Article
Chemistry, Multidisciplinary
Amit Ghosh, Laura Slappendel, Bao-Nguyen T. Nguyen, Larissa K. S. von Krbek, Tanya K. Ronson, Ana M. Castilla, Jonathan R. Nitschke
Summary: A strategy for light-powered guest release from a tetrahedral capsule was developed by introducing azobenzene units at its vertices. The tetrahedral capsule containing 12 diazo moieties at its metal-ion vertices was prepared and could undergo isomerization upon ultraviolet irradiation, leading to guest release. Cage re-assembly and guest re-uptake could be achieved by visible-light irradiation. 19F NMR study provided a detailed understanding of how switching led to guest release.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Susama Chakraborty, Ankana Karmakar, Suraj Mandal, Tamal Goswami, Pranab Ghosh, Amitava Mandal
Summary: The present study focuses on the supramolecular host-guest complexation of OCASP into b-CD, resulting in a thermoresponsive nanotubular architecture. The inclusion complex was characterized using various techniques, and the formation of nanotubes was observed. The reversible switching of assembly and disassembly of the system was demonstrated by temperature changes. Hydrophobic interactions were identified as the main driving force behind the hierarchical structure formation, as confirmed by control experiments. Molecular dynamics simulations further elucidated the stepwise formation process of this hierarchy. This stimuli-responsive system has the potential to tailor its physical properties and contribute to the fabrication of novel smart materials.
JOURNAL OF MOLECULAR LIQUIDS
(2023)
Article
Chemistry, Multidisciplinary
Jianbing Jin, Jiarong Miao, Chuyang Cheng
Summary: A mono-mercapto-functionalized pillar[5]arene and its dimer were synthesized and found to be reversibly interconverted, with a faster reversible redox conversion observed in their host-guest complexes compared to the hosts themselves.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Thomas A. Sobiech, Yulong Zhong, Daniel P. Miller, Jillian K. McGrath, Christina T. Scalzo, Morgan C. Redington, Eva Zurek, Bing Gong
Summary: The article presents experimental results on the binding of a rigid aromatic oligoamide macrocycle with DABCO-based cationic guests in highly polar DMF, demonstrating strong positive cooperativity. The unusually strong positive cooperativity mechanism is verified through various experimental methods. This host-guest system provides a tunable platform for studying molecular interactions and constructing stable supramolecular assemblies due to its exceptional positive cooperativity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Shinnosuke Horiuchi, Takumi Yamaguchi, Jacopo Tessarolo, Hirotaka Tanaka, Eri Sakuda, Yasuhiro Arikawa, Eric Meggers, Guido H. Clever, Keisuke Umakoshi
Summary: In this study, we achieved symmetry-breaking self-assembly of a defined C-1-symmetric supramolecular structure by the synergistic effects of weak binding forces. The flexible capsule framework undergoes a large structural change upon guest binding, forming a distorted resorcin[4]arene hexameric capsule with an asymmetric cavity. The location of the chiral guest in the anisotropic environment leads to modulation of its Electric Dipole (ED) and Magnetic Dipole (MD) transition moments, resulting in increased emission quantum yield and circularly polarized luminescence.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Khaleel Assaf
Summary: The supramolecular complexation of doxepin with cucurbit[7]uril was investigated in aqueous solution, and a host-guest complex was formed. The partial encapsulation of doxepin led to the development of a supramolecular assembly at low concentration.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Weibin Yu, Feng-Yi Qiu, Shi-Ting Luo, Hua-Tian Shi, Guozan Yuan, Xianwen Wei
Summary: Researchers have successfully constructed a triply interlocked [2]catenane with confirmed solid-state structure and solution properties, showing potential applications in drug delivery systems.
INORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Physical
Weilin Qi, Xuejiao Wang, Zeyu Liu, Kaerdun Liu, Yifan Long, Wanwan Zhi, Cheng Ma, Yun Yan, Jianbin Huang
Summary: Through self-assembly experiments, it was found that only ortho-xylene can form hydrogels with cyclodextrin due to its unique molecular conformation, which leads to a stable orientation in the cyclodextrin complex and ultimately gel formation.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2021)
Article
Polymer Science
Fabian Hoeglsperger, Timo Betz, Bart Jan Ravoo
Summary: This study demonstrates the reversible modulation of osmotic pressure in an aqueous solution using photoresponsive materials. By designing suitable compounds, a drastic change in osmotic pressure can be achieved, allowing for the control of solute concentration in the solution.
Article
Polymer Science
Zhanqi Cao, Fan Yang, Dongpu Wu, Lulu Wu, Lijie Liu, Guoxing Liu, Xiaochuan Li, Xin Zheng, Xianfu Zheng, Dahui Qu
Summary: A novel pillar[5]arene-bridged monomer with TPE and nitrile group was synthesized and it formed supramolecular aggregates based on the host-guest interaction. The supramolecular aggregates exhibited significant aggregation-induced emission due to the restricted intramolecular rotation of the TPE core.
Article
Chemistry, Multidisciplinary
Jenny Yuk-Wa Yeung, Fred Ka-Wai Kong, Franky Ka-Wah Hau, Michael Ho-Yeung Chan, Maggie Ng, Ming-Yi Leung, Vivian Wing-Wah Yam
Summary: A series of platinum(II) calix[4]arene-based molecular tweezers were synthesized, and their host-guest association with a charge-neutral cyclometalated platinum(II) complex was studied. The experiments showed that changing the solvent composition could control the assembly process, resulting in the formation of high-ordered host-guest oligomers. The change in assembly behaviors could be detected through drastic color changes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Hyejin Kwon, Brian S. Newell, Carson J. Bruns
Summary: Cycloparaphenylene nanocarbons (CPPs) are organic semiconductors with controllable structures and unique optoelectronic properties. In this study, CH-pi interactions were found to enable the inclusion of redox-active metallocene guests in CPPs, enhancing stability through additional supramolecular forces. This finding is significant for the design of bespoke nanoelectronics and artificial molecular machines.
Article
Chemistry, Inorganic & Nuclear
Edward Britton, Richard J. Ansell, Mark J. Howard, Michaele J. Hardie
Summary: New photoswitchable pyridyl-azo-phenyl-decorated tripodal host ligands (L-az) have been synthesized, showing a remarkable 7-fold Borromean-weave entanglement and forming metallo-cryptophanes cages with less robust photoswitching behavior.
INORGANIC CHEMISTRY
(2021)
Article
Polymer Science
Zhe Huang, Shenghui Rao, Wenjie Fan, Zhaozhao Duan, Yang Bai, Xiaohui Huang, Fenfen Xu, Hui Li
Summary: In this work, three monomers were designed and synthesized to form a supramolecular hyperbranched polymer based on recognition and coordination. The self-organization of the monomers was characterized and the molecular weight of the supramolecular polymer was found to depend on the initial monomer concentration. The resulting polymer exhibited competitive guest responsiveness and enhanced fluorescence emission in the presence of OH-.
