Article
Chemistry, Organic
Asim Kumar Swain, Kubandiran Kolanji, T. Christoph Stapper, Prince Ravat
Summary: This paper describes the stereospecific synthesis and functional properties of C-2- and C-1-symmetric pyrene-fused [5]helicene molecules connected via hexagonal and heptagonal rings. The molecules exhibited high configurational stability and unique functional properties due to the fusing mode of [5]helicene with pyrene and molecular symmetry. The estimated Gibbs activation energy for enantiomerization of one of the molecules was among the highest reported values for any p-conjugated molecules incorporating [5]helicene moiety.
Article
Chemistry, Multidisciplinary
Yogesh Kumar Maurya, Pingchun Wei, Takahide Shimada, Kazuhisa Yamasumi, Shigeki Mori, Ko Furukawa, Hajime Kusaba, Tatsumi Ishihara, Yongshu Xie, Masatoshi Ishida, Hiroyuki Furuta
Summary: A facile synthetic strategy has been established for chiral chromophores based on dimeric porphyrinoids, forming a unique class of face-to-face intramolecularly interlocked corrole dimers upon treatment with copper(II) ions. The modulation of their intrinsic electronic structures by peripheral corrole ring annulations results in distinct optical properties and redox profiles. The presence of stereogenic carbon centers in the corrole skeleton provides a rationale for designing novel chiral materials.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Review
Chemistry, Multidisciplinary
Prince Ravat
Summary: The interconversion of enantiomers is a key stereodynamic feature of carbo[n]helicenes, with the Gibbs activation energy determining their configurational stability. This minireview provides an overview of the mechanism, recent developments, and factors affecting the enantiomerization of [n]helicenes, aiming to accelerate the design process of configurationally stable functional chiral molecules based on helicene substructures. Additionally, misconceptions and irregularities in the recent literature on terms such as racemization and enantiomerization, as well as the calculation of activation parameters for [n]helicenes and related compounds, are addressed.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Inorganic & Nuclear
Philipp C. Stegner, Jonathan Eyselein, Gerd M. Ballmann, Jens Langer, Jochen Schmidt, Sjoerd Harder
Summary: The chiral building block (R)-(+)-2,2 '-diamino-1,1 '-binaphthyl, (R)-BINAM, was converted to N-substituted proligands and alkaline earth metal catalysts. Quadrant models analysis showed that ligands with specific substituents provided the best steric discrimination in enantioselective intramolecular alkene hydroamination reactions.
DALTON TRANSACTIONS
(2021)
Article
Materials Science, Multidisciplinary
Jinming Ge, Taipu Chen, Xiaofeng Wan, Lingfeng Lu, Ziqiang Liu, Shucheng Sun, Yuanqin Zhu
Summary: This study designed and synthesized an aromatic monomer-based anion exchange membrane with bulky aryl unit and symmetric dibrominated branches. The membrane, prepared via superacid-catalyzed polyhydroxyalkylation and Menshutkin reactions, showed high hydroxide conductivity and dimensional stability. It also exhibited high alkaline stability and achieved a peak power density of 407.8 mW cm(-2) in H-2-O-2 fuel cells. This work provides insights into the development of high-performance next-generation anion exchange membranes.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Materials Science, Multidisciplinary
Yong-Hui Zhou, Ai-Wei Zhang, Ru-Jun Huang, Yu-Hang Sun, Zhu-Jun Chen, Bai-Song Zhu, You-Xuan Zheng
Summary: Chiral luminescent materials have experienced rapid development in recent years due to their ability to emit circularly polarised luminescence (CPL) for various applications. In this study, three chiral copper(i) chloro-bridged dimers based on R/S-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene ligands were conveniently synthesized with high yields. The dimers exhibited strong luminescence in powder form and doped films, and showed thermally activated delayed fluorescence characteristics. Additionally, the dimers displayed mirror symmetric circular dichroism and CPL spectra, and when used in circularly polarised organic light-emitting diodes (CP-OLEDs), achieved a high maximum external quantum efficiency of 21.7%.
JOURNAL OF MATERIALS CHEMISTRY C
(2023)
Article
Chemistry, Medicinal
Harold Cruz, Felipe A. Servin, Gerardo Aguirre, Sergio Perez, Domingo Madrigal, Daniel Chavez, Andrew L. Cooksy, Ratnasamy Somanathan
Summary: Herein, we describe the synthesis and application of enantiopure C-2-symmetric primary amine-1,3-bis-thiourea organocatalysts for the enantioselective conjugate 1,4-Michael addition reaction. The use of supramolecular noncovalent interactions between the catalyst and the substrate, through hydrogen bonding, lowers the transition state energy, mimicking an enzyme. The experimental results are supported by theoretical calculations.
