Porphyrinoid rotaxanes: building a mechanical picket fence

Chemical Science
T H NgoStephen M Goldup

Abstract

Building on recent progress in the synthesis of functional porphyrins for a range of applications using the Cu-mediated azide-alkyne cycloaddition (CuAAC) reaction, we describe the active template CuAAC synthesis of interlocked triazole functionalised porphyrinoids in excellent yield. By synthesising interlocked analogues of previously studied porphyrin-corrole conjugates, we demonstrate that this approach gives access to rotaxanes in which the detailed electronic properties of the axle component are unchanged but whose steric properties are transformed by the mechanical "picket fence" provided by the threaded rings. Our results suggest that interlocked functionalised porphyrins, readily available using the AT-CuAAC approach, are sterically hindered scaffolds for the development of new catalysts and materials.

References

Mar 19, 1975·Journal of the American Chemical Society·J P CollmanW T Robinson
Aug 15, 2002·Journal of the American Chemical Society·Koji KanoYasuhisa Kuroda
Aug 28, 2003·Journal of the American Chemical Society·Koji KanoIwao Yamazaki
Nov 13, 2003·Journal of the American Chemical Society·Laura BaldiniRocco Ungaro
Dec 20, 2003·Organic Letters·Tomoya OkuToshikazu Takata
Mar 27, 2004·Chemical Communications : Chem Comm·Marga C LensenAlan E Rowan
Feb 16, 2006·Journal of the American Chemical Society·Vincent AucagneD Barney Walker
Apr 20, 2006·Journal of the American Chemical Society·Pablo BallesterChristopher A Hunter
May 12, 2006·Organic & Biomolecular Chemistry·Takanori KishidaSeiji Shinkai
Oct 20, 2006·Organic Letters·Shinichi SaitoKazuko Nakazono
Nov 30, 2006·Journal of the American Chemical Society·Eric J F KlotzHarry L Anderson
Feb 1, 2007·Chemical Society Reviews·Matthew S Vickers, Paul D Beer
Dec 11, 2007·Organic Letters·Jean-Sébastien MaroisJean-François Morin
Dec 12, 2007·The Journal of Organic Chemistry·Sokkalingam PunidhaMangalampalli Ravikanth
Apr 3, 2008·Chemistry : a European Journal·Lucia FlamigniPablo Ballester
Jun 21, 2008·Chemical Communications : Chem Comm·C M Simon YauHarry L Anderson
Oct 14, 2008·Organic Letters·Michael A FazioDavid I Schuster
Jan 27, 2009·Chemical Society Reviews·Jonathan A FaizJean-Pierre Sauvage
Jul 10, 2009·Chemical Society Reviews·James D CrowleyRoy T McBurney
Jul 10, 2009·Chemical Society Reviews·J Fraser Stoddart
Oct 17, 2009·Journal of the American Chemical Society·Jun TeraoNobuaki Kambe
Mar 24, 2010·Chemical Society Reviews·Kevin D Hänni, David A Leigh
May 4, 2011·The Journal of Physical Chemistry. a·Loïc Le PleuxAnthony Harriman
Mar 23, 2012·The Journal of Physical Chemistry. a·Antoine EggenspillerShunichi Fukuzumi
May 9, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Lydia C GildayPaul D Beer
Jun 20, 2012·Organic Letters·Levon D MovsisyanHarry L Anderson
Sep 18, 2012·Chemistry of Materials : a Publication of the American Chemical Society·Jackson D MegiattoDirk M Guldi
Nov 28, 2012·Angewandte Chemie·Christopher B CaputoDouglas W Stephan
Jan 9, 2013·Organic Letters·Hui ZhangDa-Hui Qu
Jan 12, 2013·Science·Bartosz LewandowskiDavid A Leigh
Aug 14, 2013·Chemistry : a European Journal·Derrick A RobertsSébastien Perrier
Aug 27, 2013·Journal of the American Chemical Society·Joby WinnStephen M Goldup
Sep 13, 2013·Journal of the American Chemical Society·Jianfeng LiW Robert Scheidt
Sep 24, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Lydia C GildayPaul D Beer
Feb 1, 2014·Angewandte Chemie·Alexander Nierth, Michael A Marletta
Feb 25, 2014·Journal of the American Chemical Society·Robert J Bordoli, Stephen M Goldup
Apr 1, 2014·Journal of the American Chemical Society·Guillaume De BoJohn W Ward

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Citations

Oct 31, 2018·Organic & Biomolecular Chemistry·Sean W Hewson, Kathleen M Mullen
Jan 3, 2019·Angewandte Chemie·Florian ModicomStephen M Goldup
Jun 5, 2020·Chemical Communications : Chem Comm·Huynh Thien NgoStephen M Goldup
May 29, 2020·Organic & Biomolecular Chemistry·Pablo Martinez-BulitStephen J Loeb
Jul 9, 2020·Chemical Communications : Chem Comm·He-Ye ZhouChuan-Feng Chen
Jun 9, 2018·Sensors·Huynh Thien NgoGenki Yoshikawa
Apr 9, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ana R L AraújoJosé A S Cavaleiro
Mar 15, 2018·Angewandte Chemie·Mathieu DenisStephen M Goldup
Mar 21, 2018·Journal of the American Chemical Society·James E M LewisStephen M Goldup
Dec 19, 2018·Journal of the American Chemical Society·Martina CirulliMaxie M Roessler

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Methods Mentioned

BETA
size exclusion chromatography

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