Article
Chemistry, Applied
Alexis Truchon, Aurelien Dupeux, Sandra Olivero, Veronique Michelet
Summary: A gold-catalyzed orthogonal tandem reaction using HFIP as a Lewis acid has been developed to access carbocyclic ketone on naphthalene substrates. The yield of cyclic ketones ranged from 15% to 91% using a variety of acenaphthylene carbaldehydes. The mechanism involved a cyclization process followed by an [Au]-HFIP interaction for the final rearrangement. The gram-scale transformation and post-functionalization bromination were successfully carried out.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Timothee Cadart, Tim Glasel, Ivana Cisarova, Robert Gyepes, David Necas, Marko Hapke, Martin Kotora
Summary: Catalytic cyclotrimerization routes to symmetrical [9]helical indenofluorene were investigated using various transition-metal complexes and thermal conditions. The cyclotrimerizations could be accompanied by dehydro-Diels-Alder reaction, resulting in another type of aromatic compounds. The structures of both the symmetrical [9]helical cyclotrimerization product and the dehydro-Diels-Alder product were confirmed by single-crystal X-ray diffraction analyses. Enantioselective cyclotrimerization limits were also examined, and DFT calculations provided insights into the reaction course and the origin of decreased enantioselectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Yang Sik Yun, Claudia E. Berdugo-Diaz, David W. Flaherty
Summary: Biomass has received considerable attention as an alternative to petrochemicals in the production of valuable chemicals and fuels. This Perspective discusses significant advancements in understanding the reaction networks and mechanisms, reactive intermediates, and active site motifs for selective production of desired compounds through hydrogenolysis over heterogeneous catalysts. Continuing research into hydrogenolysis reactions faces current challenges and provides opportunities for future exploration.
Article
Chemistry, Physical
Hora Alhosseini Almodarresiyeh, Siyamak Shahab, Masoome Sheikhi, Liudmila Filippovich, Ekaterina Tarun, Anatoliyi Pyrko, Maksim Khancheuski, Rakesh Kumar
Summary: In this study, two new Acridine Derivatives were synthesized and DFT calculations were performed to investigate their molecular structure and spectral properties in water. The results showed that the chosen computational method can be used to predict other properties of the synthesized molecules. Additionally, the study demonstrated that the new Acridines have good antioxidant properties and may be used for the development of anticancer drugs.
COMPUTATIONAL AND THEORETICAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Nangagoundan Vinoth, Appaswami Lalitha
Summary: A one-pot three component synthesis of novel spiro[acridine-9,3 '-indoline]-1,2 '(2H,10H)-dione derivatives has been successfully achieved under greener conditions, by condensing isatin, dimedone, and aniline. The notable features of this synthesis include the use of a greener solvent (ethanol:water mixture) and the isolation of products by a simple water washing method. The structures of the synthesized compounds have been thoroughly elucidated through various spectroscopic techniques.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Yan Zhen-Shuo, Kang Yan-Hui, Chen Yang-Ling, Huo Li-Ni
Summary: A highly selective iron ions fluorescent probe based on benz(c)acridine-1,2,3-triazole derivatives was synthesized through multi-step reactions. The compound exhibited good selectivity and sensitivity towards iron ions in a DMSO:mops buffer solution, and was successfully utilized for imaging iron ions in living HeLa cervical cancer cells.
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Cong Lu, Rui Chen, Rui Wang, Dong Jing, Ke Zheng
Summary: A new approach for the efficient construction of sulfur-containing oxindoles by photoinduced alkene difunctionalization via sulfur 1,2-relocation is developed. The method showed high functional group tolerance and broad substrate compatibility, allowing the synthesis of a library of sulfur-containing oxindole derivatives under mild conditions. Mechanistic investigations revealed the key steps involved the formation of an EDA complex and the generation of alkenes through C-S bond cleavage.
Article
Chemistry, Organic
Cong Lu, Rui Chen, Rui Wang, Dong Jing, Ke Zheng
Summary: A new method for the efficient construction of sulfur-containing oxindoles via photoinduced alkene difunctionalization is developed. The method showed high functional group tolerance and broad substrate compatibility.
