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Organic Azides 2019
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Organic Azides 2019

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

Deadline for manuscript submissions: closed (31 December 2019) | Viewed by 27914

Special Issue Editor

Prof. Dr. Klaus Banert

E-Mail Website
Guest Editor
Technische Universität Chemnitz, Organische Chemie, Strasse der Nationen 62, 09111 Chemnitz, Germany
Interests: synthetic methods; reaction mechanisms; short-lived species; structure assignments; organic azides; heterocycles; cycloaddition reactions
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The azido unit belongs to the most important functional groups in organic chemistry because it is a highly useful device to prepare a variety of nitrogen-containing products such as amines and amine derivatives, nitren-derived compounds, nitrogen heterocycles, and many others. Since the discovery of the first organic azide by Peter Griess in 1864, a large number of applications in organic synthesis as well as life sciences and material sciences emphasize the significance of organic azides.

In recent years, however, the progress of azide chemistry has become very rapid due to several new transformations based on radical and oxidation reactions, especially owing to the introduction of click chemistry, including the 1,3-dipolar cycloaddition of azides at alkynes. Moreover, molecules with novel combinations of the azido unit and adjacent other functional groups, as well as new applications of organic azides as high-energy materials and in biochemically relevant ligation and labeling methods, have increased the general interest in azido compounds.

In this Special Issue of Molecules, research articles covering all areas of organic azide chemistry are welcome to present the state of research in connection with this exciting functional group.

Prof. Dr. Klaus Banert
Guest Editor

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 submissions that pass pre-check are 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. Molecules is an international peer-reviewed open access semimonthly 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 2700 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

  • New methods to prepare organic azides
  • Novel types of organic azides
  • New reactions of organic azides
  • Application in bioorganic chemistry
  • Application in material sciences.

Published Papers (5 papers)

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Research

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20 pages, 5339 KiB  
Article
Synthesis and Spectral Study of a New Family of 2,5-Diaryltriazoles Having Restricted Rotation of the 5-Aryl Substituent
by Biligma Tsyrenova and Valentine Nenajdenko
Molecules 2020, 25(3), 480; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25030480 - 23 Jan 2020
Cited by 19 | Viewed by 2668
Abstract
Efficient synthesis of 2,5-diaryl substituted 4-azido-1,2,3-triazoles by the reaction of sodium azide with dichlorosubstituted diazadienes was demonstrated. The optical properties of the prepared azidotriazoles were studied to reveal a luminescence maximum in the 360–420 nm region. To improve the luminescence quantum yields a [...] Read more.
Efficient synthesis of 2,5-diaryl substituted 4-azido-1,2,3-triazoles by the reaction of sodium azide with dichlorosubstituted diazadienes was demonstrated. The optical properties of the prepared azidotriazoles were studied to reveal a luminescence maximum in the 360–420 nm region. To improve the luminescence quantum yields a family of 4-azido-1,2,3-triazoles bearing ortho-propargyloxy substituents in the 5 position was prepared. Subsequent intramolecular thermal cyclization permits to construct additional triazole fragment and obtain unique benzoxazocine derivatives condensed with two triazole rings. This new family of condensed heterocycles has a flattened heterocyclic system structure to provide more conjugation of the 5-aryl fragment with the triazole core. As a result, a new type of UV/“blue light-emitting” materials with better photophysical properties was obtained. Full article
(This article belongs to the Special Issue Organic Azides 2019)
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16 pages, 3119 KiB  
Article
Synthesis of Chromium(II) Complexes with Chelating Bis(alkoxide) Ligand and Their Reactions with Organoazides and Diazoalkanes
by Sudheer S. Kurup, Richard J. Staples, Richard L. Lord and Stanislav Groysman
Molecules 2020, 25(2), 273; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25020273 - 09 Jan 2020
Cited by 7 | Viewed by 4226
Abstract
Synthesis of new chromium(II) complexes with chelating bis(alkoxide) ligand [OO]Ph (H2[OO]Ph = [1,1′:4′,1′’-terphenyl]-2,2′’-diylbis(diphenylmethanol)) and their subsequent reactivity in the context of catalytic production of carbodiimides from azides and isocyanides are described. Two different Cr(II) complexes are obtained, as a [...] Read more.
Synthesis of new chromium(II) complexes with chelating bis(alkoxide) ligand [OO]Ph (H2[OO]Ph = [1,1′:4′,1′’-terphenyl]-2,2′’-diylbis(diphenylmethanol)) and their subsequent reactivity in the context of catalytic production of carbodiimides from azides and isocyanides are described. Two different Cr(II) complexes are obtained, as a function of the crystallization solvent: mononuclear Cr[OO]Ph(THF)2 (in toluene/THF, THF = tetrahydrofuran) and dinuclear Cr2([OO]Ph)2 (in CH2Cl2/THF). The electronic structure and bonding in Cr[OO]Ph(THF)2 were probed by density functional theory calculations. Isolated Cr2([OO]Ph)2 undergoes facile reaction with 4-MeC6H4N3, 4-MeOC6H4N3, or 3,5-Me2C6H3N3 to yield diamagnetic Cr(VI) bis(imido) complexes; a structure of Cr[OO]Ph(N(4-MeC6H4))2 was confirmed by X-ray crystallography. The reaction of Cr2([OO]Ph)2 with bulkier azides N3R (MesN3, AdN3) forms paramagnetic products, formulated as Cr[OO]Ph(NR). The attempted formation of a Cr–alkylidene complex (using N2CPh2) instead forms chromium(VI) bis(diphenylmethylenehydrazido) complex Cr[OO]Ph(NNCPh2)2. Catalytic formation of carbodiimides was investigated for the azide/isocyanide mixtures containing various aryl azides and isocyanides. The formation of carbodiimides was found to depend on the nature of organoazide: whereas bulky mesitylazide led to the formation of carbodiimides with all isocyanides, no carbodiimide formation was observed for 3,5-dimethylphenylazide or 4-methylphenylazide. Treatment of Cr2([OO]Ph)2 or H2[OO]Ph with NO+ leads to the formation of [1,2-b]-dihydroindenofluorene, likely obtained via carbocation-mediated cyclization of the ligand. Full article
(This article belongs to the Special Issue Organic Azides 2019)
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Review

