Showing papers in "Israel Journal of Chemistry in 2018"
TL;DR: This review summarizes the applications of macrocyclic CB[7], CB[8] and their derivatives as supramolecular platforms that have been developed in recent years within the field of pharmaceutical sciences and biomolecular sciences, and discusses the current challenges and future prospects of this area.
Abstract: Cucurbit[7]uril (CB[7]) and cucurbit[8]uril (CB[8]) are two key members of the cucurbit[n]uril (CB[n]) family of macrocycles. Because of the good water solubility of CB[7] and the unique ternary binding properties of CB[8], these two macrocycles have attracted increasing attentions in recent years. In particular, many promising reports of exciting applications regarding CB[7] and CB[8] have emerged in the pharmaceutical sciences and complexations of biomolecules, which has become one of the most important areas of potential applications of CB[n]s. This review summarizes the applications of macrocyclic CB[7], CB[8] and their derivatives as supramolecular platforms that have been developed in recent years within the field of pharmaceutical sciences and biomolecular sciences, and discusses the current challenges and future prospects of this area.
77 citations
TL;DR: A review of the structural chemistry of metal-organic framework materials with the MIL-53 type structure is given in this article. But the authors focus on the structural properties of the parent structure, and do not discuss the properties associated with the structural breathing effect.
Abstract: We present a review of the structural chemistry of metal‐organic framework materials with the MIL‐53 type structure. This family of materials is well‐known for its structural flexibility, and also the wide variety of metal cations and functional ligands that can be included. This gives rise to a set of multivariate materials and isoreticular analogues, to which isoreticular functionalisation can also be applied. Starting from the parent structure, containing infinite chains of octahedral trivalent metal cations cross‐linked by benzene‐1,4‐dicarboxylate, we illustrate the compositional variety possible: this includes materials that contain tetravalent and divalent cations, mixtures of metal cations, functionalised ligands, expanded structures from extended linkers and inclusion of pendant ligands. We emphasise the crystal chemistry of this group of materials, but will give some examples of properties, particularly those associated with the structural breathing effect of relevance to molecular sieving, and also discuss emerging practical applications.
63 citations
TL;DR: In this paper, the authors focus on mathematical models based on deterministic mass-action kinetics, which are systems of coupled nonlinear differential equations on the positive orthant of a system.
Abstract: The use of mathematical methods for the analysis of chemical reaction systems has a very long history, and involves many types of models: deterministic versus stochastic, continuous versus discrete, and homogeneous versus spatially distributed. Here we focus on mathematical models based on deterministic mass-action kinetics. These models are systems of coupled nonlinear differential equations on the positive orthant. We explain how mathematical properties of the solutions of mass-action systems are strongly related to key properties of the networks of chemical reactions that generate them, such as specific versions of reversibility and feedback interactions.
60 citations
TL;DR: The work demonstrates that acyclic CB[n]-type compounds are nicely pre-organized and therefore retain the essential aspects of the recognition properties of macrocyclic CB,[n] but allow for more straightforward tailoring of structure and solubility that enables a variety of chemically and biologically important applications.