Review
Chemistry, Multidisciplinary
Mao Quan, Xin-Yu Pang, Wei Jiang
Summary: Optical methods, particularly Circular dichroism-based chiroptical sensing, show great potential in high-throughput screening for chirality analysis in drug discovery. This emerging field explores molecular recognition, chirality transfer, classification of chirality sensors, and applications in asymmetric reactions and reaction kinetics monitoring. Challenges and research directions in this area are also emphasized.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Efrat Pahima, Qi Zhang, Konrad Tiefenbacher, Dan T. Major
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Multidisciplinary
Severin Merget, Lorenzo Catti, GiovanniMaria Piccini, Konrad Tiefenbacher
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Leonidas-Dimitrios Syntrivanis, Ivana Nemethova, Dario Schmid, Shani Levi, Alessandro Prescimone, Fabian Bissegger, Dan T. Major, Konrad Tiefenbacher
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Fabian R. Bissegger, Markus Neuburger, Konrad Tiefenbacher
SUPRAMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Melina Knezevic, Michael Heilmann, Giovanni Maria Piccini, Konrad Tiefenbacher
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Ivana Nemethova, Leonidas-Dimitrios Syntrivanis, Konrad Tiefenbacher
Article
Chemistry, Organic
Suren J. Nemat, Hanna Jedrzejewska, Alessandro Prescimone, Agnieszka Szumna, Konrad Tiefenbacher
Article
Chemistry, Multidisciplinary
Severin Merget, Lorenzo Catti, Shani Zev, Dan T. Major, Nils Trapp, Konrad Tiefenbacher
Summary: A large hexameric cage based on intermolecular amide-amide dimerization is reported, with a diameter of 2.3 nm and a cavity volume of 2800 Å(3), larger than any previously known capsule/cage structure relying solely on hydrogen bonds. The self-assembly process in chlorinated organic solvents is strongly concentration-dependent, with the monomeric form prevailing at low concentrations. Additionally, the formation of host-guest complexes with fullerenes (C-60 and C-70) was observed.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Suren J. Nemat, Konrad Tiefenbacher
Summary: Three novel thiol-bearing resorcin[4]arene and pyrogallol[4]arene derivatives were synthesized and studied for their properties in self-assembly, disulfide chemistry, and Bronsted acid catalysis. The findings showed that one compound could form a hexameric hydrogen bond-based capsule in self-assembly, another compound could be covalently linked through disulfides, and the increased acidity of aromatic thio-substituent was not sufficient to replace HCl as a cocatalyst for capsule-catalyzed terpene cyclizations.
Article
Chemistry, Organic
Fabian Huck, Lorenzo Catti, Gian Lino Reber, Konrad Tiefenbacher
Summary: Chiral pyrrolidine derivatives are crucial for natural product synthesis, and carbonyl olefin metathesis is a powerful tool for constructing these building blocks. The supramolecular resorcinarene catalyst enables access to chiral 2,5-dihydropyrroles under Bronsted acid catalysis, even tolerating Lewis-basic protecting groups. The product yield and selectivity in this catalytic system depend on the size of the substrates due to reaction occurring inside a closed cavity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jonathan Pfeuffer-Rooschuez, Lucius Schmid, Alessandro Prescimone, Konrad Tiefenbacher
Summary: A new class of macrocycles called xanthene[n]arenes has been synthesized, featuring a conformationally restricted bowl shape that allows for the synthesis of cavitands and self-assembly into molecular capsules via noncovalent interactions. The derivatization potential of these novel macrocycles has been demonstrated, showcasing their ability to serve as a new set of macrocyclic building blocks.
Article
Chemistry, Multidisciplinary
Daria Sokolova, Konrad Tiefenbacher
Summary: This study optimized the reaction conditions for iminium-catalysed 1,4-reductions within a supramolecular resorcinarene capsule, achieving enantioselectivities of up to 92% ee. Additionally, it was discovered that alcohol additives play a dual role in slowing down background reactions and increasing the rate of capsule-catalysed reactions.
Article
Chemistry, Multidisciplinary
Suren J. Nemat, Dietger Van den Eynden, Loren Deblock, Michael Heilmann, Jesper M. Koester, Mahsa Parvizian, Konrad Tiefenbacher, Jonathan De Roo
Summary: Two resorcin[4]arene scaffolds with four phosphate binding groups were designed and synthesized, showing superior binding affinity compared to single phosphonates at low surface coverage, as demonstrated by solution NMR spectroscopy.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Michael Heilmann, Melina Knezevic, GiovanniMaria Piccini, Konrad Tiefenbacher
Summary: A modular synthetic platform for constructing flexible glycoluril-derived molecular tweezers was developed and investigated for their binding properties towards 16 organic amines through H-1 NMR titration. The results demonstrated that certain structural modifications can lead to potent and selective binding of natural polyamines by the molecular tweezers.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Qi Zhang, Lorenzo Catti, Leonidas-Dimitrios Syntrivanis, Konrad Tiefenbacher
NATURAL PRODUCT REPORTS
(2019)