Article
Biochemistry & Molecular Biology
Lina Ammar, Hung-Yu Lin, Shou-Ping Shih, Tsen-Ni Tsai, Yu-Ting Syu, Mohammad Abdel-Halim, Tsong-Long Hwang, Ashraf H. Abadi
Summary: PDE5 inhibitors have anticancer effects and cGMP elevation plays a role in CRC. We synthesized 31 derivatives of 9-benzylaminoacridine and found 22 of them showed micromolar or sub-micromolar inhibition against PDE5. Compounds 11, 12, and 28 exhibited significant growth inhibition, superior Topo II inhibitory activity, low micromolar PDE5 inhibition, and affected cell cycle progression in HCT-116 CRC cells. These compounds have potential as effective therapeutic agents against cancer.
Article
Chemistry, Multidisciplinary
Kai Wang, Xiaoxue Du, Pengfei Zhang, Zhenjiang Wei, Xian-Ting Cao
Summary: A general and straightforward method utilizing N,N-dimethylaniline as the methylenation source has been reported for the regioselective construction of C-3 heteroaryl-containing imidazo[1,2-a]pyridines via cross-dehydrogenative coupling under transition-metal-free conditions. The reaction proceeds through a radical pathway and affords C(sp(2))-C(sp(3)) functionalized products in good to excellent yields.
Article
Chemistry, Inorganic & Nuclear
Jun Li, Constantin G. Daniliuc, Gerald Kehr, Gerhard Erker
Summary: In this study, the reaction of FmesBH(2)·SMe2 with various 1-alkenes to form 1,2-azaborolidine derivatives was investigated.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Multidisciplinary
Arne Merschel, Timo Glodde, Beate Neumann, Hans-Georg Stammler, Rajendra S. Ghadwal
Summary: This study reports the intramolecular 1,2-Dipp migration of seven mesoionic carbenes under nickel catalysis to generate 1,3-imidazoles. The use of these compounds to access super-iMICs demonstrates their superior stereoelectronic properties. The results reveal unprecedented reaction pathways in NHC chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Amel Abdou-Mohamed, Clara Aupic, Corentin Fournet, Jean-Luc Parrain, Gaelle Chouraqui, Olivier Chuzel
Summary: Four-coordinate organoboron derivatives have interesting properties in chemistry, physics, biology, electronics, and optics. The synthesis of smart functional materials based on chiral organoboron compounds is in high demand, making the exploration of stereoselective synthesis of boron-stereogenic organo-derivatives desirable. However, the stereoselective construction of organoboron compounds stereogenic at boron has been less studied due to configurational stability concerns. Nowadays, configurationally stable compounds have been highlighted, showing the potential for stereoselective building of the four-coordinate boron center and encouraging future endeavors and developments in the field.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Organic
Raji Reddy Chada, Roshan Chandrakant Kajare, Mayur C. Bhandari, Siddique Z. Mohammed, Mahender Khatravath, Kamalkishor Warudikar, Nagender Punna
Summary: An efficient method has been developed for the highly diastereoselective construction of functionalized cyclopenta[d][1,2]oxazines through sequential oxyamination and Pauson-Khand reaction of readily accessible propargylic alcohols. Additionally, the ring closing metathesis of these N-O linked 1,7-enynes yielded vinylated-[1,2]oxazines in good yields. The reduction of the N-O bond in the obtained cyclopenta[d][1,2]oxazine allows access to cyclopentenone-based amino alcohols.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Zi-Qi Li, Wen-Ji He, Hui-Qi Ni, Keary M. Engle
Summary: We report a regioselective, nickel-catalyzed carbosulfenylation reaction that introduces both C(sp(3)) and S(Ar)(or Se(Ar)) groups onto non-conjugated alkenyl carbonyl compounds. This reaction is compatible with alkyl/arylzinc nucleophiles and tailored N-S electrophiles, and is complementary to the previously developed 1,2-carbosulfenylation methodology that only allows C(sp(2)) nucleophiles.
Article
Chemistry, Organic
Takuya Shimajiri, Yuta Kawakami, Soki Kawaguchi, Yuki Hayashi, Kazuto Hada, Takanori Suzuki, Yusuke Ishigaki
Summary: This study reports that the bond length of flexible C-C single bonds surrounded by bulky alkyl groups in novel hexaphenylethane-type hydrocarbons can be affected by weak noncovalent interactions, such as London dispersion. An ultralong and flexible C-C single bond exhibits an obvious bond contraction due to the effect of London dispersion. X-ray analysis and Raman spectroscopy provide direct information about bond length and strength, while density functional theory calculations explain the bond contraction driven by London dispersion. The change in bond length of an extremely elongated flexible C-C bond can be a useful method for quantifying weak interactions that are typically difficult to detect.
