Article
Chemistry, Applied
Pavletta Shestakova, Margarita Popova, Agnes Szegedi, Hristina Lazarova, Thi Kim Nga Luong, Ivalina Trendafilova, Judith Mihaly, Tatjana N. Parac-Vogt
Summary: The study introduces a novel POM-functionalized hybrid catalyst immobilized on mesoporous silica, with in situ generation of active Bronsted acid sites and Lewis acidity from the metal center during synthesis. These catalysts exhibit higher catalytic activity, recyclability, and leaching resistance compared to common POM-based catalysts.
MICROPOROUS AND MESOPOROUS MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
Supphathee Chaowamalee, Ning Yan, Chawalit Ngamcharussrivichai
Summary: This study focused on the synthesis and characterization of propylsulfonic acid-functionalized nanocomposites based on natural rubber and hexagonal mesoporous silica (NRHMS-SO3H) as heterogeneous acid catalysts. The catalytic performance of these nanocomposites was evaluated in the esterification of levulinic acid with alcohols. Compared to traditional hexagonal mesoporous silica, the NRHMS-SO3H nanocomposites exhibited higher catalytic activity due to the synergistic effect between the strongly acidic-functional group and surface hydrophobicity. Tuning the hydrophobicity and acidity on a nanocomposite surface proved to be an effective strategy for energy reduction in catalysis.
Article
Chemistry, Applied
Edgar Tututi-Rios, Horacio Gonzalez, Denis A. Cabrera-Munguia, Aida Gutierrez-Alejandre, Jose L. Rico
Summary: Through the sol-gel method, Sn-SBA-15 catalysts modified with -PrSO3H groups were synthesized, which significantly improved the acid properties of the catalysts and increased the conversion rate of the esterification reaction between oleic acid and methanol.
Article
Green & Sustainable Science & Technology
M. Srida, S. -Y. Chen, S. M. Smith, C. Ngamcharussrivichai, S. Boonyuen, H. Tateno, T. Mochizuki, A. Luengnaruemitchai
Summary: This study prepared bifunctional solid acid catalysts composed of aluminum (Al) as Lewis acid sites and sulfonic acid (SA) as Bronsted acid sites by direct synthesis. These catalysts were evaluated for the conversion of glucose to 5-hydroxymethylfurfural (HMF) and the 5Al-15SA-S15 catalyst achieved 95% conversion of glucose and a 51% yield of HMF with good stability and reusability. This study provides important insights into the properties and applications of solid acid catalysts.
MATERIALS TODAY SUSTAINABILITY
(2023)
Article
Chemistry, Multidisciplinary
Sabina Siles-Quesada, Christopher M. A. Parlett, Alexander C. Lamb, Jinesh C. Manayil, Yang Liu, Jim Mensah, Hamidreza Arandiyan, Karen Wilson, Adam F. Lee
Summary: Researchers successfully synthesized an ordered macroporous KIT-6 material with 370nm macropores, a face-centered cubic Ia3d structure, and 5nm mesopore channels. After functionalization, this material allows rapid diffusion and esterification of fatty acids. Compared with traditional mesoporous PrSO3H/KIT-6, the esterification rate of fatty acids increased by 5 times, and it also showed a 33% enhancement compared with ordered macroporous PrSO3H/SBA-15.
MATERIALS TODAY CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
N. Hongrutai, S. Watmanee, S. Wannakao, P. Praserthdam, J. Panpranot
Summary: In this study, the surface silanol structures, acid properties, and tungsten dispersion of sol-gel-derived 7W/SiO2-xAl2O3 catalyst were investigated using various analytical techniques. The addition of 1 wt% Al2O3 was found to effectively preserve the Si(OH)Al structure, leading to the best catalytic performance in propene self-metathesis reaction.
MATERIALS TODAY CHEMISTRY
(2021)
Article
Materials Science, Multidisciplinary
Desinta Dwi Ristiana, Suyanta Suyanta, Nuryono Nuryono
Summary: Ethyl levulinate (EL) is an important additive in biodiesel and industrial applications. The most common method for its production involves esterification of biomass-derived levulinic acid (LA) with ethanol (EtOH) using corrosive mineral acid catalysts. To improve the process, researchers have focused on developing highly active solid acid catalysts. In this study, the catalytic activity of sulfonic acid-functionalized silica (SiO2-SO3H) with varying hydrophobicity was investigated. It was found that longer alkyl chains decreased acidity and catalytic activity, while increasing particle size and hydrophobicity. Silica modified with the methyl group (SiO2-SO3H/Me) showed the highest acidity and catalytic performance.
