Article
Chemistry, Multidisciplinary
Pavle Troselj, Peter Bolgar, Pablo Ballester, Christopher A. Hunter
Summary: Melamine oligomers with triazine-piperidine units and phenol/phosphine oxide side-chains form H-bonded duplexes that are stable with increasing chain length. NMR spectroscopy shows no intramolecular folding, while isothermal titration calorimetry reveals that sequence complementary duplexes are significantly more stable than those with single base mismatches. These systems show high-fidelity duplex formation and are promising targets for further investigation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Biochemistry & Molecular Biology
Keisuke Uematsu, Chikara Hayasaka, Ko Takase, Keiichi Noguchi, Koji Nakano
Summary: This study reported a method to synthesize [7]helicenes and [7]helicene-like compounds from thia[7]helicene as a common starting material, including silole- and phosphole-fused compounds, cyclopentadiene-fused compounds, and aza[7]helicenes. The synthesized compounds showed unique absorption and emission properties, with slightly red-shifted absorption for silole-fused compounds and strong violet emission for cyclopentadiene-fused compounds and aza[7]helicenes. Additionally, aza[7]helicenes displayed circularly-polarized luminescence with specific dissymmetry factors.
Article
Chemistry, Multidisciplinary
Jingyun Tan, Xiushang Xu, Jun Liu, Serhii Vasylevskyi, Zesen Lin, Ryota Kabe, Yingping Zou, Klaus Muellen, Akimitsu Narita, Yunbin Hu
Summary: An unprecedented p-extended double [9]helicene has been reported, with its structure unequivocally revealed by single-crystal X-ray diffraction. This helicene exhibits remarkable near-infrared emission from 750 to 1100 nm, along with a high photoluminescence quantum yield of 18%. Optically pure D9H also displays panchromatic circular dichroism with a notable dissymmetry factor (g(CD)) of 0.019 at 590 nm, which is one of the highest reported for helicenes in the visible region.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Kyle R. Strom, Jack W. Szostak
Summary: In this study, six oligoarylacetylene trimers composed of aniline and benzaldehyde subunits were examined, and it was found that reversible covalent bonds could guide the formation of different structures in sequence-defined oligomers. The proportions of these structures could be controlled by the concentration of trimers and an acid catalyst.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Nanoscience & Nanotechnology
Yang Yu, Le Wang, Chang Wang, Fei Liu, Haifeng Ling, Junzhi Liu
Summary: An intramolecular alkyne aromatization reaction is described, leading to the synthesis of two structural isomers, expanded [9]helicene (1) and π-extended double [4]helicene (2), through trifluoroacetic acid-promoted cyclization. The geometric and optoelectronic properties of these isomers are comprehensively investigated, and they show potential as molecular floating gate materials in OFET-NVM devices. The nonplanar geometry of the isomers significantly affects their charge-trapping behaviors, with the 1-based device displaying larger memory window and charge-trapping density compared to the 2-based device. This study highlights the importance of controlling the geometry of molecular nanocarbons for applications in organic electronics.
Article
Chemistry, Multidisciplinary
Ming-Guang Rong, Junting Wang, Junzhi Liu
Summary: A novel zigzag-edged nanographene containing a [7]helicene subunit was designed and synthesized, and its structure and properties were characterized. The study of photophysical properties and electrochemical properties provides new insights for the synthesis of helical nanographenes with rich zigzag edges.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Physical
Xiaozhen He, Fuwei Gan, Yan Zhou, Yuanliang Zhang, Peipei Zhao, Bingru Zhao, Qianyun Tang, Li Ye, Jun Bu, Junyang Mei, Ling Du, Huili Dai, Huibin Qiu, Peifeng Liu
Summary: Helicenes exhibit anticancer capability by changing molecular structure, with nonplanar helicenes showing increased cytotoxicity and cancer inhibition against RCC cells. Benzo[4]helicenium selectively damages RCC cancer cells' mitochondria and DNA, indicating potential as a targeted drug for RCC treatment.