Abstract: This article traces the development of acyclic cucurbit[n]uril-type receptors with a focus on work from the Isaacs group. First, we describe the synthesis of methylene bridged glycoluril dimers capped with aromatic sidewalls which allowed us to probe the interconversion of the S- and C-shaped dimers which is a fundamental step in CB[n] formation. The C-shaped compounds were found to undergo discrete self-assembly (dimerization) in both water and organic solvents which lead us to investigate multicomponent self-sorting systems. We supressed the self-association of 8 by electrostatic repulsion in the putative dimer which allowed expression of its innate molecular recognition properties toward methylene blue and related planar cationic dyes. Longer glycoluril oligomers (trimer-hexamer, acyclic decamer) were prepared by starving the CB[n]-forming reaction of formaldehyde. The longer oligomers (e. g. 15 and 16) bind to alkylammonium ions in water ≈100-fold weaker than macrocyclic CB[n] highlighting the high preorganization of the acyclic but polycyclic framework. We prepared a wide variety of acyclic CB[n] compounds (wall variants, solubilizing group variants, linker variants) based on glycoluril trimer and tetramer. In particular, 26 and 27 have been shown to possess a wide variety of chemically and biologically interesting functions. For example, 26 was used to formulate the insoluble drug Albendazole and treat mice bearing SK-OV-3 xenograft tumors. Compound 27 binds tightly to the neuromuscular blocking agents rocuronium, vecuronium, and cisatracurium and acts as an in vivo reversal agent for these compounds in anesthetized rats. Container 27 was also found to modulate the hyperlocomotive effect of rats that had been treated with methamphetamine. Finally, 38 has been used as a cross reactive component of sensor arrays that are capable of classifying and quantifying cancer related nitroamine and a range of over the counter drugs. Overall, the work demonstrates that acyclic CB[n]-type compounds are nicely pre-organized and therefore retain the essential aspects of the recognition properties of macrocyclic CB[n] but allow for more straightforward tailoring of structure and solubility that enables a variety of chemically and biologically important applications.
55 citations
55 citations
TL;DR: Bambusurils are macrocyclic compounds whose synthesis was first reported in 2010 and have been investigated mainly because of its six-membered homologues' outstanding binding affinities towards inorganic anions in both organic solvents and water.
Abstract: Bambusurils are macrocyclic compounds whose synthesis was first reported in 2010. Since then bambusurils have been investigated mainly because of its six-membered homologues' outstanding binding affinities towards inorganic anions in both organic solvents and water. Here we summarize the most important aspects of bambusuril chemistry. Basic characteristics of bambusurils are presented, followed by details of their synthesis, and a discussion of their supramolecular properties, with an emphasis on binding in water. Potential applications of bambusurils are highlighted at the end of the review.
50 citations
49 citations
45 citations
41 citations
TL;DR: In this paper, a review of aggregation-induced emission (AIE) chromophores for organic electroluminescent diodes is presented, with particular attention on the performance of different emitting devices.
Abstract: The design of innovative and more efficient Aggregation-Induced Emission (AIE) chromophores has kept a very high scientific interest since the first report on 2001. Among the possible applications, the field of the organic electroluminescent diodes (OLEDs) is highly attractive. This review will focus on very recent development in the design of AIE molecules for OLEDs, with particular attention on the performance of different emitting devices. Another key point is the description of the new class of AIE luminogens showing Thermally Activated Delayed Fluorescence (TADF), which appears as possible solution to overcome the limitation of fluorescent dyes employed in electroluminescent devices.
40 citations
TL;DR: Aggregation-induced emission (AIE) fluorophores become emissive in aggregation states with higher signal-to-noise ratio, better photostability and larger Stokes shifts, including the design principle and application in various sensing systems are summarized.
Abstract: Fluorescent probes have been widely investigated for their features of rapid response, easy operation and high sensitivity. Among them, reaction-based fluorescent probes, for their unique reaction-based nature, guarantee them with excellent selectivity, effectively avoiding the possible interference from other chemical and biological species in physiological environment. Conventional reaction-based fluorescent probes are aggregation-caused quenching (ACQ) fluorophores. The application of these kinds of probes are limited for their poor photostability and narrow Stokes shifts. Compared with ACQ fluorophores, aggregation-induced emission (AIE) fluorophores become emissive in aggregation states with higher signal-to-noise ratio, better photostability and larger Stokes shifts. In this review, we summarize the latest developed reaction-based AIE-active probes, including the design principle and application in various sensing systems and give an outlook for the future development of this kind of promising fluorescent probes.
TL;DR: In this article, the TTFTB and several lanthanide ions self-assemble into metal-organic frameworks (MOFs) that exhibit a novel topology, a (3,3, 3,6,6)coordinated net, which features an unusual ligand coordination mode and stacking motif.
