Review
Chemistry, Multidisciplinary
Youdi Zhang, Yutong Ji, Yingyue Zhang, Wenqiang Zhang, Helong Bai, Mengzhen Du, Han Wu, Qing Guo, Erjun Zhou
Summary: This paper reviews the recent progress of Y6-derived asymmetric conjugated molecules, with a focus on the relationship between molecular structure, optoelectronic properties, and device performance. It provides a reference for the future design direction and challenges of this type of photovoltaic materials.
ADVANCED FUNCTIONAL MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Ryota Shimotsukue, Kohei Fujii, Yu Sato, Yuki Nagashima, Ken Tanaka
Summary: We have developed a rhodium-catalyzed intermolecular [2+2+2] cycloaddition reaction with excellent selectivity, producing chiral cyclohexadienylamines. The reaction involves the reaction of two arylacetylenes with a cis-enamide or a silylacetylene to yield the desired products with complete regio- and diastereoselectivity and high yields and enantioselectivity. Mechanistic studies suggest the formation of a rhodacyclopentadiene intermediate from the terminal alkynes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Wanlong Xiao, Lichao Ning, Shuang Xin, Shunxi Dong, Xiaohua Liu, Xiaoming Feng
Summary: An efficient catalytic asymmetric [2+2] cycloaddition of allenyl imide and mono- or disubstituted alkenes has been developed. The use of chiral magnesium(II) complex of N,N'-dioxide allows for high yield and excellent enantioselectivity of axially chiral cyclobutenes and four-membered ring-containing spirocycles. This methodology can also be applied for the late-stage modification of biologically active molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Nanoscience & Nanotechnology
Chao Li, Guangkai Lu, Hwa Sook Ryu, Xiaobo Sun, Han Young Woo, Yanming Sun
Summary: In this study, the effect of the electron-withdrawing abilities of terminal groups on the properties of fused-ring electron acceptors (FREAs) was investigated. It was found that rational selection of terminal groups with different electron-withdrawing capabilities is desirable for designing high-performance asymmetric FREAs.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Nanoscience & Nanotechnology
Xin Song, Licheng Hou, Renjun Guo, Qi Wei, Linqiang Yang, Xinyu Jiang, Suo Tu, Ao Zhang, Zhipeng Kan, Weihua Tang, Guichuan Xing, Peter Muller-Buschbaum
Summary: This study investigated the advantages of asymmetric conformation, finding that IPT-2F based on asymmetric conformation exhibits better optoelectronic and morphological properties, better miscibility with the polymer donor, and improved power conversion efficiency in devices.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Article
Chemistry, Multidisciplinary
Yulin Han, Anni Qin, Qian Zhang, Xue Zhang, Hui Qian, Shengming Ma
Summary: The Rh-catalyzed reaction allows for the efficient synthesis of cis-fused bicyclic products with excellent selectivity and tolerance towards synthetically useful functional groups. The proposed mechanism involves the rapid racemization of the allene moiety in the starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Lingpu Meng, Jingjie Yang, Mei Duan, You Wang, Shaolin Zhu
Summary: Regio- and enantioselective hydroarylamination, hydroalkylamination and hydroamidation of styrenes have been developed using NiH catalysis with a simple bioxazoline ligand under mild conditions. A variety of enantioenriched benzylic arylamines, alkylamines and amides can be easily accessed by employing nitroarenes, hydroxylamines and dioxazolones as amination reagents. Chiral induction in these reactions is proposed to proceed through an enantiodifferentiating syn-hydronickellation step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Takeshi Yasui, Rine Tatsumi, Yoshihiko Yamamoto
Summary: In this study, a dual cobalt and photoredox catalysis was utilized for the [2+2+2] cycloaddition of enediynes to produce tricyclic cyclohexadienes with a quaternary bridgehead carbon. The use of a chiral ligand, (S)-Segphos, enabled highly enantioselective reactions, leading to highly enantio-enriched cyclohexadienes.
