengjun Wu, Haiwen Li, Cunde Wang
Summary: This study investigates the acetic acid-catalyzed (3 + 2) cyclization reaction to efficiently synthesize 4-dicyanomethyl-1,3,5-triaryl-4,5-dihydropyrazoles. The approach demonstrates high yields and predominantly trans-selective double substituents, achieved through consecutive condensation, ring opening, and double nucleophilic cyclization reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yuan-Hong Tian, Han Qin, Man-Hua Ding, Lin-Li Tang, Fei Zeng
Summary: In this paper, the synthesis of water soluble macrocyclic arenes 1 with anionic carboxylate groups was reported. It was demonstrated that host 1 could form a 1:1 complex with N-methylquinolinium salts in water. The complexation and decomplexation of the complexes between host and guests could be achieved by pH variation, and this process could be visually observed.
Article
Chemistry, Multidisciplinary
Darlene Sammut, Nathalie Bugeja, Konrad Szacilowski, David C. Magri
Summary: Several hybrid molecular logic gates were designed and synthesized, achieving photoinduced electron transfer through different substituents. Computational and experimental results showed differences in the electron transfer dynamics between two of the substituents. These compounds in solution exhibited a polarity-tunable internal charge transfer mechanism and colorful solvatochromatism.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Physical
Nicole Zerafa, Miriam Cini, David C. Magri
Summary: Novel 1,3,5-triaryl-2-pyrazolines were designed, synthesized, and covalently immobilized onto submillimeter TentaGel(R) polystyrene beads. These molecules exhibited good performance in terms of aqueous solubility and covalent attachment, and demonstrated fluorescence properties in different logic systems.
MOLECULAR SYSTEMS DESIGN & ENGINEERING
(2021)
Article
Chemistry, Multidisciplinary
Heekyoung Choi, Soichiro Ogi, Naoki Ando, Shigehiro Yamaguchi
Summary: This study reports kinetically controlled supramolecular polymerization of boron-containing p-conjugated molecules using a seeding method based on dual trapping of a metastable state. The formation of helical supramolecular nanostructures with intense J-type aggregate emission was achieved through cooperative supramolecular polymerization. The presence of a Lewis acid-base complex enhanced the stabilization of the metastable monomeric state, allowing for successful production of homogeneous nanofibers even at high concentrations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Inorganic & Nuclear
Alexander J. Bukvic, Martin Albrecht
Summary: Gold-based homogeneous catalysis is mainly achieved through AuI systems. The limited availability of AuIII catalysts for redox reactions is due to the unfavorable potentials for redox cycles between AuI and AuIII. This study presents gold(III) complexes with pincer-based PYA ligands to address these issues. The complexes act as electron reservoirs through two resonance structures, allowed by the flexible coordination sites of the ligands. The presence of a neutral L-type resonance form, as observed in solution data, prevents reversible AuIII reduction and impedes the removal of a chloride ligand. Additionally, a novel macrocyclic-PYA ligand with secondary metal-ligand interactions is introduced.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yue Zhang, Xinyi Wan, Jianbo Gan, Cunde Wang
Summary: The efficient synthesis of 1,2,5-trisubstituted imidazole derivatives was achieved through a DABCO-promoted formal [3+2]-annulation reaction, yielding the corresponding products with moderate to good yields and excellent regioselectivity.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Yue Zhang, Ziman Cai, Yangyang Chi, Xiangzhe Zeng, Shuanghui Chen, Yan Liu, Guo Tang, Yufen Zhao
Summary: Industrially important triaryl phosphites, traditionally prepared from PCl3, have been successfully synthesized using a diphenyl diselenide-catalyzed one-step process involving white phosphorus and phenols, providing a halogen- and transition metal-free method for their production. Oxidation of triaryl phosphites yields triaryl phosphates and triaryl thiophosphates, while phosphorotrithioates can also be efficiently prepared from aromatic thiols and aliphatic thiols.
Article
Chemistry, Multidisciplinary
Rabia Mehmood, Amina Sadiq, Reem Alsantali, Ehsan Ullah Mughal, Meshari A. Alsharif, Nafeesa Naeem, Asif Javid, Munirah M. Al-Rooqi, Gul-e-Saba Chaudhry, Saleh A. Ahmed
Summary: In this study, a library of 1,3,5-triaryl-2-pyrazolines was designed and synthesized. These compounds were screened for their inhibitory activities against urease and alpha-glucosidase. Some compounds showed potent inhibitory activities, with the size and electron effects of substituents influencing the activities.
Article
Polymer Science
Shixiong Chen, Xiaotian Zhao, Ming Jin, Wanqiu Huang, Guodong Ye, Haiyan Pan, Decheng Wan
Summary: The pyrazoline-based sulfonium salt photoacid generators showed high photosensitivity in the 365-425 nm light-emitting diode region, with efficient photolysis and high phi(+)(H) induced by intramolecular charge transfer. The energy of the S-2 orbital was significantly influenced by the heterocycles and their substituted positions, impacting the absorption spectra and quantum yield of photoacid generation.
JOURNAL OF POLYMER SCIENCE
(2021)
Article
Green & Sustainable Science & Technology
Tengfei Guo, Hannian Gu, Ning Wang
Summary: In this study, diethylenetriaminepentaacetic acid (DTPA) was used to dissolve barium in barium slag and recover barium as submicron BaSO4 products through complexation and decomplexation process.
JOURNAL OF CLEANER PRODUCTION
(2022)
Article
Chemistry, Organic
Shimin Jiang, Sha Du, Ruchun Yang, Fengyan Jin, Zhao-Zhao Zhou, Wan-Fa Tian, Xian-Rong Song, Qiang Xiao
Summary: An efficient and practical method for synthesizing triaryl allenyl sulfones was developed using sodium sulfinates as a sulfonyl source and Bronsted acid as a catalyst. The reaction proceeded via allenyl carbocation intermediate and resulted in moderate to excellent yields of allenyl sulfones.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
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, Medicinal
Aya Ogata, Takashi Yamada, Saori Hattori, Hiroshi Ikenuma, Junichiro Abe, Mari Tada, Masanori Ichise, Masaaki Suzuki, Kengo Ito, Takashi Kato, Kazuma Amaike, Tsuyoshi Hirota, Akiyoshi Kakita, Kenichiro Itami, Yasuyuki Kimura
Summary: Positron emission tomography (PET) is a powerful imaging tool for early detection of Alzheimer's disease (AD) that has been developed to target beta-amyloid and tau protein aggregates. This study focuses on the development of a new PET ligand targeting protein kinase CK2, which is known to be altered in AD brains.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(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)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)