Concave-Convex π-π Template Approach Enables the Synthesis of [10]Cycloparaphenylene-Fullerene [2]Rotaxanes

Journal of the American Chemical Society
Youzhi XuMax von Delius

Abstract

The cycloparaphenylenes (CPPs) are a class of strained macrocycles that until 2008 were considered beyond the reach of organic synthesis. With its cyclic array of ten para-substituted phenylene rings, [10]CPP possesses a concave π-system that is perfectly preorganized for the strong supramolecular association of convex fullerenes such as C60. Although mechanically interlocked CPP architectures have been observed in the gas phase, the rational synthesis of bulk quantities has not been achieved yet, which is likely due to the fact that conventional template strategies are not amenable to CPP rings that lack heteroatoms. Here, we report the synthesis of two [2]rotaxanes in which a [10]CPP ring binds to a central fullerene bis-adduct and is prevented from dethreading by the presence of two bulky fullerene hexakis-adduct stoppers. The final step in the rotaxane synthesis is surprisingly efficient (up to ca. 40% yield) and regioselective because the fullerene acts as an efficient convex template, while [10]CPP acts as a supramolecular directing group, steering the reaction at the central fullerene exclusively toward two trans regioisomers. Comprehensive physicochemical studies confirmed the interlocked structure, shed light on the dy...Continue Reading

References

Oct 21, 2000·Accounts of Chemical Research·D M Guldi, M Prato
Aug 22, 2003·Nature·Pall ThordarsonRoeland J M Nolte
Feb 16, 2006·Journal of the American Chemical Society·Vincent AucagneD Barney Walker
Apr 26, 2006·Chemical Society Reviews·Dirk M GuldiChristian Ehli
Sep 21, 2007·Journal of the American Chemical Society·Sourav SahaAlberto Credi
Dec 6, 2008·Journal of the American Chemical Society·Ramesh JastiCarolyn R Bertozzi
Jul 10, 2009·Chemical Society Reviews·James D CrowleyRoy T McBurney
Jul 10, 2009·Chemical Society Reviews·J Fraser Stoddart
Jul 10, 2009·Angewandte Chemie·Hiroko TakabaKenichiro Itami
Dec 17, 2009·Angewandte Chemie·Shigeru YamagoTakahiro Iwamoto
Dec 22, 2009·Chemical Society Reviews·Xiang Ma, He Tian
Jan 9, 2010·Journal of the American Chemical Society·Youjun HeYongfang Li
Mar 24, 2010·Chemical Society Reviews·Kevin D Hänni, David A Leigh
Apr 20, 2010·Nature Nanotechnology·Damian AckermannMichael Famulok
Nov 19, 2010·Chemical Communications : Chem Comm·Aurelio Mateo-Alonso
May 6, 2011·Journal of the American Chemical Society·Takahiro IwamotoShigeru Yamago
Nov 26, 2011·Chemical Society Reviews·Ali CoskunBartosz A Grzybowski
Sep 15, 2012·Angewandte Chemie·Chenfeng KeJ Fraser Stoddart
Nov 8, 2012·Journal of the American Chemical Society·Jianlong XiaRamesh Jasti
Nov 30, 2012·Accounts of Chemical Research·Graeme T Spence, Paul D Beer
Sep 10, 2013·Chemical Communications : Chem Comm·Francesco ScarelAurelio Mateo-Alonso
Apr 9, 2014·Accounts of Chemical Research·Matthew J Langton, Paul D Beer
Feb 18, 2015·Accounts of Chemical Research·Matthew R Golder, Ramesh Jasti
Apr 29, 2015·Chemical Society Reviews·Evan R Darzi, Ramesh Jasti
Apr 29, 2015·Angewandte Chemie·Michael FranzRik R Tykwinski
Jul 1, 2015·The Journal of Physical Chemistry. a·Douglas A HinesPrashant V Kamat
Aug 15, 2015·Chemical Society Reviews·Emilio M Pérez, Nazario Martín
Sep 9, 2015·Chemical Reviews·Sundus Erbas-CakmakAlina L Nussbaumer
Jan 12, 2016·Journal of the American Chemical Society·Levon D MovsisyanHarry L Anderson
Oct 21, 2016·Angewandte Chemie·David A Leigh
Feb 9, 2017·Nature Communications·Jan HermannAlexandre Tkatchenko
Apr 28, 2017·Chemical Society Reviews·James E M LewisStephen M Goldup
Jun 1, 2017·Accounts of Chemical Research·Dominik Wendinger, Rik R Tykwinski
Jul 19, 2017·Chemistry : a European Journal·Emilio M Pérez
Oct 19, 2017·Angewandte Chemie·Philipp J Altmann, Alexander Pöthig
Dec 1, 2017·Journal of the American Chemical Society·Eiichi KayaharaShigeru Yamago
Jan 18, 2018·Journal of the American Chemical Society·Timothy A BarendtPaul D Beer
May 2, 2018·Nature Chemistry·Kelong ZhuStephen J Loeb

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Citations

Oct 17, 2018·Angewandte Chemie·Tobias A SchaubRamesh Jasti
Jan 24, 2019·Chemistry : a European Journal·Serxho Selmani, Derek J Schipper
Jun 14, 2019·Angewandte Chemie·Youzhi Xu, Max von Delius
Sep 27, 2019·Angewandte Chemie·Anastasios StergiouNikos Tagmatarchis
Feb 23, 2020·Chemical Communications : Chem Comm·Shun-Ze ZhanDan Li
Mar 25, 2020·Chemistry : a European Journal·Jeff M Van RadenRamesh Jasti
Jul 30, 2020·Angewandte Chemie·Luka ÐorđevićMaurizio Prato
Oct 28, 2019·Frontiers in Chemistry·Dapeng LuPingwu Du
Feb 15, 2020·Chemical Science·Sandip V MulayOri Gidron
Jul 20, 2019·Science·Jeff M Van Raden, Ramesh Jasti
Aug 17, 2019·Chemical Society Reviews·Sofía Mena-Hernando, Emilio M Pérez
Jan 31, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Artur KasprzakAnna M Nowicka
Feb 23, 2021·Angewandte Chemie·Adrian Saura-SanmartinJose Berna
Apr 8, 2021·Chemistry : a European Journal·Marine RémyJean-François Nierengarten
May 20, 2021·Chemical Society Reviews·Giorgio OlivoStefano Di Stefano
Apr 23, 2021·Angewandte Chemie·Niklas GrabickiOliver Dumele
Jun 20, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Anandarao MunakalaRambabu Chegondi
Nov 12, 2019·Journal of the American Chemical Society·Youzhi XuMax von Delius
Dec 5, 2020·ACS Central Science·Tobias Schnitzer, Ghislaine Vantomme
Jan 25, 2020·Organic Letters·Yan MiCheng Yang
Nov 21, 2020·Journal of the American Chemical Society·Catherine A J HooperMichael J Hannon
Apr 19, 2019·Journal of the American Chemical Society·Kabali SenthilkumarMarcin Stępień
Jan 14, 2020·The Journal of Organic Chemistry·Tatsuya KawanishiShigeru Yamago
Oct 19, 2019·The Journal of Organic Chemistry·Jeff M Van RadenRamesh Jasti
Sep 25, 2021·Journal of the American Chemical Society·Oleg BorodinMax von Delius
Nov 27, 2021·ChemPlusChem·Yong Yang, Michal Juríček

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