Article
Chemistry, Multidisciplinary
Changpeng Chen, Wenqing Guo, Deyong Qiao, Shaolin Zhu
Summary: We report a NiH-catalyzed asymmetric migratory hydroalkylation process for the efficient and selective construction of enantioenriched multi-substituted cycloalkanes. Through a dynamic kinetic asymmetric transformation (DYKAT), easily accessible racemic and isomeric mixtures of cycloalkenes could be directly utilized as starting materials, convergently producing highly regio-, diastereo-, and enantioselective chiral 1,2-cis disubstituted cycloalkanes. In addition, prochiral cyclic alkenes can also be employed, delivering chiral 1,2-cis disubstituted cycloalkanes through desymmetrization process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jiandong Liu, Hegui Gong, Shaolin Zhu
Summary: A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, yielding benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction prevent olefinic products from further isomerization or subsequent alkenylation, and catalytic enantioselective hydroalkenylation of styrenes was achieved using a chiral bisoxazoline ligand.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Inorganic & Nuclear
Olaya Bernardo, Silvia Gonzalez-Pelayo, Luis A. Lopez
Summary: The marriage of heterocyclic compounds with ferrocene has been a fruitful field of research, with several ferrocene-embedded heterocyclic compounds reported in recent years. The synergistic combination of properties from both heterocyclic and metallacyclic motifs in fused systems has led to interesting applications, particularly in asymmetric catalysis.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Leipeng Xie, Jimin Liang, Haohao Bai, Xuanyu Liu, Xiao Meng, Yuan-Qing Xu, Zhong-Yan Cao, Chao Wang
Summary: In this paper, a ligand-controlled, directing-group-assisted strategy was reported to promote NiH-catalyzed site-selective hydroamination of unactivated alkenes. Proper bidentate nitrogen-containing ligands were used to achieve good-to-excellent regioselectivity for the synthesis of 1,1-, 1,2-, and 1,3-diamines from the same substrates. Various O-benzoylhydroxylamine electrophiles with different functional groups can be installed via Ni migration or nonmigration. These protocols provide a method for the enantioselective synthesis of valuable 1,2-diamines and 1,3-diamines.
Article
Chemistry, Physical
Lantao Liu, Fangyuan Cheng, Chenxiang Meng, An-An Zhang, Mingliang Zhang, Kai Xu, Naoki Ishida, Masahiro Murakami
Summary: A Pd-catalyzed chemo-, regio-, and enantioselective ring-closing/ring-opening cross coupling reaction has been developed with diverse aryl halide-tethered alkenes and benzocyclobutenols as substrates. This method provides a convenient approach to chiral 2,3-dihydrobenzofurans with excellent enantioselectivities, and has been applied in the concise synthesis of analogues of cannabinoid receptor 2 agonists.
Article
Energy & Fuels
Zemin Wang, Guilong Cai, Jiayu Wang, Mengyang Li, Boyu Jia, Peiyao Xue, Xinhui Lu, Zheng Tang, Guojie Wang, Xiaowei Zhan
Summary: Molecular symmetry has slight effects on the absorption spectra, energy levels, and bandgaps, but notable effects on crystallinity, molecular packing, film morphology, and device performance. F7TC-1- and F7TC-2-based organic solar cells show significantly different power conversion efficiencies, mainly due to differences in molecular packing and film morphology.
