Article
Chemistry, Physical
Mihail Lucian Birsa, Henning Hopf, Peter G. Jones, Laura Gabriela Sarbu, Lucian Gabriel Bahrin
Summary: Several new di- and tetracarboxylic [2.2]paracyclophane derivatives were synthesized through Suzuki coupling reactions. One of the products, pp-bis(4-carboxyphenyl)[2.2]paracyclophane (12), reacted with zinc nitrate to form a 2D coordination polymer with zinc-carboxylate paddlewheel clusters linked by cyclophane cores. The zinc center exhibited a five-coordinate square-pyramidal geometry.
Article
Chemistry, Organic
Malgorzata Kwiatkowska, Jaroslaw Blaszczyk, Leslaw Sieron, Piotr Kielbasinski
Summary: A series of enantiomerically pure derivatives were successfully synthesized for the first time, with the stereoselective acetylation performed under kinetic resolution conditions using a series of hydrolytic enzymes. The primary alcohols were successfully resolved into enantiomers with moderate to good enantioselectivity, while the secondary alcohols were found to be unreactive in the presence of enzymes. The absolute configurations of the products were determined by X-ray analysis and chemical correlation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Dan Xu, Wen-Hua Zheng
Summary: Three pairs of planar chiral heteroarenes were synthesized from optically pure 4-amino[2.2]paracyclophane using palladium-catalyzed Buchwald-Hartwig coupling and hypervalent iodine-mediated oxidative cyclization. Among them, one enantiomer of planar chiral azahelicene was found to exhibit significantly stronger circularly polarized luminescence activity compared to the other planar chiral heteroarenes.
Review
Chemistry, Physical
Jin-Ming Teng, Da-Wei Zhang, Chuan-Feng Chen
Summary: The review summarizes the recent research on the application of PCP and its derivatives in CPL, discussing molecular design strategies and categorizing emitters based on their chemical structures, providing practical perspectives and inspiration for future research in CPL.
Article
Polymer Science
Jiangbo Lv, Hang Xiao, Xian He, Zhengzhu Zhu, Menghao Chen, Wenjie Yang, Jianghuai Hu, Ke Zeng, Gang Yang
Summary: A new functionalized cyclophane derivative, DCI-PcP, has been designed and prepared, showing excellent thermal properties and processability.
Article
Chemistry, Organic
Sourav Biswas, Zahra A. Tabasi, Jian-Bin Lin, Yuming Zhao, Graham J. Bodwell
Summary: The research discovered the rearrangement mechanism of cyclopentadienone 7 into cyclophane 6, which was found to occur in two steps with the involvement of ethanol as a solvent molecule according to DFT computational study. Furthermore, the rearrangement could be avoided by generating 7 under mild conditions and using benzynes as dienophiles to afford the targeted cyclophanes 14 and 16, the latter of which exhibits dual fluorescence emission.
Article
Polymer Science
Arielle Mann, Marcus Weck
Summary: This contribution describes the synthesis of a novel unsymmetrical substituted tetraalkoxy[2.2]paracyclophane-1,9-diene and its polymerization to produce copolymers with alternating cis,trans-poly(p-phenylenevinylene)s. The synthesized polymers exhibit unique optical properties.
Article
Chemistry, Organic
Young Eum Hyun, Dnyandev B. Jarhad, Minjae Kim, Ayeon Yang, Gyudong Kim, Hong-Rae Kim, Lak Shin Jeong
Summary: This study reports a concise synthetic route for the key amino sugar intermediate essential for the synthesis of (S)-MC ribonucleosides in a 100% stereoselective manner, and also the first synthesis of enantiomerically pure (S)-MC cytidine 1. These findings are expected to make significant contributions to the field of nucleoside chemistry and provide opportunities for novel nucleoside discovery.
Article
Chemistry, Multidisciplinary
Motoki Tsuchiya, Ryo Inoue, Kentaro Tanaka, Yasuhiro Morisaki
Summary: Planar chiral [2.2]paracyclophane was used as a chiral scaffold to induce twist chirality in the anthracene moiety, resulting in chiroptical properties such as circular dichroism and circularly polarized luminescence. The experimental results were well reproduced by theoretical studies, which also revealed the origin of these properties.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Applied
C. Zippel, Z. Hassan, A. Q. Parsa, J. Hohmann, S. Brase
Summary: The method of kinetic resolution of 4-acetyl[2.2] paracyclophane via ruthenium-catalyzed enantioselective hydrogenation has been successfully realized, providing enantiomerically pure derivatives with high yields, which are useful for the production of chiral compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
Anna-Carin C. Carlsson, Staffan Karlsson, Rachel H. Munday, Matthew R. . Tatton
Summary: Atropisomerism is a stereochemical phenomenon exhibited by molecules with a rotationally restricted sigma bond. Atropisomers exist as a dynamic mixture and can be interconverted without breaking and reforming bonds. They are frequent targets in medicinal chemistry projects due to their axial chirality and unique 3D structures. However, selecting a single atropisomer presents problems such as interconversion and separation challenges. Chromatography, enzymatic or chiral catalysts can be used for separation, but each method has limitations. This Account discusses the successes, failures, and challenges of developing methods for resolution and synthesis of atropisomeric drug candidates.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Organic
Simon Felder, Marie-Leonie Delcourt, Manon H. E. Bousquet, Denis Jacquemin, Rafael Rodriguez, Ludovic Favereau, Jeanne Crassous, Laurent Micouin, Erica Benedetti
Summary: This study describes the synthesis and photophysical characterization of differently substituted planar chiral analogues of PRODAN based on a [2.2]paracyclophane scaffold. Results show that the (chir)optical properties of the new phane compounds strongly depend on their substitution patterns, with more pronounced solvatochromism and clear chiroptical behaviors observed when the substituents are placed on the two rings of the pCp core in a non-co-planar arrangement (pseudo-para derivative), which may facilitate the design of new pCp-based luminophores with finely tuned photophysical properties.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shashank Tewari, Maulik N. Mungalpara, Suraj Patel, Gareth J. Rowlands
Summary: Planar chiral [2.2]paracyclophanes are synthesized through direct C-H arylation of enantiopure oxazolines, offering a convenient route for ligand and chiral material synthesis. Hydrolysis followed by decarboxylative phosphorylation is demonstrated to be an effective method for obtaining enantiopure [2.2]paracyclophane derivatives that were previously challenging to prepare.
Article
Chemistry, Organic
Sourav Biswas, Zahra A. Tabasi, Louise N. Dawe, Yuming Zhao, Graham J. Bodwell
Summary: The synthesis of anti-[1](1,6)naphthaleno[1](1,6)naphthalenophane (3) was achieved through a two-directional contractive annulation of [2.2]paracyclophane. This [1.1]cyclophane exhibits a high strain and structural distortion, but it was found to be unreactive towards cycloaddition partners (TCNE, DMAD) and under UV irradiation.
Article
Chemistry, Applied
Ying-Chen Duan, Ying Gao, Xiao-Xia You, Yong Wu, Yun Geng, Yue-Gang Fu, Zhong-Min Su
Summary: The TADF nature of [2.2]paracyclophane derivatives with spatially conjugated structures was studied, revealing the influence of the conjugated structure on their optical properties. The design of new molecules resulted in potential efficient red-light TADF materials with enhanced radiation rate and decreased internal conversion rate.
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)