Article
Chemistry, Physical
Hyejin Kwon, Carson J. Bruns
Summary: Researchers have discovered and characterized a family of all-hydrocarbon, all-p-conjugated [n]cycloparaphenylene-PAH host-guest complexes. They have built a theoretical framework to select these complexes and predict their stabilities. This research offers new opportunities for bespoke PAH separation or remediation materials.
Review
Chemistry, Multidisciplinary
Sayan Sarkar, Pablo Ballester, Mark Spektor, Evgeny A. Kataev
Summary: The design of high-affinity synthetic host-guest complexes is crucial for constructing novel supramolecular assemblies, functional materials, molecular probes, artificial signal transduction events, and interfaces with the biological world. This review discusses recent achievements in designing 1:1 host-guest complexes with exceptional stabilities exceeding 10(6) M-1. The relationships between thermodynamic constants and structural parameters are analyzed, and the design features of high-affinity hosts are discussed, considering different solvents and noncovalent interactions for complex stabilization. Hints for future design of synthetic receptors with high affinity and selectivity are provided.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yan-Long Ma, Shi Yan, Xiong-Jie Xu, Hua Cao, Ruibing Wang
Summary: Bioorthogonal chemistry, with its simplicity, high efficiency, and chemo-selectivity, has great potential in pre-targeting applications. Synthetic host-guest pairs, which have small molecular sizes, strong chemical stability, fast conjugation rate, tunable binding affinity, and easy modification, provide a novel non-covalent bioorthogonal tool for pre-targeting. This review provides a comprehensive overview of the development of synthetic host-guest pairs as novel bioorthogonal tools for pre-targeting, serving as a reference for researchers interested in improving pre-targeting.
CHINESE CHEMICAL LETTERS
(2024)
Review
Chemistry, Inorganic & Nuclear
Xi Yang, Di Yuan, Jinhong Hou, Adam C. Sedgwick, Suying Xu, Tony D. James, Leyu Wang
Summary: The field of supramolecular chemistry has rapidly expanded and become highly influential in various areas like biomedicine, energy materials, catalysis, and sensing. The combination of host/guest chemistry with functional inorganic nanoparticles has led to many new applications in drug delivery, bioimaging, and sensing. Recent progress in the development of organic/inorganic supramolecular nano-systems incorporating host/guest chemistry has been summarized, highlighting their applications in drug delivery, biological imaging, and sensing.
COORDINATION CHEMISTRY REVIEWS
(2021)
Review
Chemistry, Multidisciplinary
Peiren Liu, Fang Fang, Haochen Wang, Niveen M. Khashab
Summary: Stimuli-responsive or smart materials have had a significant impact on material science and engineering, thanks to the exponential development of synthetic host molecules (SHMs) and their corresponding host-guest chemistry. This Minireview presents recent advancements in synthetic host-based smart materials, including fabrication strategies and state-of-the-art applications such as adsorption, separation, luminescence, self-healing, and actuation. The role of host-guest chemistry is highlighted throughout to showcase the potential of emerging materials for future economies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Jayashrita Debnath, Michele Parrinello
Summary: The long time scale associated with ligand residence times makes their computation challenging. The recently developed Gaussian mixture based enhanced sampling technique allows for the computation of residence times and enables an understanding of their unbinding mechanism. Guest unbinding often occurs through a series of intermediate states, which can be characterized by the number of water molecules in the binding cavity. In several cases, the residence time is correlated with water trapping times in the cavity.
JOURNAL OF CHEMICAL THEORY AND COMPUTATION
(2022)
Article
Chemistry, Multidisciplinary
Yu Tian, Jie Yang, Zhenjiang Liu, Mingxue Gao, Xiaoning Li, Weilong Che, Manman Fang, Zhen Li
Summary: A new host-guest doping system was developed in this study to achieve turn-on RTP effect through co-crystallization or grinding, creating organic RTP materials with stimulus-responsive characteristics. Multistage stimulus-responsive RTP characteristics were achieved by introducing pyridine group, and anti-counterfeiting printings were realized through various methods, moving RTP materials closer to commercialization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Yunhan Zhao, Bingbing Ding, Zizhao Huang, Xiang Ma
Summary: This study reports a series of simple multi-guest/host organic long persistent luminescence (OLPL) materials with high quantum yield, achieved by doping phenothiazine derivative guest molecules into 9H-xanthen-9-one host matrices. The F-substituted phenothiazine derivative doping system exhibits highly efficient emission with a quantum yield of 46.3% in air. Moreover, these OLPL materials show promising potential for applications in the field of heat resistance due to their high luminescence efficiency at high temperatures.