Article
Chemistry, Multidisciplinary
Ming Cui, Zhi-Yuan Zhao, Martin Oestreich
Summary: Chiral bis(phosphine) monooxides derived from C-2-symmetric bis(phosphines) have been found to exhibit superior enantioselection in copper-catalyzed conjugate borylation and 1,6-addition reactions. Specifically, (R,R)-Bozphos ligand shows significantly higher enantiomeric excesses and chemical yields compared to parent (R,R)-Me-Duphos ligand.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Maksim J. Navakouski, Halina Zhylitskaya, Piotr J. Chmielewski, Marika Zyla-Karwowska, Marcin Stepien
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Liliia Moshniaha, Marika Zyia-Karwowska, Joanna Cybinska, Piotr J. Chmielewski, Ludovic Favereau, Marcin Stepien
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Bartosz Szyszko, Monika Przewoznik, Michal J. Bialek, Agata Bialonska, Piotr J. Chmielewski, Lechoslaw Latos-Grazybski
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Ewelina Janiga, Gakhyun Kim, Piotr J. Chmielewski, Tadeusz Lis, Dongho Kim, Marcin Stepien
CHEMISTRY-AN ASIAN JOURNAL
(2020)
Article
Chemistry, Organic
Sunit Kumar, Yogesh Kumar Maurya, Seongsoo Kang, Piotr Chmielewski, Tadeusz Lis, Joanna Cybinska, Dongho Kim, Marcin Stepien
Article
Chemistry, Organic
Demin Ren, Oskar Smaga, Xinliang Fu, Xiaofang Li, Milosz Pawlicki, Sebastian Koniarz, Piotr J. Chmielewski
Summary: In this study, aromatic zwitterionic corrole nickel(II) complexes were synthesized via a three-component reaction, while a nonaromatic chiral adduct of zwitterionic phlorine character was obtained under certain conditions. This research provides a new perspective for the synthesis of related complexes.
Article
Chemistry, Multidisciplinary
Bibek Prajapati, Duy-Khoi Dang, Piotr J. Chmielewski, Marcin A. Majewski, Tadeusz Lis, Carlos J. Gomez-Garcia, Paul M. Zimmerman, Marcin Stcpieit
Summary: The study presents a hexaradicaloid molecule with alternating Kekule and non-Kekule connectivities, showing a singlet ground state with significant hexaradicaloid character. It exhibits multiple thermally accessible high-spin states and undergoes two consecutive one-electron oxidations at low potentials. This design strategy provides a new approach for multistate spin switches and redox-amphoteric NIR dyes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Shivaprasad Achary Balahoju, Yogesh Kumar Maurya, Piotr J. Chmielewski, Tadeusz Lis, Mateusz Kondratowicz, Joanna Cybinska, Marcin Stepien
Summary: Peripheral substitution of a pi-extended porphyrin with bulky groups can control its curvature and stereochemistry. The coordination of large metal ions and the variation of substituents and ligands affect this control. Experiments have shown that stable enantiopure porphyrin propellers can be synthesized by adjusting experimental conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yogesh Kumar Maurya, Piotr J. Chmielewski, Joanna Cybinska, Bibek Prajapati, Tadeusz Lis, Seongsoo Kang, Seokwon Lee, Dongho Kim, Marcin Stepien
Summary: A family of tunable halochromic switches is developed using a naphthalimide-fused dipyrrin as the core pi-conjugated motif. The electronic properties of these switches can be tuned by substitution of aryl groups with different donor-acceptor strengths. Protonation results in conformational changes and enhanced electronic coupling, leading to halochromic effects and absorption switching between NIR-I and NIR-II ranges. Additionally, selected switches demonstrate a NIR-II photothermal effect switchable by acid-base chemistry.
Article
Chemistry, Multidisciplinary
Sha Li, Yahan Sun, Xiaofang Li, Oskar Smaga, Sebastian Koniarz, Milosz Pawlicki, Piotr J. Chmielewski
Summary: A new series of aromatic porphyrinoids was synthesized by inserting primary amines into the antiaromatic ring of 5,14-dimesityl-norcorrolatonickel(ii) activated by iodosobenzene. The resulting substituted 10-azacorroles were analyzed using spectroscopic and electrochemical methods, as well as XRD analysis. Protonated forms of azacorroles were found to retain aromaticity despite the disruption of the original pi-electron delocalization pathway.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Sebastian Koniarz, Kinga Szydelko, Michal J. Bialek, Karolina Hurej, Piotr J. Chmielewski
Summary: A family of transition metal complexes based on meso-aryl-2-aza-21-carbaporphyrin (N-confused porphyrin, NCP) derivatives were synthesized and characterized. The chirality of these complexes was demonstrated by enantiomeric separation and analysis. Preliminary catalytic study showed the activity of iridium(III) ortho-metallated complexes in the N-heterocyclization of primary amines with diols.
Article
Chemistry, Multidisciplinary
Sha Li, Yahan Sun, Xiaofang Li, Oskar Smaga, Sebastian Koniarz, Marcin Stepien, Piotr J. Chmielewski
Summary: A 1,3-cycloaddition reaction between 2-(tert-butyl)-8H-isoquinolino[4,3,2-de]phenanthridin-9-ium chloride and Ni-II norcorrole in the presence of base has been demonstrated to yield a family of chiral derivatives fused with pyrrole subunits of the macrocycle. Dehydrogenation of the cycloaddition products leads to dibenzoullazine ortho-fused antiaromatic porphyrinoids.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Joanna Hager, Seongsoo Kang, Piotr J. Chmielewski, Tadeusz Lis, Dongho Kim, Marcin Stepien
Summary: In this study, a series of pi-extended dibenzoullazines containing an acenaphthylene subunit were successfully synthesized using two different synthetic strategies. These compounds exhibit strong fluorescence and moderate solvatochromism, making them potentially useful in various applications. Additionally, a chiral ullazine analogue with axial chirality was discovered and successfully resolved into enantiomers.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Sha Li, Oskar Smaga, Yahan Sun, Xiaofang Li, Milosz Pawlicki, Marzena Sukniewicz, Piotr J. Chmielewski
Summary: The reaction of acyl chlorides with norcorrolatonickel(ii) in dichloromethane in the presence of AlCl3 at room temperature yields two isomeric monoketone derivatives, with diketones also detected and separated in the case of acetyl chloride. Spectroscopic and electrochemical characterization studies were supported by DFT calculations.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Demin Ren, Sebastian Koniarz, Xiaofang Li, Piotr Jan Chmielewski
CHEMICAL COMMUNICATIONS
(2020)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
