Article
Chemistry, Multidisciplinary
Xiaoqian Wang, Jiecheng Ji, Ming Rao, Wanhua Wu, Cheng Yang
Summary: In this study, sulfoxide- and sulfone-bridged beta-cyclodextrin dimers were synthesized for the enantiodifferentiating [4+4] photocyclodimerization of 2-anthracenecarboxylic acid. The product distribution and enantioselectivity were found to be influenced by the chemical structure of the bridged CDs. The presence of CsCl enhanced the relative yields and ee values of the slipped cyclodimers, while the reaction selectivity was affected by the pH variation of the aqueous buffer solution, indicating a multidimensional control over supramolecular photochirogenesis.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Organic
Pengyue Jin, Yanqin Rong, Wenting Liang, Xiaotong Liang, Runhua Lu, Wuanhua Wu, Min Gou, Yueqin Tang, Cheng Yang, Yoshihisa Inoue
Summary: Catalytic enantiodifferentiating photoisomerization of cyclooctene can be achieved by sensitization with regioisomeric beta-cyclodextrins under specific solvent conditions, resulting in high enantioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemical Research Methods
Xueqin Wei, Jiecheng Ji, Yongxin Nie, Liangjian Tang, Ming Rao, Xiaoqian Wang, Wanhua Wu, Dan Su, Zhihui Zhong, Cheng Yang
Summary: Photochemical methods are increasingly used in organic synthesis, with supramolecular strategies playing a promising role in controlling stereochemistry in chiral photoreactions.
Cyclodextrin derivatives are widely applied chiral hosts for mediating photoreactions, leading to enhanced enantioselectivity.
The protocol for chiral photoreactions includes preparation of derivatives, host-guest inclusion behavior studies, operation of the photoreaction, and chiral HPLC analyses, resulting in excellent regio- and enantioselectivities.
Review
Chemistry, Multidisciplinary
Matthew J. Genzink, Jesse B. Kidd, Wesley B. Swords, Tehshik P. Yoon
Summary: Asymmetric photocatalysis is a major research topic in contemporary synthetic organic chemistry. However, the discovery of general strategies for highly enantioselective photochemical reactions has been a recent development, leading to a somewhat limited variety of stereocontrolled photoreactions. This review summarizes the chiral catalyst structures that have been studied for solution-phase asymmetric photochemistry, providing insight into the logic required for highly effective stereocontrolled photocatalysis.
Article
Chemistry, Multidisciplinary
Philipp Niermeier, Kristina A. M. Maibom, Jan-Hendrik Lamm, Beate Neumann, Hans-Georg Stammler, Norbert W. Mitzel
Summary: In this study, 1,8-dialkynylanthracene photo-dimers were prepared in head-to-head configuration using 2-hydroxypropyl-protecting groups and demonstrated their applicability as a building block for a tetradentate boron Lewis acid. The formation of adducts with various nitrogen bases showed the potential of the compound as a host for Lewis-base substrates, with impressive networks formed between the tetraboron host and the substrate molecules in the case of adduct formation with hydrazine.
Article
Chemistry, Organic
Nao Shimizu, Hajime Shigemitsu, Toshiyuki Kida, Thorsten Bach, Tadashi Mori
Summary: A range of asymmetric photochemical transformations using visible light have recently become considerably attractive. Chiral Lewis acid association to enones for [2 + 2] and ortho photocycloadditions and oxadi-pi-methane rearrangements have shown to be very promising in achieving effective enantiodifferentiation. In this study, we investigated the regio- and enantiodifferentiation of [2 + 2] photocycloaddition reactions of naphthoquinone derivatives mediated by chiral oxazaborolidines. We found that the excited-state decomplexation is a key factor in achieving high regio- and enantioselectivities in the photocycloaddition reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kuppusamy Kanagaraj, Jiecheng Ji, Ming Rao, Chunying Fan, Chao Xiao, Dayang Zhou, Wanhua Wu, Narayanan Selvapalam, Yang Yu, Cheng Yang
Summary: A series of modified beta-cyclodextrins with mono/bis-quinoline tethers were synthesized and found to significantly enhance the enantiodifferentiating photocyclodimerization reactions, with the stereochemical outcomes being reversely affected by changing the solution pH.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Engineering, Chemical
Qi Zhang, Siru Ren, Song Xue, Ang Li, Siyao Liu, Xiaodong Sun
Summary: The study evaluated six novel ionic liquids as chiral selectors in capillary electrophoresis, showing better enantioseparation performance compared to traditional chiral selectors.