Review
Chemistry, Multidisciplinary
Xi Yan, Hao Peng, Yuan Xiang, Juan Wang, Lan Yu, Ye Tao, Huanhuan Li, Wei Huang, Runfeng Chen
Summary: Research focus in the field of organic electronics is currently on the design and characterization of purely organic room-temperature phosphorescent (RTP) materials. Host-guest material systems, with the ability to control and modulate properties, are promising candidates for high-performance RTP materials with diverse applications.
Article
Chemistry, Multidisciplinary
Jonathan H. Boyce, Benjamin J. Reisman, Brian O. Bachmann, John A. Porco
Summary: This study reports novel rearrangements of acylphloroglucinols mediated by formic acid to access diverse synthetic acylphloroglucinol scaffolds, with insights on the mechanism provided by Density-functional theory (DFT) analysis. Evaluation of products using multiplexed activity profiling (MAP) identified SASs that suppressed pS6 (Ser235/236) markers of mTOR and ERK signaling pathways activation. These results demonstrate the pharmacological potential of novel chemotypes through biomimetic synthesis and multiplexed activity profiling.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Meagan A. Beatty, Fraser Hof
Summary: Synthetic molecular recognition systems are increasingly utilized in solving applied problems in the life sciences. This tutorial review highlights the programming of host-guest molecular recognition in water, with examples and lessons focused on generalizable themes. It also surveys recent advances in host-guest chemistry within living cells and organisms.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Benita Barton, Danica B. Trollip, Eric C. Hosten
Summary: Two tricyclic fused host systems were synthesized and their complexes with anisole and its isomers were obtained through recrystallization. The first host formed a 2:1 complex with the isomers, while the second host only formed a 2:3 complex with anisole. Thermal analysis showed that the first complex had higher crystal density and thermal stability compared to the second complex.
Article
Chemistry, Physical
Binh Minh Nguyen, Markus Schmid, Johann Kirsch, Albin Cakaj, Wolfgang Bruetting
Summary: The orientation mechanism of nonpolar dyes in various conditions is studied. It is found that the shape anisotropy and temperature ratio are key factors controlling dye alignment. It is also noted that caution must be exercised when using mixed cohost systems with different glass transition temperatures, as the emitter orientation may not follow the effective glass transition temperature of the mixed host.
CHEMISTRY OF MATERIALS
(2023)
Article
Chemistry, Physical
Yunxiang Lei, Wenbo Dai, Gengchen Li, Yongfeng Zhang, Xiaobo Huang, Zhengxu Cai, Yuping Dong
Summary: Small molecular host-guest doped materials have advantages in high-efficiency room-temperature phosphorescence (RTP) due to their diverse structural design and easy preparation. Dynamic RTP materials show excellent characteristics, such as reversibility, quick response, and tunable luminescence ability, making them applicable in cutting-edge technologies. This Perspective summarizes the advances in host-guest doped dynamic RTP materials that respond to external and internal stimuli and provides insights into molecular design strategies and mechanisms. It is highly beneficial for the future intelligent applications of dynamic RTP systems.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Gloria Tobajas-Curiel, Qingqing Sun, Jeremy K. M. Sanders, Pablo Ballester, Christopher A. Hunter
Summary: This study used chemical double mutant cycles to measure the interaction between a N-methyl pyridinium cation and a pi-box in a calix[4]pyrrole receptor. The cation-pi interaction was found to be attractive (-11 kJ mol-1), but it was 7 kJ mol-1 less favorable than the corresponding aromatic interaction with the isosteric but uncharged tolyl group. The same method was also used to measure the interaction of a pi-box in the calix[4]pyrrole receptor with a cationic N-methyl pyridinium group and neutral isosteric analogues in water.
