The Impact of Copper‐Catalyzed Alkyne–Azide 1,3‐Dipolar Cycloaddition in Fullerene Chemistry

Abstract

Click reactions largely cross the borders of organic synthetic chemistry and are now at the forefront of many interdisciplinary studies at the interfaces between chemistry, physics, and biology. As part of this research, our group is involved in a program on the development of clickable fullerene building blocks and their application in the preparation of a large variety of new advanced materials and bioactive compounds. Importantly, the introduction of the click chemistry concept in fullerene chemistry allowed us to produce compounds that would barely be accessible by using the classical tools of fullerene chemistry. This is particularly the case for the conjugation of fullerenes with other carbon nanoforms, such as carbon nanohorns and graphene. It is also the case for most of the sophisticated molecular ensembles constructed from clickable fullerene hexa-adduct building blocks. In this paper, we have summarized our ongoing progress in this particular field.

Pillar[5]arene‐Based Glycoclusters: Synthesis and Multivalent Binding to Pathogenic Bacterial Lectins

“…The most convenient method for the conjugation of two molecular entities is probably the Cu I ‐assisted azide–alkyne cycloaddition (CuAAC) . The high yields obtained in such 1,3‐dipolar cycloadditions are particularly relevant when a high number of reactions must be performed at once on a single molecular scaffold.…”

Antiviral activity of self-assembled glycodendro[60]fullerene monoadducts

“…1) we have employed an efficient click chemistry strategy. 19,20 Thus, we have carried out the Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction (CuAAC) 21 between the fullerene properly modified with terminal alkyne moieties 16 and mannose or galactose glycodendrons endowed with an azide group in their focal position. 22 The CuAAC reaction was carried out in the presence of metallic copper, CuBr•SMe 2 as source of Cu (I) and DMSO as solvent, following the optimized methodology previously reported.…”

Biologically Active Heteroglycoclusters Constructed on a Pillar[5]arene‐Containing [2]Rotaxane Scaffold

“…For the synthetic chemist, the challenge is often to increase the complexity of the molecular structures without being limited by the synthetic route. In this respect, the use of pre‐constructed nanoscaffolds allowing the successive grafting of different molecular entities through the use of efficient orthogonal synthetic strategies is very attractive 1. Functionalizable scaffolds have been particularly useful for the efficient preparation of new materials for various applications, including liquid–crystalline materials2 or photo‐ and electro‐active molecular devices 3.…”