Article
Chemistry, Organic
Sandya Tambi Dorai, Kyatagani Lakshmikanth, Priya Tiwari, Surbhi Mahender Saini, Sandeep Chandrashekharappa
Summary: A one-pot three-component method for the synthesis of 3-substituted 2-trifluoromethyl-2,3-dihydroimidazo[1,2-a]pyridin-3-yl analogues from 2-aminopyridine, substituted phenacyl bromides, and trifluoroacetaldehyde methyl hemiacetal (TFAMH) under solvent-free and the catalyst-free condition is described. The method shows good to excellent yield and employs an additive-free approach with safe, stable, and readily available starting materials, offering a wide substrate scope.
Article
Crystallography
Franz A. Mautner, Florian Bierbaumer, Roland C. Fischer, Ramon Vicente, Annia Tubau, Arnau Ferran, Salah S. Massoud
Summary: The four new Pr(III) mononuclear complexes have been synthesized and structurally characterized, showing different coordination numbers and structures. The ancillary chelating bipyridyl ligands greatly enhance the luminescence emission of the complexes through efficient energy transfer to the central Pr3+ ion.
Article
Biochemistry & Molecular Biology
Franz A. Mautner, Florian Bierbaumer, Ramon Vicente, Saskia Speed, Annia Tubau, Merce Font-Bardia, Roland C. Fischer, Salah S. Massoud
Summary: A series of mononuclear Ho3+ complexes derived from beta-diketonate anions have been synthesized and characterized. These complexes exhibit a coordination number of 8 for the central Ho3+ ions. The pyridyl adducts show strong luminescence emissions in the visible and near-infrared regions. The magnetic properties of the complexes reveal no field-induced single-molecule magnet behavior.
Article
Chemistry, Organic
Zhongxue Fang, Qihao Jin, Xinyu Wang, Yongquan Ning
Summary: A transition-metal-free [2 + 1 + 3] cycloaddition reaction of trifluoroacetaldehyde N-sulfonylhydrazone and hexahydro-1,3,5-triazine was described, providing a general synthesis of diverse trifluoromethylated 2,3,4,5-tetrahydro-1,2,4-triazines in good yields (81-97%) with a broad substrate scope, including aryl, benzyl, and alkyl hexahydro-1,3,5-triazine.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shan-Shan Liu, Qi-Ming Guo, Bin Liu, Teng-Hui Jin, Zi-Hao Zhang, Shijing Lin, Yin-Shan Meng
Summary: Two mononuclear complexes, [(tfnb)(3)Ln(phen)] (Ln = Tb or Dy, tfnb = 4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedione, phen = 1,10-phenanthroline), were structurally determined using single crystal X-ray diffraction. The crystallographic data showed that the two complexes have isostructural trigonal dodecahedral geometries. The dysprosium complex exhibited slow relaxation of magnetization without a dc field, with an effective barrier U-eff of 193 K obtained by considering QTM, Raman, and Orbach processes for energy barrier fitting. The calculated magnetic easy axis using an electrostatic model aligned with the direction of the two tfnb(-) ligands in the trans position.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ramon Vicente, Annia Tubau, Saskia Speed, Franz A. Mautner, Florian Bierbaumer, Roland C. Fischer, Salah S. Massoud
Summary: In this study, five new eight-coordinated Nd(iii) mononuclear complexes were synthesized and characterized. Three of these complexes exhibit single-molecule magnet behavior with significant anisotropy energy barriers. The use of ancillary chelating bipyridine ligands greatly enhances solid state luminescence emission in the visible and NIR regions.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Analytical
Mohammed A. Al-Anber, Neda'a Al-Adaileh, Idrees F. Al-Momani, Zaid Al-Anber
Summary: The thenoyl-trifluoro-acetone has been successfully encapsulated into silica gel matrix to form composite SG-TTA, which shows high efficiency in removing and capturing uranium (VI) ion species. Experimental data indicates that SG-TTA composite material can efficiently remove uranium ions from water under specific conditions.
JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY
(2021)
Article
Chemistry, Physical
D. Jaya Reshmi, H. Marshan Robert, D. Aruldhas, I. Hubert Joe, S. Balachandran
Summary: The molecule 4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedione was investigated using experimental and theoretical spectroscopic methodologies. Various properties such as vibrational frequencies, charge delocalization, UV-Visible spectrum, and solvents effects were analyzed. The study also looked into orbital contributions, HOMO and LUMO energies, as well as softness and electrophilicity indices of the molecule. Electron density weak interactions and chemical reactivity sites were identified, and nonlinear optical properties were examined using different techniques.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Physical
Suman Meena, Rajni Grover, Prerna Bansal
Summary: This study experimentally investigated the stability of Cd(II) complexes with amino acids and 4,4,4-trifluoro-1-(2-naphthyl)-1,3- butanedione at a dropping mercury electrode. The results showed that the neutral [Cd(X)(Y)] complexes were more stable than the charged [Cd(X)2(Y)]-1 and [Cd(X)(Y)2]-1 complexes.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Physical
Manikumar Athan, J. Josephine Novina, Nagarajan Loganathan
Summary: By conducting X-ray diffraction and DFT analysis, this study reveals that a simple room temperature stirring reaction of MnCl2 center dot 4H(2)O and 4,4,4-trifluoro-1-phenyl-1,3-butanedione (TFPBDH) produces yellow crystals of monomeric, square-planar Mn(TFPBD)2. ESI-MS analysis confirms the solution stability of Mn(TFPBD)2, which is further supported by FT-IR and UV-Vis analysis. Quantum theory analysis and molecular docking demonstrate the stable supramolecular architecture and the excellent binding affinity of Mn(TFPBD)2 towards penicillin-binding protein 2 and staphylococcal aureus FtsZ.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Inorganic & Nuclear
Franz A. Mautner, Florian Bierbaumer, Ramon Vicente, Saskia Speed, Annia Tubau, Roland C. Fischer, Salah S. Massoud
Summary: This article reports a novel series of polypyridyl adducts and analyzes their optical and magnetic properties. The experimental results show that these compounds have high quantum yields and no saturation at high magnetic fields.