CHEMICAL COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Zoey Warmerdam, Bianca E. Kamba, My-Hue Le, Thomas Schrader, Lyle Isaacs, Peter Bayer, Fraser Hof
Summary: Methylated free amino acids are important targets for host-guest chemistry, with distinct recognition properties compared to methylated peptides and proteins. Different types of anionic hosts were studied for their binding to various methylated amino acids, with acyclic cucurbiturils showing stronger binding and unique selectivity patterns. Molecular modeling helps explain the preferences of the hosts and the overall selectivity patterns.
Article
Chemistry, Physical
Mateo Forjan, Goran Zgrablic, Silvije Vdovic, Marina Sekutor, Nikola Basaric, Piotr Kabacinski, Maryam Nazari Haghighi Pashaki, Hans-Martin Frey, Andrea Cannizzo, Giulio Cerullo
Summary: The ultrafast photochemical reaction of quinone methide (QM) formation from adamantylphenol was monitored in real time using femtosecond transient absorption spectroscopy and fluorescence upconversion in solution at room temperature. The results showed that QM intermediate formed in the ground state with a time constant of around 100 fs, and the absorption band associated with QM persisted and partially overlapped with other contributions. The findings were supported by theoretical studies simulating the reaction pathway and elucidating its mechanism.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Nanoscience & Nanotechnology
Jasna Alic, Ivana Biljan, Zoran Stefanic, Marina Sekutor
Summary: This study provides a detailed investigation into the on-surface self-assembly of fully sp(3)-hybridized molecules. By utilizing scanning tunneling microscopy, computational tools, and x-ray structural analysis, the most favorable on-surface orientations of diamondoid ethers were identified, and the driving forces behind the self-organization process were explained.
Article
Chemistry, Multidisciplinary
Canjia Zhai, Lyle Isaacs
Summary: This study demonstrates the direct macrocyclization of naphthalene monomers with ethyl ester functional groups can deliver prism[5]arene derivatives, which can be deprotected to yield water-soluble prism[5]arenes. The prism[5]arenes showed high affinity with specific dicationic guests driven by non-classical hydrophobic effect, CH center dot center dot center dot pi interactions, and electrostatic interactions. Host H1 exhibits slightly higher affinity towards common guests compared to pillar[6]arene with carboxylic acid functional groups but is less potent than pillar[6]arene with sulfate groups. Therefore, H1 and H3 can be considered for various chemical and biological applications as high-affinity hosts.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Dilanka V. D. Walpita Kankanamalage, Jennifer H. T. Tran, Noah Beltrami, Kun Meng, Xiao Zhou, Pravin Pathak, Lyle Isaacs, Alexander L. Burin, Mehnaaz F. Ali, Janarthanan Jayawickramarajah
Summary: This study introduces a synthetic surrogate called host-guest-driven toehold-mediated strand displacement (HG-TMSD) that utilizes bioorthogonal interactions to control the process of DNA strand displacement. The HG-TMSD method can be finely modulated by changing the structure of the input sequence and can also be regulated by competing small-molecule guests. It can be integrated into functional devices for controlling enzyme activity and detecting specific microRNA.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Physical
Mateo Forjan, Silvije Vdovic, Marina Sekutor, Dani Skalamera, Piotr Kabacinski, Giulio Cerullo
Summary: This study investigates the photochemical reaction pathways of two compounds in the generation of quinone methides. The results indicate different reaction mechanisms on the femtosecond and nanosecond timescales for the two compounds.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
David King, Tatjana Sumanovac, Steven Murkli, Peter R. Schreiner, Marina Sekutor, Lyle Isaacs
Summary: We synthesized quaternary (di)cationic triamantane derivatives G1 and G3 by permethylating the corresponding primary ammonium ions G2 and G4. The complexation behaviors of G1-G4 with CB[7] and CB[8] were examined using H-1 NMR spectroscopy. CB[8] fully encapsulated G1-G4 while CB[7] formed inclusion complexes with G1, G2, and G4 but could not fully encapsulate the central hydrophobic core of G3. The geometries of the CB[n]-guest complexes were determined by analyzing complexation-induced changes in chemical shifts and confirmed using molecular modeling.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jasna Alic, Tomislav Stolar, Zoran Stefanic, Krunoslav Uzarevic, Marina Sekutor