SEPARATION AND PURIFICATION TECHNOLOGY
(2021)
Review
Chemistry, Multidisciplinary
Jiecheng Ji, Xueqin Wei, Wanhua Wu, Cheng Yang
Summary: Recent research has shown that the supramolecular strategy can control the stereochemical outcomes of asymmetric photoreactions by using strong and long-lasting noncovalent interactions at both ground and excited states. The chiral hosts/assemblies provide a chiral environment for transferring chirality to the photosubstrates, and the supramolecular complexation can manipulate the orientation and conformation of the photosubstrates to ensure the desired stereoselective photochemical conversion.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Engineering, Chemical
Todd A. Hopkins, Liam VandenElzen, Brian P. Nelson, Vishnu Vaid, Jayme Brickley, Paola Ariza, Grace Whitacre, Inaya Patel, Olivia Gooch, Mandy Bechman, Charlotte Jordan
Summary: Deep eutectic solvents (DES) are mixtures with a much lower melting point than any of the components. DES have potential as solvents in various applications due to their controllable properties. Developing high throughput methods for DES discovery is crucial because of the large number of potential components.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Md Nurul Huda, Isaac G. Deaguro, Edgar A. Borrego, Raj Kumar, Tamanna Islam, Humayra Afrin, Armando Varela-Ramirez, Renato J. Aguilera, Eden E. L. Tanner, Md Nurunnabi
Summary: This study developed a topical formulation composed of Navitoclax and an ionic liquid of choline octanoate. The results showed that COA-mediated topical delivery of Navitoclax was more effective in treating early-stage melanoma than oral administration.
JOURNAL OF CONTROLLED RELEASE
(2022)
Article
Engineering, Chemical
Qi Zhang, Siru Ren, Ang Li, Jing Zhang, Song Xue, Xiaodong Sun
Summary: This study designed and successfully synthesized six tartaric acid-based IL-type chiral selectors, which demonstrated good enantioseparation performance in chiral capillary electrophoresis. Among them, [BMPIP](2)-L-TT showed the best performance, indicating the significant role of cations in enantiorecognition process.
SEPARATION AND PURIFICATION TECHNOLOGY
(2021)
Article
Chemistry, Physical
Vinod Kumar
Summary: Ionic liquids (ILs) provide a unique solvation environment due to their ionic nature, affecting the photophysical properties of 2-Naphthoic acid (2NA) in different IL-based media. The fluorescence emission from 2-Naphthoate anion can be influenced by the presence of [bmim](+) cation in ILs, leading to quenching or complex formation. Specific conditions, such as pH levels and buffer solutions, can also impact the fluorescence behavior of 2-Naphthoic acid in ILs.
JOURNAL OF MOLECULAR LIQUIDS
(2021)
Article
Chemistry, Physical
Yassine Riadi, Oussama Ouerghi, Mohammed H. Geesi, Abdellah Kaiba, El Hassane Anouar, Philippe Guionneau
Summary: In this study, new benzoxazole-linked pyrrolidinone heterocyclic compounds were synthesized using an eco-efficient strategy with a metal-free deep eutectic solvent. The DES, prepared with a eutectic mixture of urea and a synthesized glycine-derived ionic liquid, showed advantages of high productivity, short reaction time, and easy separation for recycling.
JOURNAL OF MOLECULAR LIQUIDS
(2021)
Article
Biochemistry & Molecular Biology
Komal Kumar, Mukesh Kumar, Sreedevi Upadhyayula
Summary: This study successfully synthesized Brønsted acidic ionic liquid catalysts for the conversion of glucose into levulinic acid, with [C(4)SO(3)HPhim][Cl] catalyst showing the highest activity.
Article
Environmental Sciences
Matilde Vieira Sanches, Rosa Freitas, Matteo Oliva, Angelica Mero, Lucia De Marchi, Alessia Cuccaro, Giorgia Fumagalli, Andrea Mezzetta, Greta Colombo Dugoni, Monica Ferro, Andrea Mele, Lorenzo Guazzelli, Carlo Pretti
Summary: The traditional use of organic solvents is being rethought due to their high volatility, toxicity, and interaction with biological membranes. Green Chemistry focuses on developing sustainable and cost-effective solvent alternatives such as Ionic Liquids (ILs), bio-based solvents, and natural deep eutectic solvents (NADESs). This study screened 15 NADESs for ecotoxicity using marine and freshwater bioassays, finding no toxicity to invertebrates but potential biostimulation effects on algae. However, the intentional or accidental release of NADESs into aquatic systems may pose risks to ecosystem functioning.
ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH
(2023)
Article
Chemistry, Applied
Valeria Vanoli, Sara Delleani, Mose Casalegno, Fabio Pizzetti, Pooyan Makvandi, Havard Haugen, Andrea Mele, Filippo Rossi, Franca Castiglione
Summary: Hydrogels based on hyaluronic acid and agarose-carbomer have attracted attention as drug delivery systems. The structure of the polymer network greatly affects the release capability of these materials. Using HR-MAS NMR spectroscopy, this study investigated the motion of drugs within the hydrogels and found evidence of superdiffusive motion, which may be responsible for the faster release of sodium salicylate.
CARBOHYDRATE POLYMERS
(2023)
Article
Biochemistry & Molecular Biology
Elisa Sturabotti, Fabrizio Vetica, Giorgia Toscano, Andrea Calcaterra, Andrea Martinelli, Luisa Maria Migneco, Francesca Leonelli
Summary: A study was conducted on the amidation conditions of N-acetyl-l-phenylalanine using TBTU and various bases for the synthesis of NAPA, a potential drug for joints diseases. The diastereoselective amidation reaction with 1,3,4,6-tetra-O-acetyl-beta-d-glucosamine showed racemization, but the use of pyridine as base showed potential for reducing racemization. Stereochemical retention under amidation conditions was studied in detail through control experiments.
Article
Engineering, Environmental
Alberto Mannu, Maria Enrica Di Pietro, Giacomo Luigi Petretto, Zoubida Taleb, Abdelhak Serouri, Safia Taleb, Alessandro Sacchetti, Andrea Mele
Summary: This study explored the treatment of used vegetable oil using seven different adsorbents and two different procedures. Significant differences were observed in density, turbidity, electrical resistance, free fatty acids (FFAs) content, and relative fatty acid distribution. The results varied depending on the adsorbent and procedure used.
WASTE MANAGEMENT & RESEARCH
(2023)
Article
Chemistry, Organic
Celine Olivier, Nao Nagatomo, Tadashi Mori, Nathan McClenaghan, Gediminas Jonusauskas, Brice Kauffmann, Yutaka Kuwahara, Makoto Takafuji, Hirotaka Ihara, Yann Ferrand
Summary: The synthesis and characterization of a novel pi-extended cationic azahelicene with ten aromatic fused rings are reported. The cationic nature of the compound allows solubility in both organic and aqueous media, enabling photophysical studies in solvents of different polarities. Chiral resolution of the racemate produces two optically pure and configurationally stable enantiomers, exhibiting multi-band circular dichroism and long-wavelength circularly polarized emission in both organic and aqueous media.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Matteo Busato, Giorgia Mannucci, Lorenzo Augusto Rocchi, Maria Enrica Di Pietro, Angela Capocefalo, Elisa Zorzi, Paolo Postorino, Daniele Veclani, Franca Castiglione, Andrea Martinelli, Andrea Martinelli, Paolo Postorino, Paola D'Angelo
Summary: An in-depth study was conducted on the hydrophobic eutectic mixtures formed by l-menthol with BHT, TBC, and PC compounds. Thermal characterization revealed that the BHT/MEN system behaved as an ideal eutectic, while the TBC/MEN and PC/MEN mixtures exhibited the properties of type V deep eutectic solvents. The formation of hydrogen-bond interactions in the BHT/MEN mixtures was hindered due to steric hindrance in the BHT molecule, whereas the TBC-MEN and PC-MEN mixtures were driven by the donor-receptor H-bond and self-association through H-bonded networks, respectively. This study provides valuable insights into the structure-properties relationship of deep eutectic solvents.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Materials Science, Multidisciplinary
Reiya Nishi, Yuki Ishida, Hiroaki Mizuno, Susumu Kawauchi, Gaku Fukuhara
Summary: Permethylated cyclodextrin-polymer conjugates achieved highly sensitive signal amplification detection of angiotensins I-IV and xenopsin-related peptide 2 in aqueous media through positive cooperativity or homotropic allosterism. Microenvironmental solvation and synchronous cooperative complexation were found to play critical roles during the amplification events. The functional chemosensors developed in this study are an attractive alternative to conventional host/receptor molecules.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Materials Science, Multidisciplinary
Hiroki Kurohara, Yumiko Hori, Munenori Numata, Gaku Fukuhara
Summary: This study presents a method for oligosaccharide sensing using fluorophore-probed curdlan. The results demonstrate that the fluorescence signal can be outputted by the aggregation-induced emission of the tetraphenylethylene (TPE) chromophore upon the addition of the target oligosaccharide acarbose. Among the tested saccharides, the TPE-Cur chemosensors exhibit both high sensitivity and excellent selectivity towards acarbose. Morphological studies reveal the important role of globule-to-coaggregation conversion in the optical properties when oligosaccharides interact with the dynamic hydrogen-bonding networks of curdlan chains. This study provides new perspectives for saccharide-responsive materials as attractive alternatives to conventional chemosensors that are difficult to detect in aqueous media.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
G. de Araujo Lima e Souza, M. E. Di Pietro, V. Vanoli, W. Panzeri, F. Briatico-Vangosa, F. Castiglione, A. Mele
Summary: Hydrophobic non-ionic eutectogels (HEG) were prepared from hydrophobic non-ionic (type V) eutectic solvents (HES) using a simple one-pot procedure and a low-cost low molecular weight gelator. The gels were stable and homogeneous, and exhibited increased diffusive motion compared to pure HES, indicating potential applications for solid-like yet mobile systems.