Article
Chemistry, Physical
M. K. Hema, C. S. Karthik, Mahesha, K. J. Pampa, P. Mallu, N. K. Lokanath
Summary: In this study, two beta-diketone metal complexes were synthesized and characterized using various techniques, showing inhibitory effects on MRSA growth. The copper complex exhibited a better inhibition effect on MRSA compared to the nickel complex.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Inorganic & Nuclear
R. R. Macedo, P. I. S. Maia, V. M. Deflon, G. F. de S. Miguel, A. E. H. Machado, G. Von Poelhsitz
Summary: In this study, a new complex cis-[Ru(dppm)(2)(bta)]PF6 was prepared from the precursor cis-[RuCl2(dppm)(2)] under mild conditions. The complex was characterized by elemental analysis, spectroscopy (FTIR, H-1, P-31{H-1}, and F-19{H-1} NMR), and single-crystal X-ray diffraction, which confirmed its high purity and a distorted tetrahedral geometry for the ruthenium center.
JOURNAL OF STRUCTURAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Ilya Taydakov, Yury A. Belousov, Mikhail T. Metlin, Victoria E. Gontcharenko
Summary: A binuclear gadolinium (III) complex was synthesized through the reaction of GdCl3·6H2O, 4,4,4-trifluoro-1-(1-methyl-1H-pyrazol-4-yl)butane-1,3-dione and NaOH in methanol solution. The complex exhibited promising luminescent properties, making it suitable for the preparation of highly luminescent Eu3+ and Sm3+ complexes.
Article
Chemistry, Organic
Futa Ogawa, Yukiko Karuo, Ryuji Yamazawa, Kanae Miyanaga, Kazushige Hori, Keita Tani, Kengo Yamada, Yuki Saito, Kazumasa Funabik, Atsushi Tarui, Kazuyuki Sato, Kiyoshi Ito, Kentaro Kawai, Masaaki Omote
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Ryunosuke Kani, Toshiyasu Inuzuka, Yasuhiro Kubota, Kazumasa Funabiki
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Miki Matsuda, Yasuhiro Kubota, Kazumasa Funabiki, Daisuke Uemura, Toshiyasu Inuzuka
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Organic
Kazumasa Funabiki, Kengo Yamada, Hisaki Matsueda, Yuta Arisawa, Tomohiro Agou, Yasuhiro Kubota, Toshiyasu Inuzuka, Hiroaki Wasada
Summary: The introduction of a perfluorophenyloxy group at the 5-position of 3,3-dibutyl-2-methyl-3H-indole efficiently enhances aggregation-induced emission in both the crystalline solid-state and in highly concentrated ethanolic solutions of the resultant analog. This phenomenon is attributed to aggregate formation due to perfluorophenyl-perfluorophenyl stacking between the 3H-indole units.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yasuhiro Kubota, Kenta Koide, Yuka Mizuno, Masato Nakazawa, Toshiyasu Inuzuka, Kazumasa Funabiki, Hiroyasu Sato, Masaki Matsui
Summary: Unsymmetrical 1,4-dihydropyrrolo[3,2-b]pyrroles were synthesised and their absorption and fluorescence properties were investigated. Different substituents led to significant differences in the emission wavelength, while the fluorescence properties were also affected by the solvent environment.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Ryunosuke Kani, Toshiyasu Inuzuka, Yasuhiro Kubota, Kazumasa Funabiki
Summary: We have developed a functional-group-tolerant one-pot method for synthesizing various 3-substituted 1-trifluoromethylpropargyl alcohols. This method involves three successive reactions and can be applied to different fluorine-containing esters and terminal alkynes. The obtained products can be further transformed into important compounds for the treatment of pain and inflammation associated with osteoarthritis in dogs.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yuta Arisawa, Yasuhiro Kubota, Toshiyasu Inuzuka, Kazumasa Funabiki
Summary: In this study, near-infrared-absorbing anionic heptamethine cyanine (HMC) dyes were synthesized and their photostability and halochromic properties were investigated. By substituting the methyl groups of the anionic HMC dye with phenyl or perfluorophenyl groups, the maximum absorption wavelengths of the dye solutions were red-shifted, and the photostability of the dye in solution under white LED irradiation was improved. The anionic HMC dye with methyl groups exhibited halochromic properties, causing the solution color to change from green to yellow in the presence of acids. This study presents the first reported anionic HMC dye with halochromic properties. Additionally, a stimuli-responsive filter paper adsorbed with anionic HMC dyes was developed, showing color changes from green to yellow upon exposure to HCl gas and from yellow to green upon subsequent exposure to NH3 gas.
