Jump to main content
Jump to site search


Hydrosoluble Cu(I)-DAPTA complexes: synthesis, characterization, luminescence thermochromism and catalytic activity for microwave-assisted three-component azide–alkyne cycloaddition click reaction

Author affiliations

Abstract

New hydrosoluble and air-stable Cu(I) halide compounds, viz. [CuX(DAPTA)3] (1) and (2), and [Cu(μ-X)(DAPTA)2]2 (3) and (4) (X = Br or I, in this order), have been prepared by reacting Cu(I) halide (i.e., bromide or iodide) with 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) under mild conditions. They represent the first examples of Cu(I) halide complexes bearing the DAPTA ligand, which have been fully characterized by elemental analysis, IR, 1H, 13C{1H} and 31P{1H} NMR spectroscopies, ESI-MS+ and, for 4, also by single-crystal X-ray diffraction (SCXRD) analyses. Complexes 1–4 are efficient catalysts for the one-pot microwave assisted three-component (terminal alkyne, organic halide and NaN3) Huisgen cycloaddition reaction in aqueous media to afford the corresponding disubstituted triazoles. The catalysis proceeds with a broad alkyne substrate scope and according to “click rules”. Photophysical studies of compound 4 showed an unusual reversible thermochromic behaviour exhibiting a blue emission at 298 K due to the halide-to-ligand charge transfer (3XLCT) and a red emission at 77 K because of the {Cu2I2} unit.

Graphical abstract: Hydrosoluble Cu(i)-DAPTA complexes: synthesis, characterization, luminescence thermochromism and catalytic activity for microwave-assisted three-component azide–alkyne cycloaddition click reaction

Back to tab navigation

Supplementary files

Publication details

The article was received on 29 Mar 2018, accepted on 27 Apr 2018 and first published on 16 May 2018


Article type: Paper
DOI: 10.1039/C8DT01232F
Citation: Dalton Trans., 2018, Advance Article
  •   Request permissions

    Hydrosoluble Cu(I)-DAPTA complexes: synthesis, characterization, luminescence thermochromism and catalytic activity for microwave-assisted three-component azide–alkyne cycloaddition click reaction

    A. G. Mahmoud, M. F. C. Guedes da Silva, J. Sokolnicki, P. Smoleński and A. J. L. Pombeiro, Dalton Trans., 2018, Advance Article , DOI: 10.1039/C8DT01232F

Search articles by author

Spotlight

Advertisements