Article
Chemistry, Multidisciplinary
Yujing Ma, Kazuma Sugawara, Yusuke Ishigaki, Kewei Sun, Takanori Suzuki, Shigeki Kawai
Summary: We successfully synthesized pyrrolopyrrole-bridged ladder oligomers from 11,11,12,12-tetrabromo-1,4,5,8-tetraaza-9,10-anthraquinodimethane molecules on Ag(111) using bond-resolved scanning tunneling microscopy. The non-dehydrogenative cyclization between pyrazine and ethynylene/cumulene groups has a low-activation barrier, forming dimeric oligomers containing dipyrazinopyrrolopyrrolopyrazine units and providing new insights into strain sensitivity in ladder-oligomer formation.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Takashi Harimoto, Takanori Suzuki, Yusuke Ishigaki
Summary: By introducing ortho-substituents on the 4-methoxyphenyl group, the NIR-absorbing properties can be changed and the HOMO and LUMO levels can be fine-tuned. This study demonstrates that the ortho-substitution strategy is an effective approach for modifying electrochemical and spectroscopic properties.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Ryohei Mizoue, Moeko Kawana, Takashi Takeda, Norihisa Hoshino, Tomoyuki Akutagawa
Summary: Intermolecular interactions in molecular crystals, such as hydrogen bonding, halogen-halogen, and van der Waals interactions, play a crucial role in determining phase transition behaviors and physical properties. The study focused on bis(tetradecylamide)-substituted benzene derivatives, particularly the effects of different substituents on the molecular assembly structure and properties. It was found that H-and CH3-substituted derivatives formed a crystalline phase dominated by hydrogen bonding, while halogen-substituted derivatives formed a metastable glass phase due to the competition between different interactions. The glass-crystal phase transition of halogen-substituted derivatives exhibited changes in refractive index, which could be utilized for phase-change memory.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
Article
Chemistry, Multidisciplinary
Yuta Nishimura, Takashi Harimoto, Takanori Suzuki, Yusuke Ishigaki
Summary: A nitrogen-centered heptalene, azaheptalene, was designed as a representative of a new class of redox-responsive molecules with a large steric strain. The pentabenzo derivative of azaheptalene was efficiently synthesized by a palladium-catalyzed one-pot reaction. Bromination led to mono- and dibrominated derivatives, with the latter exhibiting near-infrared absorption as isolable radical cation species. Optically pure azaheptalenes with P- or M-helicity showed strong chiroptical properties, which could be changed by an electric potential.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Takashi Harimoto, Yuka Sugai, Kazuma Sugawara, Takanori Suzuki, Yusuke Ishigaki
Summary: By synthesizing new octakis(aminophenyl)-substituted pentacenebisquinodimethane (BQD) derivatives and their hybrids with alkoxyphenyl analogues, the study successfully generated and isolated dicationic and tetracationic states with apparent two-electron transfer, minimizing the involvement of open-shell species. This achievement allows for the development of multi-color electrochromic systems with improved reversibility.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Kosuke Ono, Keisuke Sawanaga, Satoru Onodera, Hidetoshi Kawai, Kei Goto
Summary: A novel structural interconversion unit based on intramolecular boroxine formation has been developed. The macrocyclic triboronic acid preferentially undergoes intramolecular boroxine formation, resulting in the formation of tricyclic boroxine. This transformation is accompanied by changes in the polarity, flexibility, and size of the molecule. The entropically stabilized tricyclic boroxine shows high stability with respect to hydrolysis.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Takuya Shimajiri, Henri-Pierre Jacquot de Rouville, Valerie Heitz, Tomoyuki Akutagawa, Takanori Fukushima, Yusuke Ishigaki, Takanori Suzuki
Summary: Studies on TCNQs fused with [1,2,5]chalcogenadiazole rings show that chalcogen bonds (ChBs), through E···C (E = S or Se) contacts, play a decisive role in determining their crystal structures and electron conduction. ChBs also enable molecular recognition and solid-state reactions, such as charge-transfer-type clathrate formation and photoinduced electron transfer. These ChB-based materials have promising potential for the development of novel solid-state functions.