MATERIALS TODAY CHEMISTRY
(2023)
Article
Pharmacology & Pharmacy
Andrea Fiorati, Francesca Baldassarre, Laura Riva, Stefano Tacconi, Concetta Nobile, Viviana Vergaro, Roberto Grisorio, Lucio Melone, Andrea Mele, Luciana Dini, Carlo Punta, Giuseppe Ciccarella
Summary: In this study, a spray drying process was used to produce nanostructured microsponges from TEMPO oxidized cellulose nanofibers (TOCNF). Different formulations were prepared by adjusting the oxidation degree of the nanofibers and the ratios of crosslinkers. The microsponges obtained from TOCNF with the highest carboxylic group content showed good colloidal stability and desired particle size. The microsponges were chemically characterized and exhibited pH-responsive swelling and drug release behavior. Moreover, the microsponges derived from formulations without citric acid were found to be biocompatible based on in vitro tests on gastric cancer cells.
JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY
(2023)
Article
Polymer Science
Soshi Wakako, Yumiko Hori, Tomokazu Kinoshita, Takao Saiki, Xinyi Qi, Koki Hasegawa, Yoshitane Imai, Tadashi Mori, Keiichi Nakagawa, Gaku Fukuhara
Summary: In this study, a series of pyrene-labeled alpha- and epsilon-poly-l-lysine conjugates were synthesized and showed promising performance in sensing, imaging, and drug delivery. The materials demonstrated diverse ratiometric responses to hydrostatic pressure and offered valuable insights into the development of smart hydrostatic-pressure-responsive polymer materials.
Article
Chemistry, Multidisciplinary
Hiroaki Mizuno, Hironobu Nakazawa, Makoto Harada, Yumi Yakiyama, Hidehiro Sakurai, Gaku Fukuhara
Summary: In this study, it was discovered that a pristine buckybowl, sumanene, is capable of forming solution-state supramolecular polymers. It was also demonstrated that sumanene supramolecular polymers can be dynamically controlled by external stimuli, with solvation playing a significant role. This study not only provides new guidelines for the rational design of supramolecular polymers, particularly those utilizing buckybowls, but also unveils interesting dynamic behaviors of supramolecular polymerization.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Daiki Asanuma, Hieu Thi Minh Nguyen, Zuoyue Liu, Sachiko Tojo, Hajime Shigemitsu, Minoru Yamaji, Kiyohiko Kawai, Tadashi Mori, Toshiyuki Kida, Guillem Pratx, Mamoru Fujitsuka, Yasuko Osakada
Summary: We demonstrate a new design for nano-sized scintillators, wherein polymer dots doped with thermally activated delayed fluorescence (TADF) molecules exhibit blue radio-luminescence upon hard X-ray and electron beam irradiation.
NANOSCALE ADVANCES
(2023)
Article
Chemistry, Multidisciplinary
Tomokazu Kinoshita, Shunta Nakamura, Makoto Harada, Taku Hasobe, Gaku Fukuhara
Summary: This study aims to control exciton formation in a pentacene dimer through intramolecular singlet fission (SF) using hydrostatic pressure as an external stimulus. The use of hydrostatic pressure accelerates the SF dynamics and shortens the triplet lifetime, providing a new perspective for controlling SF-based materials. The findings suggest that hydrostatic pressure can be an attractive alternative to conventional control strategies.
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)