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Molecules
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Calixarenes, Pillararenes, and Cucurbiturils
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Calixarenes, Pillararenes, and Cucurbiturils

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 August 2017) | Viewed by 37728

Special Issue Editors

Dr. Peter Cragg

E-Mail Website
Guest Editor
School of Pharmacy and Biomolecular Sciences, University of Brighton, Brighton, UK
Interests: supramolecular chemistry; computational chemistry; sensors; Calix[n]arenes; Oxacalix3arene; Pillar5arenes
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Carl Redshaw

E-Mail Website
Guest Editor
Department of Chemistry, University of Hull, Hull, UK
Interests: calixarenes; coordination chemistry’ catalysis; polymers; imaging and anti-cancer agents
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Calixarenes, pillararenes and cucurbiturils are all structurally similar yet versatile macrocycles. Different sizes of each are now readily accessible, and this has allowed their properties to be investigated. Results to date indicated their ability to exhibit useful host-guest properties, which has led to applications in areas such as sensors. Furthermore, these macrocycles can act as ligands and their coordination chemistry is now opening up new avenues of research in catalysis, medicine and beyond. In this Special Issue, we welcome research articles in all areas concerned with these three types of macrocycles and related systems including new synthetic routes, structural aspects and applications.

Dr. Peter Cragg
Prof. Dr. Carl Redshaw
Guest Editors

Manuscript Submission Information

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Keywords

  • calixarene
  • pillararene
  • cucurbituril
  • macrocycles

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Published Papers (6 papers)

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Research

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8 pages, 1590 KiB  
Article
Calixarenes as High Temperature Matrices for Thermally Activated Delayed Fluorescence: C70 in Dihomooxacalix[4]arene
by Tiago Palmeira, Alexandre S. Miranda, Paula M. Marcos and Mário N. Berberan-Santos
Molecules 2018, 23(3), 558; https://doi.org/10.3390/molecules23030558 - 2 Mar 2018
Cited by 4 | Viewed by 4279
Abstract
Thermally activated delayed fluorescence (TADF) of 12C70 and 13C70 was observed up to 140 °C in a p-tert-butyldihomooxacalix[4]arene solid matrix, a temperature range significantly higher than that of previous TADF quantitative studies. An effective singlet–triplet energy gap of [...] Read more.
Thermally activated delayed fluorescence (TADF) of 12C70 and 13C70 was observed up to 140 °C in a p-tert-butyldihomooxacalix[4]arene solid matrix, a temperature range significantly higher than that of previous TADF quantitative studies. An effective singlet–triplet energy gap of 29 kJ/mol and triplet formation quantum yields of 0.97 and 0.99 were measured for 12C70 and 13C70, respectively. The photophysical properties of the two fullerenes in this new matrix are comparable to those obtained in polystyrene at a lower temperature range. Calixarenes are proposed to be suitable matrices for high temperature TADF studies and applications. Full article
(This article belongs to the Special Issue Calixarenes, Pillararenes, and Cucurbiturils)
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13 pages, 2749 KiB  
Article
Comparison of Binding Affinities of Water-Soluble Calixarenes with the Organophosphorus Nerve Agent Soman (GD) and Commonly-Used Nerve Agent Simulants
by Jayne A. Ede, Peter J. Cragg and Mark R. Sambrook
Molecules 2018, 23(1), 207; https://doi.org/10.3390/molecules23010207 - 19 Jan 2018
Cited by 17 | Viewed by 5442
Abstract
The formation of inclusion complexes of the water-soluble p-sulfonatocalix[n]arenes, where n = 4 or 6, with the Chemical Warfare Agent (CWA) GD, or Soman, and commonly used dialkyl methylphosphonate simulants has been studied by experimental solution NMR methods and by [...] Read more.
The formation of inclusion complexes of the water-soluble p-sulfonatocalix[n]arenes, where n = 4 or 6, with the Chemical Warfare Agent (CWA) GD, or Soman, and commonly used dialkyl methylphosphonate simulants has been studied by experimental solution NMR methods and by Molecular Mechanics (MMFF) and semi-empirical (PM6) calculations. Complex formation in non-buffered and buffered solutions is driven by the hydrophobic effect, and complex stoichiometry determined as 1:1 for all host:guest pairs. Low affinity complexes (Kassoc < 100 M−1) are observed for all guests, attributed to poor host–guest complementarity and the role of buffer cation species accounts for the low affinity of the complexes. Comparison of CWA and simulant behavior adds to understanding of CWA–simulant correlations and the challenges of simulant selection. Full article
(This article belongs to the Special Issue Calixarenes, Pillararenes, and Cucurbiturils)
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7 pages, 1718 KiB  
Communication
Host-Guest Interaction of Cucurbit[8]uril with N-(3-Aminopropyl)cyclohexylamine: Cyclohexyl Encapsulation Triggered Ternary Complex
by Yu Xia, Chuan-Zeng Wang, Mengkui Tian, Zhu Tao, Xin-Long Ni, Timothy J. Prior and Carl Redshaw
Molecules 2018, 23(1), 175; https://doi.org/10.3390/molecules23010175 - 15 Jan 2018
Cited by 5 | Viewed by 4911
Abstract
The host-guest interaction of a series of cyclohexyl-appended guests with cucurbit[8]uril (Q[8]) was studied by 1H NMR spectroscopy, isothermal titration calorimetry (ITC), and X-ray crystallography. The X-ray structure revealed that two cycloalkane moieties can be simultaneously encapsulated in the hydrophobic cavity of [...] Read more.
The host-guest interaction of a series of cyclohexyl-appended guests with cucurbit[8]uril (Q[8]) was studied by 1H NMR spectroscopy, isothermal titration calorimetry (ITC), and X-ray crystallography. The X-ray structure revealed that two cycloalkane moieties can be simultaneously encapsulated in the hydrophobic cavity of the Q[8] host to form a ternary complex for the first time. Full article
(This article belongs to the Special Issue Calixarenes, Pillararenes, and Cucurbiturils)
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Graphical abstract