Article
Chemistry, Multidisciplinary
Sundaravel Vivek Kumar, Patrick J. Guiry
Summary: We have developed a facile synthetic route for a novel series of imidazolinyl-[2.2]paracyclophanol (UCD-Imphanol) ligands with central and planar chirality. These ligands showed excellent activities and selectivities in asymmetric reactions, leading to enantioenriched pyrrolidines with high yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Isaac G. Sonsona, Andrea Vicenzi, Marco Guidotti, Giorgiana Denisa Bisag, Mariafrancesca Fochi, Raquel P. Herrera, Luca Bernardi
Summary: The study demonstrates the improved selectivity of an asymmetric aldol reaction by replacing part of the catalyst, and identifies the most suitable reaction conditions. However, these conditions seem to be limited to oxindoles bearing a 3-substituent of funapide.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Alessandro Di Girolamo, Filippo Monti, Andrea Mazzanti, Elia Matteucci, Nicola Armaroli, Letizia Sambri, Andrea Baschieri
Summary: This study successfully synthesized five cationic iridium(III) complexes using phenyl-triazole derivatives, including the less explored tris-heteroleptic analogues. The redox and emission properties of the complexes can be effectively tuned by different ligands. The complexes equipped with bipyridine ancillary ligand exhibit reversible redox processes and high emission quantum yields, while the complexes equipped with high-field isocyanide ligands display irreversible redox processes and high-energy emission with low quantum yields.
INORGANIC CHEMISTRY
(2022)
Article
Polymer Science
Veronica Vetri Buratti, Alberto Sanz de Leon, Mirko Maturi, Letizia Sambri, Sergio Ignacio Molina, Mauro Comes Franchini
Summary: Material science plays a crucial role in achieving sustainability through the use of renewable resources and environmentally friendly manufacturing techniques to replace traditional high energy-demanding processes.
Article
Chemistry, Organic
Giorgiana Denisa Bisag, Pietro Pecchini, Michele Mancinelli, Mariafrancesca Fochi, Luca Bernardi
Summary: In this study, the enantioselective aminocatalytic reactions using sulfoxonium ylides for the first time were employed to synthesize the 1,1a,2,7b-tetrahydrocyclopropa[c]chromene scaffold. Several ring-fused derivatives with moderate-to-good yields and enantioselectivities and perfect diastereoselectivity were obtained using an alpha,alpha-diphenylprolinol aminocatalyst. The versatile hemiacetal moiety in the products allowed for various synthetic manipulations.
Article
Chemistry, Multidisciplinary
Chiara Portolani, Giovanni Centonze, Sara Luciani, Andrea Pellegrini, Paolo Righi, Andrea Mazzanti, Alessia Ciogli, Andrea Sorato, Giorgio Bencivenni
Summary: The first catalytic enantioselective and diastereoselective synthesis of atropisomeric hydrazides was achieved using a sequential catalysis protocol, providing a stereodivergent approach to enantioenriched atropisomeric hydrazides. The resulting axially chiral hydrazides were obtained directly from commercially available reagents in high yields and with good stereocontrol, demonstrating the effectiveness of this strategy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Giuliana Giorgianni, Luca Bernardi, Francesco Fini, Fabio Pesciaioli, Francesco Secci, Armando Carlone
Summary: Enantioselective organocatalysis is a significant field in asymmetric catalysis with substantial impact on both academic and industrial settings. By using pregabalin as a case study, this Perspective demonstrates the various approaches of using organocatalysis in tackling reactions involving simple chiral molecules.
Article
Pharmacology & Pharmacy
Simona Camorani, Silvia Tortorella, Lisa Agnello, Chiara Spanu, Annachiara D'Argenio, Roberto Nilo, Antonella Zannetti, Erica Locatelli, Monica Fedele, Mauro Comes Franchini, Laura Cerchia
Summary: This study presents a novel aptamer-based platform for the targeted delivery of siRNA to triple-negative breast cancer cells. By utilizing cell-targeting and internalizing aptamers, this delivery system specifically delivers siRNA to TNBC cells, resulting in efficient suppression of PD-L1 expression.
Article
Biochemistry & Molecular Biology
Mirko Maturi, Chiara Spanu, Andrea Baschieri, Mauro Comes Franchini, Erica Locatelli, Letizia Sambri
Summary: This paper presents a method to covalently link a luminescent Ir-complex onto the surface of MCC, which represents the first incorporation of an organometallic luminescent probe in this biomaterial. The method is easy and sustainable, using a Bronsted-acid ionic liquid as a catalyst. The obtained luminescent cellulose microcrystals exhibit high and stable emissions and maintain their luminescent properties in dry and wet matrices.