Summary: Diamondoids have shown promise as carbon-based nanomaterial building blocks due to their unique properties and potential for selective functionalization. Through mechanochemical synthesis, diamondoid ethers with different subunits were efficiently prepared, demonstrating the sustainability benefits of this approach compared to conventional methods. Single-crystal X-ray diffraction experiments confirmed the molecular structures of the target products and provided insights into their solid-state interactions.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Multidisciplinary
Adam T. Brockett, Weijian Xue, David King, Chun-Lin Deng, Canjia Zhai, Michael Shuster, Shivangi Rastogi, Volker Briken, Matthew R. Roesch, Lyle Isaacs
Summary: Pillar[6]MaxQ (P6AS) functions as an in vivo sequestration agent for methamphetamine and fentanyl, forming tight complexes with these drugs. P6AS exhibits good in vitro biocompatibility and can ameliorate the hyperlocomotion caused by methamphetamine and fentanyl in mice experiments. P6AS has significant potential for development as a broad-spectrum in vivo sequestration agent.
Article
Chemistry, Physical
Pablo Pinacho, Donatella Loru, Tatjana Sumanovac, Marina Sekutor, Melanie Schnell
Summary: This article reports the synthesis and characterization of three bulky thioethers featuring an adamantyl group connected to a sulfur atom, and compares them with the 1,1'-diadamantyl ether. In addition, the formation of clusters between these thioethers and a water molecule is investigated, providing valuable insights into the sulfur-centered hydrogen bonding in thioethers.
Article
Chemistry, Physical
Marija Aleskovic, Florian Kuestner, Roman Messner, Florian Lackner, Wolfgang E. Ernst, Marina Sekutor
Summary: Diamondoid molecules and their derivatives are versatile building blocks for advanced functional materials. In this study, the self-assembling behavior of diamondoid acids and alcohols in superfluid helium nanodroplets was investigated using mass spectrometry and computational methods. The results provide insights into the different modes of aggregation and cluster structures compared to less-polar diamondoid derivatives. The identified cluster sizes and structures highlight the unique self-organization process driven by hydrogen bonding interactions. The findings offer valuable information for the design of functional materials.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Multidisciplinary
Andrea Usenik, Marija Aleskovic, Suncica Roca, Iva Markus, Marina Sekutor, Josip Pozar
Summary: Understanding the forces governing hydrophobically driven inclusion is crucial for the utilization of non-polar synthons. This study sheds light on the factors determining the stability of complexes with large guests and provides insights into the hydration thermodynamics.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
David King, Chelsea R. Wilson, Lukas Herron, Chun-Lin Deng, Shams Mehdi, Pratyush Tiwary, Fraser Hof, Lyle Isaacs
Summary: In this study, we investigated the molecular recognition properties of P[n]MQ towards (methylated) amino acids, amino acid amides, and post-translationally modified peptides using various techniques. Our findings showed that P6MQ is a strong receptor for N-methylated amino acid side chains, specifically recognizing the H3K4Me(3) peptide with high affinity (K-d = 16 nM) in phosphate buffered saline.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Marija Aleskovic, Suncica Roca, Ruza Jozepovic, Nikola Bregovic, Marina Sekutor
Summary: The formation of inclusion complexes of diamondoid derivatives with cyclodextrins was investigated in this study using various techniques. The results showed that adamantane- and diamantane-based guests formed stable complexes with beta-cyclodextrin, while only the diamantane derivative interacted with gamma-cyclodextrin. The thermodynamics and structural features of these complexes were characterized, providing a comprehensive understanding of the stability effects.
NEW JOURNAL OF CHEMISTRY
(2022)
