Copper-free cycloaddition of azide and alkyne in crystalline state facilitated by arene–perfluoroarene interactions

Abstract

Facilitated by arene-perfluoroarene interactions, a 1,3-dipolar cycloaddition between azide and alkyne proceeded in the crystals at room temperature in the absence of a copper(I) catalyst, and the reaction was confirmed to be a highly regioselective process giving the 1,4-triazole product.

Luminescence Enhancement by p‐Substituent Variation

“…Compounds with this type of π–π interaction – azido interactions – have previously been published in the literature, though rarely, but never discussed . For instance, for the layered zinc complex, which was published, we found the layers to be linked by similar azido contacts [ d (N ··· N) = 2.988 and 3.053 Å]; however, only the zinc coordination environment was discussed by the authors, as this complex was used as a reagent in the Huisgen reaction.…”

Efficient and Regioselectivity‐Tunable Metal‐Free Polycycloaddition of Activated Azide and Alkynes

“…However, the metallic residues are toxic and destructive if the products are going to be used in biological and optoelectronic fields . In this context, the development of metal‐free click polymerization (MFCP) is particularly necessary …”

Self-assembly of diphenylalanine with preclick components as capping groups

“…The cycles stack in sheets forming hydrophobic tubes that, in turn, self-associate forming fibres. For Poc-FF-N 3 fibres we hypothesize the formation of alkyne···azide interactions, which have been observed in both aromatic organic compounds and biomolecules blocked with azide and alkyl groups, [56][57][58][59] and the the participation of stronger intermolecular interactions involving the peptide and/or phenyl groups. The structure of both the sheets and the tubes has been examined in the next sub-section.…”

“…azide-alkyne cycloaddition) for the synthesis of molecules with different architectures and functional groups, [37][38][39] were chosen as terminal protecting groups. When they are in close proximity, the azide and alkyne motifs have been proved to interact through attractive non-covalent forces, [40][41][42][43] even though the resulting dipole- and - interactions are apparently weaker than the - stacking typically found for aromatic rings. Thus, the crystal structure of compounds formed by arene rings with azide and alkyne functional groups positioned at opposite ends was found to be predominantly determined by face-to-face stacking motif of the rings.…”

“…Thus, the crystal structure of compounds formed by arene rings with azide and alkyne functional groups positioned at opposite ends was found to be predominantly determined by face-to-face stacking motif of the rings. 42,43 On the other hand, Reches and coworkers 44 recently reported a series of FF-derivatives with free ends in which the azide group was introduced as a substituent in the side phenyl ring of one or the two F residues. Interestingly, the peptide substituted at the side group of the two F residues self-assembled into ordered spherical and porous structures in pure water and 1:1 methanol (MeOH) : water, whereas peptides with a single substitution did not form such ordered structures.…”