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28 pages, 5732 KiB  
Review
Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 2—Azides, Phthalocyanines, Subphthalocyanines and Porphyrazines
by Ana R. L. Araújo, Augusto C. Tomé, Carla I. M. Santos, Maria A. F. Faustino, Maria G. P. M. S. Neves, Mário M. Q. Simões, Nuno M. M. Moura, Sultan T. Abu-Orabi and José A. S. Cavaleiro
Molecules 2020, 25(7), 1745; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25071745 - 10 Apr 2020
Cited by 8 | Viewed by 3954
Abstract
The reaction between organic azides and alkyne derivatives via the Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) is an efficient strategy to combine phthalocyanines and analogues with different materials. As examples of such materials, it can be considered the following ones: graphene oxide, carbon nanotubes, silica [...] Read more.
The reaction between organic azides and alkyne derivatives via the Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) is an efficient strategy to combine phthalocyanines and analogues with different materials. As examples of such materials, it can be considered the following ones: graphene oxide, carbon nanotubes, silica nanoparticles, gold nanoparticles, and quantum dots. This approach is also being relevant to conjugate phthalocyanines with carbohydrates and to obtain new sophisticated molecules; in such way, new systems with significant potential applications become available. This review highlights recent developments on the synthesis of phthalocyanine, subphthalocyanine, and porphyrazine derivatives where CuAAC reactions are the key synthetic step. Full article
(This article belongs to the Special Issue Organic Azides 2019)
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63 pages, 33757 KiB  
Review
Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles
by Ana R. L. Araújo, Augusto C. Tomé, Carla I. M. Santos, Maria A. F. Faustino, Maria G. P. M. S. Neves, Mário M. Q. Simões, Nuno M. M. Moura, Sultan T. Abu-Orabi and José A. S. Cavaleiro
Molecules 2020, 25(7), 1662; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25071662 - 03 Apr 2020
Cited by 11 | Viewed by 5447
Abstract
Azides and porphyrinoids (such as porphyrin and corrole macrocycles) can give rise to new derivatives with significant biological properties and as new materials’ components. Significant synthetic approaches have been studied. A wide range of products (e.g., microporous organic networks, rotaxane and dendritic motifs, [...] Read more.
Azides and porphyrinoids (such as porphyrin and corrole macrocycles) can give rise to new derivatives with significant biological properties and as new materials’ components. Significant synthetic approaches have been studied. A wide range of products (e.g., microporous organic networks, rotaxane and dendritic motifs, dendrimers as liquid crystals, as blood substitutes for transfusions and many others) can now be available and used for several medicinal and industrial purposes. Full article
(This article belongs to the Special Issue Organic Azides 2019)
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29 pages, 5236 KiB  
Review
Reactive & Efficient: Organic Azides as Cross-Linkers in Material Sciences
by Marvin Schock and Stefan Bräse
Molecules 2020, 25(4), 1009; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25041009 - 24 Feb 2020
Cited by 43 | Viewed by 11037
Abstract
The exceptional reactivity of the azide group makes organic azides a highly versatile family of compounds in chemistry and the material sciences. One of the most prominent reactions employing organic azides is the regioselective copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition with alkynes yielding 1,2,3-triazoles. Other [...] Read more.
The exceptional reactivity of the azide group makes organic azides a highly versatile family of compounds in chemistry and the material sciences. One of the most prominent reactions employing organic azides is the regioselective copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition with alkynes yielding 1,2,3-triazoles. Other named reactions include the Staudinger reduction, the aza-Wittig reaction, and the Curtius rearrangement. The popularity of organic azides in material sciences is mostly based on their propensity to release nitrogen by thermal activation or photolysis. On the one hand, this scission reaction is accompanied with a considerable output of energy, making them interesting as highly energetic materials. On the other hand, it produces highly reactive nitrenes that show extraordinary efficiency in polymer crosslinking, a process used to alter the physical properties of polymers and to boost efficiencies of polymer-based devices such as membrane fuel cells, organic solar cells (OSCs), light-emitting diodes (LEDs), and organic field-effect transistors (OFETs). Thermosets are also suitable application areas. In most cases, organic azides with multiple azide functions are employed which can either be small molecules or oligo- and polymers. This review focuses on nitrene-based applications of multivalent organic azides in the material and life sciences. Full article
(This article belongs to the Special Issue Organic Azides 2019)
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