Article
Chemistry, Inorganic & Nuclear
Andrea Baschieri, Flavia Aleotti, Elia Matteucci, Letizia Sambri, Michele Mancinelli, Andrea Mazzanti, Enrico Leoni, Nicola Armaroli, Filippo Monti
Summary: A new azaborine ligand was synthesized and used as an alternative to common cyclometalating ligands to obtain neutral phosphorescent iridium(III) complexes. The azaborine ligand induces a larger band gap in the complexes and results in a blue-shifted emission wavelength compared to the naphthalene analogues.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Daniel Pecorari, Emanuele Giuliani, Andrea Mazzanti, Stefano Stagni, Valentina Fiorini, Giulia Vigarani, Francesco Zinna, Gennaro Pescitelli, Michele Mancinelli
Summary: Bis-aryl carbazole borane derivatives with emissive properties and axial chirality were synthesized. The resolution of a thermally stable atropisomeric pair (compound 1b), which has a B-C chiral axis, was achieved using chiral stationary-phase high-performance liquid chromatography (CSP-HPLC). The complete photophysical properties of all compounds were measured and simulated using time-dependent density functional theory (TD-DFT) calculations, and circularly polarized luminescence spectra were obtained for the atropisomers of compound 1b, with their absolute configuration determined by a TD-DFT simulation of the electronic circular dichroism (ECD) spectra.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Giorgiana Denisa Bisag, Pietro Viola, Luca Bernardi, Mariafrancesca Fochi
Summary: The divergent reactivity of D-A cyclopropane under PTC conditions is reported in this study. By reacting 2-arylcyclopropane-1,1-dicarbonitriles 1 with thioacetic acid under different reaction conditions, a ring-opening or decyanation reaction can be achieved. The use of solid Cs2CO3 unexpectedly leads to the synthesis of new D-A cyclopropane derivatives, followed by diastereoselective acetylation, while the use of an aqueous solution of Cs2CO3 results in a typical ring-opening reaction with the formation of S-thiolate products. Therefore, tailored reaction conditions allow for the synthesis of either cyclic or open-chain products in moderate to good yields.
Article
Chemistry, Physical
Flavia Aleotti, Vasilis Petropoulos, Hannah Van Overeem, Michele Pettini, Michele Mancinelli, Daniel Pecorari, Margherita Maiuri, Riccardo Medri, Andrea Mazzanti, Fabrizio Preda, Antonio Perri, Dario Polli, Irene Conti, Giulio Cerullo, Marco Garavelli
Summary: In this study, we investigate the influence of the structural features of photoactive azobenzene derivatives on the behavior of the photoexcited state and the yield of the trans/cis photoisomerization process. Our results demonstrate that intramolecular H-bonds stabilize the trans isomer and hinder the photoisomerization process, while the involvement of the azo group in keto-enol tautomerism promotes productive torsional motion.
JOURNAL OF PHYSICAL CHEMISTRY A
(2023)
Article
Chemistry, Inorganic & Nuclear
Jing Tu, Daniele Veclani, Filippo Monti, Andrea Mazzanti, Letizia Sambri, Nicola Armaroli, Andrea Baschieri
Summary: A new synthetic method has been developed for the preparation of unexpected emissive iridium(iii) complexes (A and B). The structures and reaction mechanisms of these complexes were characterized and analyzed. The findings of higher photoluminescence quantum yield in complex A compared to known analogues provide a potential pathway for the direct synthesis of luminescent complexes.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Chiara Spanu, Simona Camorani, Silvia Tortorella, Lisa Agnello, Mirko Maturi, Mauro Comes Franchini, Laura Cerchia, Erica Locatelli
Summary: This work demonstrates the synthesis of a drug delivery system using casein nanoparticles. These nanoparticles can encapsulate hydrophobic molecules and be modified with aptamers targeting the epidermal growth factor receptor. In vitro analyses on triple-negative breast cancer cells confirm the safety and targeting efficacy of this system.
NEW JOURNAL OF CHEMISTRY
(2022)
