Special Issue "Novel Sensing Materials for Stereoselective Sensors Development and Chiral Pollutant Detection"

A special issue of Chemosensors (ISSN 2227-9040). This special issue belongs to the section "Materials for Chemical Sensing".

Deadline for manuscript submissions: 31 October 2021.

Special Issue Editors

Prof. Dr. Victor Borovkov
E-Mail Website
Guest Editor
1. College of Chemistry and Material Sciences, South-Central University for Nationalities, Wuhan 430074, China
2. Department of Chemistry and Biotechnology, Tallinn University of Technology, Academia tee 15, 12616 Tallinn, Estonia
Interests: sensors; induced chirality; chirality transfer; supramolecular chirality; chiral chromophores; circular dichroism; chiral materials and surfaces
Special Issues and Collections in MDPI journals
Prof. Riina Aav
E-Mail Website
Guest Editor
Department of Chemistry and Biotechnology, School of Science, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
Interests: chiral compounds; synthesis of macrocycles; host-guest chemistry; chirality induction; cucurbiturils
Prof. Dr. Roberto Paolesse
E-Mail Website
Guest Editor
Dept. of Chemical Science and Technologies University of Rome Tor Vergata via della Ricerca Scientifica 1 00133 Rome, Italy
Interests: chemical sensors; porphyrins; corroles; sensor arrays; supramolecular chemistry; nanostructured materials; thin films
Special Issues and Collections in MDPI journals
Dr. Manuela Stefanelli
E-Mail Website
Guest Editor
Department of Chemical Science and Technology (STC), University of Rome “Tor Vergata”, 00133 Rome, Italy
Interests: porphyrinoid synthesis; chiral porphyrin aggregates; chiral materials; stereoselective sensors
Dr. Donato Monti
E-Mail Website
Guest Editor
Department of Chemical Science and Technology (STC), University of Rome “Tor Vergata”, 00133 Rome, Italy
Interests: supramolecular chirality; chiral assemblies; porphyrins; self-aggregation; chiral recognition

Special Issue Information

Dear Colleagues,

Chirality (from the Greek word “kheir", meaning “hand”) is a fundamental concept that has been recognised in chemistry since the second half of nineteenth century. In fact, hard as they try, nobody could ever overestimate its importance, that extends from the synthesis of organic and inorganic compounds, pharmaceutical and biologically active molecules, theoretical studies and technological application, to understanding the basic principles and origin of the emergence of Life on our planet.

A chiral species is a single molecule or molecular assembly that cannot be superimposed with its mirror image. Chiral molecules are consequently present as two stereoisomers, called enantiomers, and, importantly, they are the main building blocks of living organism. On a daily basis, chiral molecules are conventionally used and produced by pharmaceutical, food, agrochemical, perfume, and cosmetics industries. As a result, chiral waste becomes an extremely important issue at present. Chiral compounds can be ecologically hazardous, due to their high biological activity, creating a global pollution problem. It is of note, that enantiomers have a different impact on living organisms making it extremely important to differentiate these stereoisomers, which is extremely a difficult and challenging task and usually requires highly specific and costly instruments. Yet, the stereoisomerism of contaminants is presently not considered in detail. For example, ~25% of all pesticides produced are chiral compounds and in many cases they are used as racemic mixtures, while about 70–80% of medical drugs are enantiopure molecules. In this context, the development of portable chemical sensors devices which are reliable, sensitive and rapid, capable of fast, simple and real-time in situ and on site analysis for sensing and discrimination of chiral molecules presents an attractive breakthrough target compared to existing standard instrumental methods.
Therefore, the aim of this Special Issue is to highlight and overview all aspects of chiral pollution on environment and corresponding detection by using modern analytical approaches.

This issue will also include the design and fabrication of organic/inorganic as well as hybrid sensitive materials. Different aspects will be covered ranging, for example, from the synthesis of the proper building blocks and their characterization to their eventual deposition in solid-state.

All types of papers, including comprehensive reviews on general environmental issues, full experimental or theoretical papers, comments, and others are welcome for consideration.

Prof. Dr. Victor Borovkov
Prof. Riina Aav
Prof. Roberto Paolesse
Dr. Manuela Stefanelli
Dr. Donato Monti

Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Chemosensors is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1600 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • chiral pollutants
  • environment
  • chirality
  • stereoisomerism
  • enantiomers
  • chirality sensors
  • self-assembly
  • supramolecular systems

Published Papers (4 papers)

