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Special Issue "Click Chemistry"

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

Deadline for manuscript submissions: closed (31 July 2010)

Special Issue Editor

Guest Editor
Prof. Dr. Christian Girard (Website)

Unité de Technologies Chimiques & Biologiques pour la Santé, Equipe SEISAD - Synthèse Electrochimie, Imagerie et Systèmes Analytiques pour le Diagnostique, UMR 8258 CNRS / U 1022 INSERM, Ecole Nationale Supérieure de Chimie de Paris 11, rue P. & M. Curie, 75231 Paris cedex 05, France
Fax: +33-1 44 27 64 96

Special Issue Information

Dear Colleagues,

Click-chemistry is a new way of thinking molecular construction that emerges at the turn of this century. This concept, introduced by K. B. Sharpless, is based on the use of fast and efficient reactions between building blocks that opens the way to quasi-illimited variations in chemical architecture. Click-chemistry permits the construction of highly diversified structures through the use of reactive subunits, that can be joined using nucleophilic and electrophilic substitutions, ring opening reactions, cycloadditions reactions such as the copper (I)-modified Huisgen reaction and the Diels-Alder one, additions to unsaturated bonds, carbonyl chemistry, and so on. The scope of this new way of thinking molecular construction is large and has found many applications in classical organic synthesis, polymers and material sciences, as well as at the biological interface, with biocompatible conditions.

This Special Issue of Molecules has the objective to present articles that cover the use of click-chemistry to generate molecular diversity by organic synthesis (molecular libraries, chemical architecture, complexe structures, etc.), as well as its application at the frontier with other sciences.

Prof. Dr. Christian Girard
Guest Editor

Keywords

  • click-chemistry
  • organic synthesis
  • molecular diversity
  • methodology
  • application
  • interfaces with other sciences (pharmaceutical, biological, polymers, materials, etc.)

Published Papers (4 papers)

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Research

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Open AccessArticle Automated Synthesis of a 96 Product-Sized Library of Triazole Derivatives Using a Solid Phase Supported Copper Catalyst
Molecules 2010, 15(5), 3087-3120; doi:10.3390/molecules15053087
Received: 29 March 2010 / Revised: 20 April 2010 / Accepted: 26 April 2010 / Published: 28 April 2010
Cited by 18 | PDF Full-text (596 KB)
Abstract
This article deal with the parallel synthesis of a 96 product-sized library using a polymer-based copper catalyst that we developed which can be easily separated from the products by simple filtration. This gave us the opportunity to use this catalyst in an [...] Read more.
This article deal with the parallel synthesis of a 96 product-sized library using a polymer-based copper catalyst that we developed which can be easily separated from the products by simple filtration. This gave us the opportunity to use this catalyst in an automated chemical synthesis station (Chemspeed ASW-2000). Studies and results about the preparation of the catalyst, its use in different solvent systems, its recycling capabilities and its scope and limitations in the synthesis of this library will be addressed. The synthesis of the triazole library and the very good results obtained will finally be discussed. Full article
(This article belongs to the Special Issue Click Chemistry)
Open AccessArticle Cationic Heteroleptic Cyclometalated IridiumIII Complexes Containing Phenyl-Triazole and Triazole-Pyridine Clicked Ligands
Molecules 2010, 15(3), 2039-2059; doi:10.3390/molecules15032039
Received: 8 February 2010 / Revised: 8 March 2010 / Accepted: 18 March 2010 / Published: 23 March 2010
Cited by 42 | PDF Full-text (815 KB) | Supplementary Files
Abstract
Novel heteroleptic iridium complexes containing the 1-substituted-4-phenyl-1H-1,2,3-triazole (phtl) cyclometalating ligand have been synthesized. The 3+2 Huisgen dipolar cycloaddition method (‘click’ chemistry) was utilized to prepare a class of bidentate ligands (phtl) bearing different substituents on the triazole moiety. By using [...] Read more.
Novel heteroleptic iridium complexes containing the 1-substituted-4-phenyl-1H-1,2,3-triazole (phtl) cyclometalating ligand have been synthesized. The 3+2 Huisgen dipolar cycloaddition method (‘click’ chemistry) was utilized to prepare a class of bidentate ligands (phtl) bearing different substituents on the triazole moiety. By using various ligands (phtl-R1 and pytl-R2) (R1=adamantane, methyl and R2=adamantane, methyl, β-cyclodextrin, ursodeoxycholic acid), we prepared a small library of new luminescent ionic iridium complexes [Ir(phtr-R1)2(pytl-R2)]Cl and report on their photophysical properties. The flexibility of the clicking approach allows a straightforward control on the chemical-physical properties of the complexes by varying the nature of the substituent on the ligand. Full article
(This article belongs to the Special Issue Click Chemistry)

Review

Jump to: Research

Open AccessReview Click Reactions and Boronic Acids: Applications, Issues, and Potential Solutions
Molecules 2010, 15(8), 5768-5781; doi:10.3390/molecules15085768
Received: 30 June 2010 / Revised: 27 July 2010 / Accepted: 4 August 2010 / Published: 23 August 2010
Cited by 19 | PDF Full-text (156 KB)
Abstract
Boronic acids have been widely used in a wide range of organic reactions, in the preparation of sensors for carbohydrates, and as potential pharmaceutical agents. With the growing importance of click reactions, inevitably they are also applied to the synthesis of compounds [...] Read more.
Boronic acids have been widely used in a wide range of organic reactions, in the preparation of sensors for carbohydrates, and as potential pharmaceutical agents. With the growing importance of click reactions, inevitably they are also applied to the synthesis of compounds containing the boronic acid moiety. However, such applications have unique problems. Chief among them is the issue of copper-mediated boronic acid degradation in copper-assisted [2,3]-cycloadditions involving an alkyne and an azido compound as the starting materials. This review summarizes recent developments, analyzes potential issues, and discusses known as well as possible solutions. Full article
(This article belongs to the Special Issue Click Chemistry)
Open AccessReview Click Chemistry for the Synthesis of RGD-Containing Integrin Ligands
Molecules 2010, 15(1), 178-197; doi:10.3390/molecules15010178
Received: 1 December 2009 / Revised: 19 December 2009 / Accepted: 31 December 2009 / Published: 6 January 2010
Cited by 21 | PDF Full-text (161 KB)
Abstract
In the last few years click chemistry reactions, and in particular coppercatalyzed cycloadditions, have been used intensively for the preparation of new bioconjugate molecules and materials applicable to biomedical and pharmaceutical areas. This review will be focused on conjugates of the tripeptide [...] Read more.
In the last few years click chemistry reactions, and in particular coppercatalyzed cycloadditions, have been used intensively for the preparation of new bioconjugate molecules and materials applicable to biomedical and pharmaceutical areas. This review will be focused on conjugates of the tripeptide Arg-Gly-Asp formed by means of click chemistry reactions. This sequence is a well known binding motif for specific transmembrane proteins and is involved in cellular adhesion to the extracellular matrix, allowing the selective recognition of the biomolecule or polymer in which it is incorporated. Full article
(This article belongs to the Special Issue Click Chemistry)

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