Article
Chemistry, Organic
Florian Rigoulet, Albert Artigas, Nawal Ferdi, Michel Giorgi, Yoann Coquerel
Summary: This study demonstrates that stereochemistry is a critical factor in the reactivity of non-planar polycyclic aromatic hydrocarbons.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Multidisciplinary
Max Lubberink, William Finnigan, Sabine L. Flitsch
Summary: Amide bonds are commonly formed in the pharmaceutical industry and there is a growing interest in biocatalytic methods for their synthesis. The use of low water systems and ATP-dependent enzymes have shown promise in driving amide bond formation. A publicly available database, RetroBioCat, has been compiled to provide literature on these methods.
Article
Chemistry, Multidisciplinary
Liu-Pan Yang, Hua Ke, Huan Yao, Wei Jiang
Summary: The study introduces two amide naphthotube-crosslinked polymers that can effectively remove polar organic micropollutants from water through biomimetic molecular recognition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Blessy Rajan, Twinkal M. Chaudhari, Ashutosh Bedekar
Summary: A new aza[7]helicene carboxylic acid was synthesized from carbazole in few simple steps, characterized by spectroscopic techniques and evaluated for its photophysical properties. The structural parameters were compared with theoretical values obtained from computational analysis, and the molecular recognition of the helical isomers with chiral bases was examined by NMR analysis.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Erin E. Deans, Judy L. M. Kotler, Wei-Shao Wei, Timothy O. Street
Summary: This study investigates the interaction between Hsp70 chaperones and client protein proIGF2, revealing that electrostatic attraction plays a crucial role in facilitating the recognition of oligomers.
JOURNAL OF MOLECULAR BIOLOGY
(2022)
Article
Chemistry, Organic
Takuya Murai, Yongning Xing, Mayu Kurokawa, Toshifumi Kuribayashi, Masanori Nikaido, Elghareeb E. Elboray, Shohei Hamada, Yusuke Kobayashi, Takahiro Sasamori, Takeo Kawabata, Takumi Furuta
Summary: A one-pot transformation method has been developed to convert biaryl dicarboxylic acids to (NH)-phenanthridinone derivatives using Curtius rearrangement and subsequent basic hydrolysis. This method is also applicable for preparing optically active amide-functionalized [7]helicene-like molecules. In addition, aza[5]helicene derivatives with a phosphate moiety were obtained as products of the Curtius rearrangement step when chalcogen atoms were present in the substrates. X-ray diffraction analysis revealed that chalcogen-bonding and pnictogen-bonding interactions may contribute to the stabilization of these compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Juraj Malincik, Sudhakar Gaikwad, Juan P. Mora-Fuentes, Marc-Aurele Boillat, Alessandro Prescimone, Daniel Haussinger, Araceli G. Campana, Tomas Solomek
Summary: We have successfully synthesized a helicene carbon nanohoop with a unique structure and characterized its properties using NMR, MS, and X-ray analysis. The helicene carbon nanohoop exhibits chiroptical properties and configurational stability typical for higher helicenes, and also shows pronounced circular dichroism and circularly polarized luminescence.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Biochemistry & Molecular Biology
Sheng Zhang, Ming Bao, Mieko Arisawa, Masahiko Yamaguchi
Summary: In this article, the effect of triangle temperature oscillations on reversible nonequilibrium chemical reactions is described. The concentration oscillations exhibit diverse nonequilibrium phenomena, including equilibrium intersecting, equilibrium noncontact, and equilibrium sliding, when self-catalytic reactions are involved. Both stable and unstable concentration oscillations occur, and they are classified based on the waveforms in concentration/time profiles, hysteresis curves in concentration/temperature profiles, nature of self-catalytic reactions, and their relationships with equilibrium. Experimental examples using reversible association and dissociation reactions of helicene oligomers are shown.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
