A dynamic tricopper double helicate

Chemistry : a European Journal
Marie HutinJonathan R Nitschke

Abstract

The reaction between 8-aminoquinoline, 1,10-phenantholine-2,9-dicarbaldehyde, and copper(I) tetrafluoroborate gave a quantitative yield of a tricopper double helicate. The presence of dynamic covalent imine (C=N) bonds allowed this assembly to participate in two reactions not previously known in helicate chemistry: 1) It could be prepared through subcomponent substitution from a dicopper double helicate that contained aniline residues. An electron-poor aniline was quantitatively displaced; a more electron-rich aniline competed effectively with the aminoquinoline, setting up an equilibrium between dicopper and tricopper helicates that could be displaced towards the tricopper through the addition of further copper(I). 2) Both dicopper and tricopper helicates could be prepared simultaneously from a mixture of phenanthroline dialdehyde, aniline, and aminoquinoline, which contained all possible imine condensation products in equilibrium. Following the addition of copper(I), thermodynamic equilibration on both covalent and coordinative levels eliminated all partially-formed and mixed imine ligands from the mixture, leaving the helicates as exclusive products.

References

Mar 18, 1997·Proceedings of the National Academy of Sciences of the United States of America·I Huc, J M Lehn
Mar 28, 2001·Science·J M Lehn, A V Eliseev
Jun 20, 2001·Accounts of Chemical Research·J F Stoddart
Jun 15, 1993·Proceedings of the National Academy of Sciences of the United States of America·R KramerA Marquis-Rigault
Feb 14, 2002·Journal of the American Chemical Society·Johannes A A W ElemansRoeland J M Nolte
Feb 19, 2002·Chemical Reviews·Claude PiguetGérard Hopfgartner
Mar 7, 2002·Proceedings of the National Academy of Sciences of the United States of America·Charles Michael DrainHeather Sommers
Apr 4, 2002·Proceedings of the National Academy of Sciences of the United States of America·Jean-Marie Lehn
Apr 18, 2002·Proceedings of the National Academy of Sciences of the United States of America·Yasuo KubotaMakoto Fujita
Nov 20, 2002·Accounts of Chemical Research·S Russell Seidel, Peter J Stang
Dec 10, 2002·Current Opinion in Chemical Biology·Wei Yin SunMakoto Fujita
Dec 20, 2002·Angewandte Chemie·Stuart J RowanJ Fraser Stoddart
Aug 22, 2003·Nature·Pall ThordarsonRoeland J M Nolte
Oct 1, 2003·Proceedings of the National Academy of Sciences of the United States of America·Jonathan R Nitschke, Jean-Marie Lehn
Mar 20, 2004·Science·Jovica D BadjicJ Fraser Stoddart
May 29, 2004·Science·Kelly S ChichakJ Fraser Stoddart
Jul 13, 2004·Angewandte Chemie·George M Whitesides
Sep 17, 2004·Chemistry : a European Journal·Christoph A SchalleyFritz Vögtle
Oct 7, 2004·Chemical Communications : Chem Comm·Olli Ikkala, Gerrit ten Brinke
Nov 30, 2004·Science·José V HernándezDavid A Leigh
Dec 14, 2004·Angewandte Chemie·Markus AlbrechtRoland Fröhlich
Dec 17, 2004·Journal of the American Chemical Society·Jonathan R NitschkeDavid Gérard
Dec 17, 2004·Organic & Biomolecular Chemistry·Jerome Lacour, Richard Frantz
Feb 11, 2005·Journal of the American Chemical Society·Nathan C GianneschiChad A Mirkin
Feb 23, 2005·Chemical Communications : Chem Comm·Markus AlbrechtRoland Frohlich
Jul 13, 2005·Chemical Communications : Chem Comm·Paul C M van GervenAlan E Rowan
Jul 21, 2005·Journal of the American Chemical Society·Markus AlbrechtRoland Fröhlich
Aug 3, 2005·Proceedings of the National Academy of Sciences of the United States of America·David Schultz, Jonathan R Nitschke
Aug 3, 2005·Chemistry : a European Journal·Christel DolainIvan Huc
Aug 16, 2005·Inorganic Chemistry·Ruifa Zong, Randolph P Thummel
Aug 30, 2005·Nature Materials·José BernáFrancesco Zerbetto
Sep 30, 2005·Journal of the American Chemical Society·Roberta CacciapagliaLuigi Mandolini
Apr 17, 2001·Angewandte Chemie·David A LeighJenny K Y Wong

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Citations

Jul 24, 2010·Nature Chemistry·Victoria E CampbellJonathan R Nitschke
May 5, 2017·Angewandte Chemie·Jake L GreenfieldJonathan R Nitschke
Aug 11, 2006·Organic Letters·Raphael M Bennes, Douglas Philp
Jan 25, 2007·Chemistry : a European Journal·David Schultz, Jonathan R Nitschke
Nov 21, 2007·Angewandte Chemie·Rupam J Sarma, Jonathan R Nitschke
Apr 5, 2008·Chemistry : a European Journal·Marie HutinJonathan R Nitschke
Nov 19, 2009·Chemical Communications : Chem Comm·Jérôme Lacour, Delphine Moraleda
Apr 16, 2010·Chemical Communications : Chem Comm·Lindsay BainMartina Whitehead
Nov 14, 2006·Proceedings of the National Academy of Sciences of the United States of America·Marie HutinJonathan R Nitschke
May 1, 2012·Organic & Biomolecular Chemistry·Manik Lal Saha, Michael Schmittel
Feb 14, 2013·Chemical Communications : Chem Comm·Yuan WuDan Li
Apr 12, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·T Riis-JohannessenCraig R Rice
Jan 5, 2013·Chemical Communications : Chem Comm·Tanya K RonsonJonathan R Nitschke
Oct 20, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Oliver R CleggNicholas C Fletcher
May 16, 2009·Chemistry : a European Journal·Victoria E CampbellJonathan R Nitschke
Oct 20, 2020·Chemistry : a European Journal·Antonio SantoroJean-Marie Lehn
Jun 27, 2009·Accounts of Chemical Research·Brian H NorthropPeter J Stang
Aug 26, 2011·Chemical Reviews·Rajesh ChakrabartyPeter J Stang
May 2, 2012·Journal of the American Chemical Society·Xiao-Ping ZhouChi-Ming Che

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