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

Dalton Transactions : an International Journal of Inorganic Chemistry
Abdallah G MahmoudArmando J L Pombeiro

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.

References

Feb 19, 2002·Chemical Reviews·Peter C. FordJames Bourassa
Dec 18, 2003·Drug Discovery Today·Hartmuth C Kolb, K Barry Sharpless
Jan 6, 2005·Journal of the American Chemical Society·Fahmi HimoValery V Fokin
Aug 16, 2005·Angewandte Chemie·Stefan BräseViktor Zimmermann
Dec 21, 2005·Chemical Society Reviews·Chao-Jun Li, Liang Chen
Sep 14, 2006·Chemistry : a European Journal·Silvia Díez-GonzálezSteven P Nolan
Feb 20, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·Lei YangRobert P Houser
Jul 11, 2007·Chemical Society Reviews·John E Moses, Adam D Moorhouse
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
May 16, 2008·Chemical Communications : Chem Comm·Nicolas CandelonJean-Marc Vincent
May 24, 2008·Chemical Society Reviews·C Oliver Kappe
Jun 21, 2008·Chemistry : a European Journal·Victorio CadiernoJosé Gimeno
Oct 3, 2008·Chemical Communications : Chem Comm·Silvia Díez-GonzálezSteven P Nolan
Dec 22, 2010·Journal of the American Chemical Society·Israel CanoPedro J Pérez
Mar 10, 2011·The Journal of Organic Chemistry·Steven Lal, Silvia Díez-González
May 19, 2011·Macromolecular Rapid Communications·Pierre D Harvey, Michael Knorr
Aug 5, 2011·Inorganic Chemistry·Rafał CzerwieniecHartmut Yersin
Oct 1, 2011·Inorganic Chemistry·Sandrine PerruchasJean-Pierre Boilot
Aug 24, 2013·The Journal of Physical Chemistry. a·Markus J LeitlHartmut Yersin
Apr 25, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Ashok YadavRamamoorthy Boomishankar
Apr 11, 2015·Inorganic Chemistry·Quentin BenitoSandrine Perruchas
Jul 21, 2015·Metallomics : Integrated Biometal Science·V GandinC Marzano
Aug 19, 2015·Organic & Biomolecular Chemistry·Estela HaldónPedro J Pérez
Oct 27, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·F FarinellaD Braga
Dec 9, 2017·Chemical Reviews·Taku KitanosonoShu Kobayashi

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Citations

Jan 15, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Abdallah G MahmoudArmando J L Pombeiro
Sep 29, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Jian-Fang LiJian-Fang Ma
Nov 27, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Abdallah G MahmoudArmando J L Pombeiro
Mar 9, 2021·Advanced Synthesis & Catalysis·Thomas Schlatzer, Rolf Breinbauer
May 11, 2021·Beilstein Journal of Organic Chemistry·Shivani GulatiNagula Shankaraiah
May 12, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Abdallah G MahmoudArmando J L Pombeiro

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Methods Mentioned

BETA
acetylation
NMR
X-ray

Software Mentioned

WinGX System
SIR97
Bruker SMART
Bruker SAINT
SHELXL

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