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Highly Stable Copper Nanoparticles Linked to Organic Frameworks as Recyclable Catalyst for Three‐Component Click Cycloaddition in Water
Author(s) -
Prakash Sadasivan P.,
Gopidas Karical R.
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601127
Subject(s) - catalysis , tetrafluoroborate , alkyne , biphenylene , nanoparticle , sodium borohydride , click chemistry , copper , chemistry , cycloaddition , azide , polymer chemistry , combinatorial chemistry , inorganic chemistry , materials science , organic chemistry , nanotechnology , ionic liquid , polymer , phenylene
Synthesis, characterization and catalytic applications of highly stable copper‐nanoparticles linked to aromatic frameworks are reported. Synthesis of these nanoparticles was achieved in a one‐pot reaction which involved the simultaneous reduction of CuCl 2 .2H 2 O and 4,4’‐biphenylene‐bis‐diazonium tetrafluoroborate using sodium borohydride. Copper atoms formed upon reduction of Cu ions undergo clustering, leading to the formation of copper nanoparticles. At the same time, 4,4’‐biphenylene‐bis‐diazonium tetrafluoroborate are converted to biphenylene biradicals, which undergoes rapid addition reactions with each other and also on to the nanoparticle surfaces resulting in the formation of aromatic framework linked Cu nanoparticles. Four different types of nanoparticles were prepared by varying the concentration of the metal salts and the ligands. The structure and morphology of these materials were studied using XRD, XPS, SEM and HRTEM analysis. The materials were found to be very good catalysts for click reactions between azides and alkynes and exhibited TOF values as high as 305400 h −1 . They also efficiently catalyzed the one‐pot click reactions involving azide precursors, sodium azide and alkyne. TOF up to 99000 h −1 were observed for these reactions.