Article
Chemistry, Multidisciplinary
Yusuke Ishigaki, Takuya Tachibana, Kazuma Sugawara, Moto Kikuchi, Takanori Suzuki
Summary: Macrocyclic dications 2(2+), composed of two triarylmethylium units, were designed and synthesized. These dications exhibited mechanochromic emission extending to the red region due to their constrained structures and proper counterion choice. The mechanochromic behavior was induced by crystal-to-amorphous transition, and intermolecular interaction played a key role in changing the emission pattern.
Article
Chemistry, Multidisciplinary
Haruka Abe, Takashi Takeda, Tomoyuki Akutagawa
Summary: The study investigates the hydrogen bonding interactions in host-guest crystals and reveals the influence of different halobenzene derivatives on crystal structure and lattice. Furthermore, it demonstrates that heat treatment and vapor diffusion can induce changes in crystal structure and guest adsorption behavior.
CRYSTAL GROWTH & DESIGN
(2023)
Article
Chemistry, Inorganic & Nuclear
Kiyonori Takahashi, Takashi Takeda, Xin Zheng, Shin-ichiro Noro, Tomoyuki Akutagawa, Takayoshi Nakamura
Summary: The structural changes of a coordination polymer associated with gas adsorption can be correlated with physical properties like magnetism, electrical conductivity, and dielectric properties. In this report, a crystalline sample of a one-dimensional coordination polymer is shown to exhibit selective CO2 adsorption and dielectric switching behavior in a mixed N-2/CO2 gas environment. The CO2 adsorption process accompanies a structural change and is supported by the changes in dielectric permittivity and enthalpy associated with CO2 adsorption.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Ryo Ide, Ayumi Kawasaki, Takashi Takeda, Shun Dekura, Norihisa Hoshino, Wakana Matsuda, Shu Seki, Tomoyuki Akutagawa
Summary: A supramolecular approach was used to control the molecular arrangement of functional organic π-molecules through intermolecular electrostatic hydrogen-bonding interactions. Anionic N,N-bis(ethylphosphonate)-naphthalene diimide (DPNDI(2-)) with proton conducting -PO3H- groups was designed as a n-type semiconductor. Single crystals of (Na+)(2)(DPNDI(2-))•(H2O)2.0 (1) and (NH4(+))(2)(DPNDI(2-)) (2) were formed, exhibiting a Herringbone-type NDI arrangement. Proton conduction was observed in crystal 2 through a 2D electrostatic NH4(+)-PO3H- hydrogen-bonding network, with a conductivity of 1.5 x 10(-4) S cm(-1) at T = 423 K. Thin films of PMMA mixed with crystal 1 or 2 maintained a similar molecular arrangement to the bulk crystal and showed transient conductivities of 6.8 x 10(-4) and 6.9 x10(-4) cm(2) V-1 s(-1) respectively.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
Article
Chemistry, Multidisciplinary
Kazuma Sugawara, Toshikazu Ono, Yoshio Yano, Takanori Suzuki, Yusuke Ishigaki
Summary: Tetraarylated quinodimethanes have various conformations but obtaining all of them is challenging. To overcome this, flexible polyaryl-substituted tetraazaanthraquinodimethanes were designed with reduced steric hindrance. X-ray analysis showed that these molecules could adopt folded, twisted, and intermediate structures in pseudopolymorphs. Due to different electronic configurations, the crystal colors varied from yellow to red, with the crystal containing twisted conformers emitting red to near-infrared light. This represents the first flexible quinodimethanes with tunable photophysical properties and multi-chromic behavior based on multiple conformations.
MATERIALS CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Kewei Sun, Kazuma Sugawara, Andrey Lyalin, Yusuke Ishigaki, Kohei Uosaki, Oscar Custance, Tetsuya Taketsugu, Takanori Suzuki, Shigeki Kawai
Summary: In this study, complex organometallic oligomers were systematically synthesized on Cu(111) through sequential ring opening and bonding of phenanthroline derivatives by multiple Cu atoms. Characterization using scanning tunneling microscopy and density functional theory calculations revealed the role of Cu adatoms in the chiral oligomers. Furthermore, the strength of the bonds against sliding friction was found to be sufficient.
Article
Chemistry, Multidisciplinary
Takashi Harimoto, Tomoki Tadokoro, Soichiro Sugiyama, Takanori Suzuki, Yusuke Ishigaki
Summary: The concept of a domino reaction has been successfully applied to redox chemistry in this study, where a change in molecular conformation was used to trigger a domino redox reaction. This provides a new approach and method for developing novel redox reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(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)