Abstract: Tetrathiafulvalene tetrabenzoate (TTFTB) and several lanthanide ions self-assemble into metal-organic frameworks (MOFs) that exhibit a novel topology, a (3,3,3,6,6)coordinated net, which features an unusual ligand coordination mode and stacking motif. The Yb and Lu MOFs are electrically conductive, with pellet conductivity values of 9(7) 3 10 7 and 3(2) 3 10 7 S/cm, respectively. The crystallographically-determined bond lengths indicate partial oxidation of the ligand, with close S · · · S contacts between ligands providing likely charge transport pathways in the material. Magnetometry reveals temperature-independent paramagnetism, consistent with the presence of ligand-based radicals, as well as weak antiferromagnetic coupling between Yb centers. These results illustrate the diversity of MOF structures and properties that are accessible with the TTFTB ligand owing to its electroactive nature, propensity for intermolecular interactions, and conformational flexibility.
TL;DR: The current state of the art from biomimicry and analyte-specific detection to emerging clinical applications is covered, including pillar[n]arene-based ion channels, enzyme-responsive compounds, imaging agents, biofilm inhibiting derivatives, drug complexing and drug-related applications.
Abstract: Macrocyclic chemistry has provided chemists with a wealth of molecular ‘hosts’. Ever since resurgence in the field during the 1970s and 1980s these hosts’ similarities to natural structures, such the active sites of enzymes, have been noted. Latterly there has been great interest in the recently reported pillar[n]arenes. As if to underline the importance of these compounds, exciting applications are starting to emerge, from electrochemical sensors to antimicrobial agents. Novel uses appear destined to have an impact on clinical conditions from Alzheimer’s disease to cancer treatment. In order to demonstrate the impact of pillar[n]arenes across the chemistry-biology interface this review will cover the current state of the art from biomimicry and analyte-specific detection to emerging clinical applications. Examples include pillar[n]arene-based ion channels, enzyme-responsive compounds, imaging agents, biofilm inhibiting derivatives, drug complexing and drug
TL;DR: In this paper, the authors discuss the recent prominent examples reported for electrically conducting metal-organic frameworks (MOFs) with regards to their synthesis, structural and electronic properties and possible applications.
Abstract: Crystalline and porous framework materials with appreciable charge carrier mobility hold promise as a new semiconducting platform. Through the concepts of reticular chemistry, numerous two- and three-dimensional crystalline and porous frameworks with encoded properties enabling significant electrical conductivity are in reach. Prominent members of this group are the metal-organic frameworks (MOFs), which recently created scientific excitement as highly conductive materials. Herein, we discuss the recent prominent examples reported for electrically conducting MOFs with regards to their synthesis, structural and electronic properties and possible applications. We frame our discussion according to structural features of the MOFs, covering both layered 2D and 3D frameworks.
TL;DR: Cucurbit[n]urils have emerged as potential candidates for drug delivery in several areas due to their strong binding interactions and low toxicity.
Abstract: Cucurbit[n]urils (CB[n]s) have emerged as potential candidates for drug delivery in several areas due to their strong binding interactions and low toxicity. More recently, their benefits for a type of cancer treatment termed Photodynamic Therapy (PDT) have been recognized. The outcomes of this therapy rely on better drug delivery strategies and improving overall photoactivity of the drugs, which is where CB[n]s could have a strong impact. The effects of these molecular containers on photoactivity are discussed and new interesting work is highlighted.
TL;DR: In this article, the authors thank financial support by the European Union through the European Research Council (GRC) and the Spanish government through the “Severo Ochoa Program” (grant SEV‐2016‐0683).
Abstract: The authors thank financial support by the European Union through the European Research Council (grant ERC‐AdG‐2014‐671093, SynCatMatch) and the Spanish government through the “Severo Ochoa Program” (grant SEV‐2016‐0683).