4664 KiB  
Article
Synthesis and Structure of the Inclusion Complex {NdQ[5]K@Q[10](H2O)4}·4NO3·20H2O
by Li Xia Chen, Jing Lan Kan, Hang Cong, Timothy J. Prior, Zhu Tao, Xin Xiao and Carl Redshaw
Molecules 2017, 22(7), 1147; https://doi.org/10.3390/molecules22071147 - 9 Jul 2017
Cited by 9 | Viewed by 5395
Abstract
Heating a mixture of Nd(NO3)3·6H2O, KCl, Q[10] and Q[5] in HCl for 10 min affords the inclusion complex {NdQ[5]K@Q[10](H2O)4}·4NO3·20H2O. The structure of the inclusion complex has been investigated by single crystal X-ray diffraction and by X-ray Photoelectron spectroscopy (XPS). Full article
(This article belongs to the Special Issue Calixarenes, Pillararenes, and Cucurbiturils)
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4400 KiB  
Article
Inclusion Complexes of a New Family of Non-Ionic Amphiphilic Dendrocalix[4]arene and Poorly Water-Soluble Drugs Naproxen and Ibuprofen
by Khalid Khan, Syed Lal Badshah, Nasir Ahmad, Haroon Ur Rashid and Yahia Mabkhot
Molecules 2017, 22(5), 783; https://doi.org/10.3390/molecules22050783 - 11 May 2017
Cited by 13 | Viewed by 5352
Abstract
The inclusion complexes of a new family of nonionic amphiphilic calix[4]arenes with the anti-inflammatory hydrophobic drugs naproxen (NAP) and ibuprofen (IBP) were investigated. The effects of the alkyl chain’s length and the inner core of calix[4]arenes on the interaction of the two drugs [...] Read more.
The inclusion complexes of a new family of nonionic amphiphilic calix[4]arenes with the anti-inflammatory hydrophobic drugs naproxen (NAP) and ibuprofen (IBP) were investigated. The effects of the alkyl chain’s length and the inner core of calix[4]arenes on the interaction of the two drugs with the calix[4]arenes were explored. The inclusion complexes of Amphiphiles 1a–c with NAP and IBP increased the solubility of these drugs in aqueous media. The interaction of 1a–c with the drugs in aqueous media was investigated through fluorescence, molecular modeling, and 1H-NMR analysis. TEM studies further supported the formation of inclusion complexes. The length of lipophilic alkyl chains and the intrinsic cyclic nature of cailx[4]arene derivatives 1a–c were found to have a significant impact on the solubility of NAP and IBP in pure water. Full article
(This article belongs to the Special Issue Calixarenes, Pillararenes, and Cucurbiturils)
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Review

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2594 KiB  
Review
Fluorescence Resonance Energy Transfer Systems in Supramolecular Macrocyclic Chemistry
by Xin-Yue Lou, Nan Song and Ying-Wei Yang
Molecules 2017, 22(10), 1640; https://doi.org/10.3390/molecules22101640 - 29 Sep 2017
Cited by 43 | Viewed by 10986
Abstract
The fabrication of smart materials is gradually becoming a research focus in nanotechnology and materials science. An important criterion of smart materials is the capacity of stimuli-responsiveness, while another lies in selective recognition. Accordingly, supramolecular host-guest chemistry has proven a promising support for [...] Read more.
The fabrication of smart materials is gradually becoming a research focus in nanotechnology and materials science. An important criterion of smart materials is the capacity of stimuli-responsiveness, while another lies in selective recognition. Accordingly, supramolecular host-guest chemistry has proven a promising support for building intelligent, responsive systems; hence, synthetic macrocyclic hosts, such as calixarenes, cucurbiturils, cyclodextrins, and pillararenes, have been used as ideal building blocks. Meanwhile, manipulating and harnessing light artificially is always an intensive attempt for scientists in order to meet the urgent demands of technological developments. Fluorescence resonance energy transfer (FRET), known as a well-studied luminescent activity and also a powerful tool in spectroscopic area, has been investigated from various facets, of which the application range has been broadly expanded. In this review, the innovative collaboration between FRET and supramolecular macrocyclic chemistry will be presented and depicted with typical examples. Facilitated by the dynamic features of supramolecular macrocyclic motifs, a large variety of FRET systems have been designed and organized, resulting in promising optical materials with potential for applications in protein assembly, enzyme assays, diagnosis, drug delivery monitoring, sensing, photosynthesis mimicking and chemical encryption. Full article
(This article belongs to the Special Issue Calixarenes, Pillararenes, and Cucurbiturils)
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