Article
Chemistry, Organic
Kazumasa Funabiki, Kengo Yamada, Yuta Arisawa, Arina Watanabe, Tomohiro Agou, Yasuhiro Kubota, Toshiyasu Inuzuka, Yohei Miwa, Taro Udagawa, Shoichi Kutsumizu
Summary: A series of perfluoronaphthalene-based donor-acceptor-donor fluorescent dyes were successfully synthesized using a one-step route. The perfluoronaphthalene moiety served as a good electron-accepting aromatic ring with excellent intramolecular charge transfer properties. Replacing the naphthalene ring with perfluoronaphthalene stabilized the energy levels and reduced the energy band gap, leading to a change in the emission color. Among the synthesized dyes, those with diphenylamino groups showed the highest fluorescence quantum yields in solution and film, while the dye with carbazoyl group exhibited the highest fluorescence quantum yield in the crystalline state.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Hiroki Masuoka, Yasuhiro Kubota, Toshiyasu Inuzuka, Kazumasa Funabiki
Summary: A new anionic heptamethine cyanine (HMC) dye with two trifluoromethyl groups has been synthesized, which selectively absorbs near-infrared light. Compared with previously studied anionic HMC dyes with substituents such as methyl, phenyl, and pentafluorophenyl groups, the trifluoromethylated dye exhibits a red-shifted maximum absorption wavelength (e.g. 948 nm in CH2Cl2) and enhanced photostability. Furthermore, HMC dyes with broad absorption in the near-infrared region are synthesized by combining a trifluoromethylated anionic HMC dye with a cationic HMC dye as a counterion.
Article
Chemistry, Multidisciplinary
Yuki Uehashi, Seiichiro Izawa, Yuya Yamada, Yohei Miwa, Toshiyasu Inuzuka, Yasuhiro Kubota, Masahiro Hiramoto, Kazumasa Funabiki
Summary: We studied the photodegradation of non-fluorinated benzoindolenine-based SQ dyes with low photostability in solution and proposed a hypothesis to improve their photostability. The replacement of hydrogen atoms with fluorine atoms or methylation of the oxygen anions resulted in improved photostability. Furthermore, the synthesized SQ dyes with bulky fluorine-containing anions provided a higher Voc for organic photovoltaics.
Article
Chemistry, Multidisciplinary
Ryunosuke Kani, Yohei Miwa, Yasuhiro Kubota, Toshiyasu Inuzuka, Shoichi Kutsumizu, Kazumasa Funabiki
Summary: Our optically CO2-responsive polydimethylsiloxane (PDMS) elastomer undergoes rapid and reversible color changes in the presence of CO2 gas. Unlike conventional optically CO2-responsive polymeric materials, it functions in totally dry gaseous conditions.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Mikiko Shibayama, Yuki Uehashi, Shouhei Ajioka, Yasuhiro Kubota, Toshiyasu Inuzuka, Kazumasa Funabiki
Summary: Here, we introduce an organic-inorganic hybrid material consisting of an indolenine-based heptamethine cyanine dye adsorbed on silica gel. This material exhibits vapochromism towards amines or chlorinated solvents, resulting in a color change.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ryunosuke Kani, Yasuhiro Kubota, Toshiyasu Inuzuka, Kazumasa Funabiki
Summary: This study proposes a powerful method of introducing multiple fluorine atoms into the aromatic rings of trimethine cyanine dyes to significantly increase sensitivity to amines. The highly sensitive ratiometric fluorescence properties, previously only usable in intramolecular addition reactions, can now be utilized in reactions with intermolecular amines or other nucleophiles.
Article
Chemistry, Organic
Yasuhiro Kubota, Masato Nakazawa, Junheon Lee, Ryoma Naoi, Motoki Tachikawa, Toshiyasu Inuzuka, Kazumasa Funabiki, Masaki Matsui, Taekyeong Kim
Summary: The study focused on the synthesis of 1,3- and 1,2-Bis(pyrrol-2-yl)squaraines and discussed their maximum absorption wavelength characteristics. It was found that the thiophene-fused 1,3-squaraine exhibited near-infrared absorption and fluorescence. Additionally, protonation could modulate the absorption wavelength, indicating that mono-cationization is an effective strategy for achieving a red-shift in the wavelength.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Kazumasa Funabiki, Toshiya Gotoh, Ryunosuke Kani, Toshiyasu Inuzuka, Yasuhiro Kubota
Summary: This study developed a highly selective method for synthesizing erythritols bearing a trifluoromethyl group, involving the in situ generation of unstable trifluoroacetaldehyde through organocatalysis and achieving high yield, diastereoselectivity, and enantioselectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)