MATERIALS TODAY COMMUNICATIONS
(2022)
Article
Chemistry, Inorganic & Nuclear
Tao Li, Zhichao Tao, Ling Zhang, Yong Yang
Summary: A water-based solgel process was developed for the synthesis of acidity-enhanced amorphous silica-alumina (ASA), which effectively increased acid sites density and reduced cost by using aluminum nitrate nonahydrate. The resulting material exhibited uniform mesopore distribution, large surface area, and high Bronsted-site density, leading to good performance in n-hexadecane hydroisomerization.
JOURNAL OF SOLID STATE CHEMISTRY
(2021)
Article
Chemistry, Physical
N. A. A. Fatah, A. A. Jalil, M. L. Firmansyah, S. Triwahyono, H. D. Setiabudi, D. -V. N. Vo
Summary: In this study, unique fibrous silica ZSM-5 was successfully synthesized using three different alcohols as co-surfactants. The catalysts showed high catalytic activity in hydrocracking due to the absence of diffusion limitation. Among them, FZSM5C3 exhibited the highest catalytic performance due to its high number of Bronsted acid sites.
INTERNATIONAL JOURNAL OF HYDROGEN ENERGY
(2021)
Article
Engineering, Chemical
Vinayak Hegde, Parimal Pandit, Pranita Rananaware, Varsha P. Brahmkhatri
Summary: Sulfonic acid functionalized mesoporous silica catalysts with different morphology were designed and characterized. The cube-shaped catalyst exhibited better catalytic activity compared to the spherical-shaped catalysts, and it also showed good regenerability.
FRONTIERS OF CHEMICAL SCIENCE AND ENGINEERING
(2022)
Article
Materials Science, Ceramics
Wafa Ksila, Mohamed Kadri Younes, Abdelhamid Ghorbel, Alain Rives
Summary: Our research focused on the preparation of new zirconia-doped telluric acid catalysts using the sol-gel method, and investigated the optimization of various preparation parameters on the catalyst. The results showed that the addition of HNO3 significantly improved the acidity of the catalyst, while doping zirconia with telluric acid enhanced both the acidity and catalytic performance of the catalyst. However, calcination of the catalyst led to a loss in acidity and a decrease in catalytic activity.
JOURNAL OF SOL-GEL SCIENCE AND TECHNOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Hui-Chao Ma, Ya-Nan Sun, Gong-Jun Chen, Yu-Bin Dong
Summary: This study reports a facile approach for the asymmetric intermolecular alpha-benzylation of aldehydes using a multifunctional chiral covalent framework catalyst. The reaction can effectively proceed under natural sunlight irradiation and shows broad generality.
Article
Environmental Sciences
Yuting Wu, Jiwen Liu, Shuhui Liu, Wentao Fan, Chenchen Ding, Zhangshan Gao, Zhihui Tang, Yan Luo, Xizhi Shi, Lei Tan, Suquan Song
Summary: Since the outbreak of COVID-19, the increased use of disinfectants has resulted in a significant rise in the generation of disinfection byproducts such as bromoacetic acid (BAA). BAA has raised concerns due to its negative effects on the urinary system in mammals, but its nephrotoxicity and mechanism in birds remain unclear. Through a study involving chicken exposed to different doses of BAA, it was found that BAA exposure caused kidney swelling, structural disarrangement, renal dysfunction, increased apoptosis, and disrupted gene expression related to mitochondrial biogenesis, OXPHOS complex I, and Nrf2 antioxidant reactions. Moreover, BAA also affected genes related to uric acid metabolism, exacerbating kidney damage.
ENVIRONMENTAL TOXICOLOGY
(2022)
Article
Engineering, Chemical
Qing Shu, Xinyuan Liu, Yanting Huo, Yuhui Tan, Caixia Zhang, Laixi Zou
Summary: A novel solid Bronsted-Lewis acid catalyst La-PW-SiO2/SWCNTs was synthesized by modifying H3PW12O40 with single-walled carbon nanotubes functionalized with sidewall hydroxyl groups (SWCNTs-OH) and La3+ via sol-gel method. The catalyst exhibited excellent catalytic activity and stability in the esterification of oleic acid and methanol, attributed to the strong electron withdrawing effect of La3+ on p bond of SWCNTs.
CHINESE JOURNAL OF CHEMICAL ENGINEERING
(2022)
Article
Chemistry, Organic
Linan Hou, Sheng Zhang, Ji Ma, Haiyu Wang, Tienan Jin, Masahiro Terada, Ming Bao
Summary: An organocatalytic atroposelective strategy for the construction of axially chiral compounds containing benzimidazole and quinoline rings is introduced. The reaction of 2-alkynylbenzimidazoles with ortho-aminophenylketones proceeds smoothly in the presence of chiral phosphoric acid, resulting in axially chiral heterobiaryls with good yields and enantioselectivities. This paper presents the first example of combining benzimidazole and quinoline rings at the 2- and 3-positions, respectively, into axially chiral heterobiaryls using this new strategy.
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)