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Research

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Article
2,12-Diaza[6]helicene: An Efficient Non-Conventional Stereogenic Scaffold for Enantioselective Electrochemical Interphases
Chemosensors 2021, 9(8), 216; https://doi.org/10.3390/chemosensors9080216 - 10 Aug 2021
Viewed by 452
Abstract
The new configurationally stable, unsymmetrical 2,12-diaza[6]helicene was synthesized as a racemate and the enantiomers were separated in an enantiopure state by semi-preparative HPLC on chiral stationary phase. Under selected alkylation conditions it was possible to obtain both the enantiopure 2-N-mono- and [...] Read more.
The new configurationally stable, unsymmetrical 2,12-diaza[6]helicene was synthesized as a racemate and the enantiomers were separated in an enantiopure state by semi-preparative HPLC on chiral stationary phase. Under selected alkylation conditions it was possible to obtain both the enantiopure 2-N-mono- and di-N-ethyl quaternary iodides. Metathesis with bis(trifluoromethanesulfonyl)imide anion gave low-melting salts which were tested as inherently chiral additives to achiral ionic liquids for the electrochemical enantiodiscrimination of chiral organic probes in voltammetric experiments. Remarkable differences in the oxidation potentials of the enantiomers of two probes, a chiral ferrocenyl amine and an aminoacid, were achieved; the differences increase with increasing additive concentration and number of alkylated nitrogen atoms. Full article
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Article
Absolute Configuration Sensing of Chiral Aryl- and Aryloxy-Propionic Acids by Biphenyl Chiroptical Probes
Chemosensors 2021, 9(7), 154; https://doi.org/10.3390/chemosensors9070154 - 24 Jun 2021
Cited by 1 | Viewed by 341
Abstract
The absolute configuration of chiral 2-aryl and 2-aryloxy propionic acids, which are among the most common chiral environmental pollutants, has been readily and reliably established by either electronic circular dichroism spectroscopy or optical rotation measurements employing suitably designed 4,4′-disubstituted biphenyl probes. In fact, [...] Read more.
The absolute configuration of chiral 2-aryl and 2-aryloxy propionic acids, which are among the most common chiral environmental pollutants, has been readily and reliably established by either electronic circular dichroism spectroscopy or optical rotation measurements employing suitably designed 4,4′-disubstituted biphenyl probes. In fact, the 4,4′-biphenyl substitution gives rise to a red shift of the diagnostic electronic circular dichroism signal of the biphenyl A band employed for the configuration assignment, removing its overlap with other interfering dichroic bands and allowing its clear sign identification. The largest A band red shift, and thus the most reliable results, are obtained by employing as a probe the 4,4′-dinitro substituted biphenylazepine 3c. The method was applied to the absolute configuration assignment of 2-arylpropionic acids ibuprofen (1a), naproxen (1b), ketoprofen (1c) and flurbiprofen (1d), as well as to the 2-aryloxypropionic acids 2-phenoxypropionic acid (2a) and 2-naphthoxypropionic acid (2b). This approach, allowing us to reveal the sample’s absolute configuration by simple optical rotation measurements, is potentially applicable to online analyses of both the enantiomeric composition and absolute configuration of these chiral pollutants. Full article
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Review

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Review
Estimation of Enantiomeric Excess Based on Rapid Host–Guest Exchange
Chemosensors 2021, 9(9), 259; https://doi.org/10.3390/chemosensors9090259 - 09 Sep 2021
Viewed by 288
Abstract
Chiral molecules possess enantiomers that have non-superimposable chemical structures but exhibit identical nuclear magnetic resonance (NMR) spectra. This feature prevents the use of NMR spectroscopic methods for the determination of enantiomeric excesses (ee) of chiral molecules, using simple mixtures of their [...] Read more.
Chiral molecules possess enantiomers that have non-superimposable chemical structures but exhibit identical nuclear magnetic resonance (NMR) spectra. This feature prevents the use of NMR spectroscopic methods for the determination of enantiomeric excesses (ee) of chiral molecules, using simple mixtures of their enantiomers. Recently, however, it was reported that the addition of a symmetrical prochiral molecule (a reporter or host) into a solution of chiral analyte can lead to estimation of ee through interactions involving rapid exchange of the chiral analyte (guest) in the formed host–guest complex. This is due to the ee-dependent splitting of NMR resonances of the prochiral host molecule based on averaging the chemical shift non-equivalency caused by the presence of a chiral guest. The mechanism is not dependent on diastereomer formation, and 1:1 host–guest complexes can also show ee-dependent NMR peak splitting. Prochiral molecules capable of ee sensing using the NMR technique are now referred to as so-called prochiral solvating agents (pro-CSAs). pro-CSAs represent a family of reagents distinct from the commonly used NMR chiral derivatizing reagents (where chiral auxiliaries are used to derivatize enantiomers to diastereomers) or chiral solvating agents (where chiral auxiliaries interact in an asymmetric manner with analyte enantiomers). pro-CSA methods are unique since neither pro-CSA nor NMR contains chiral factors, making the technique neutral with respect to chirality. Here, we review our recent work on this matter involving several different nominally achiral receptor molecules whose unique guest binding properties and solution characteristics (especially with regard to NMR spectroscopy) allow for the estimation of ee in the corresponding chiral guests. Full article
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Review
Recognition and Sensing of Chiral Organic Molecules by Chiral Porphyrinoids: A Review
Chemosensors 2021, 9(8), 204; https://doi.org/10.3390/chemosensors9080204 - 03 Aug 2021
Viewed by 490
Abstract
Porphyrinoids are extremely attractive for their electronic, optical, and coordination properties as well as for their versatile substitution at meso/β-positions. All these features allow porphyrinoids to behave as chiroptical hosts for chiral recognition by means of non-covalent interactions towards chiral guests. Over the [...] Read more.
Porphyrinoids are extremely attractive for their electronic, optical, and coordination properties as well as for their versatile substitution at meso/β-positions. All these features allow porphyrinoids to behave as chiroptical hosts for chiral recognition by means of non-covalent interactions towards chiral guests. Over the years, chiral discrimination of chiral molecules such as amino acids, alcohols, amines, hydroxy-carboxylic acids, etc. has aroused the interest of the scientific community. Hence, this review aims to report on the progress to date by illustrating some relevant research regarding the chiral recognition of a multitude of chiral organic guests through several chiral mono- and bis-porphyrins via different spectroscopic techniques. Full article
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