DABCO-Induced self-assembly of a trisporphyrin double-decker cage: thermodynamic characterization and guest recognition

Journal of the American Chemical Society
Pablo BallesterChristopher A Hunter

Abstract

This paper describes the thermodynamic characterization of the self-assembly of a Zn trisporphyrin induced by coordination with 1,4-diazabicyclo[2.2.2]octane (DABCO) to form a stable 2:3 double-decker molecular coordination cage that recognizes benzene-1,3,5-tricarboxamides. The self-assembly process has been studied using UV-vis and (1)H NMR spectroscopy and quantitatively characterized in terms of a single stability constant that describes the strength of the individual coordination interactions and two effective molarities (EM) that describe the additional stability imparted by intramolecular cyclization. The EM values of the two consecutive cyclic intramolecular interactions are very similar. At micromolar concentrations, the formation of the fully assembled coordination cage is highly favored over the formation of intermediate species stabilized by fewer interactions, and so self-assembly is an all-or-nothing process. In contrast, at millimolar concentrations, the relative stability of intermediate species increases, leading to a stepwise self-assembly process, and a 2:2 intermediate can be clearly identified using (1)H NMR spectroscopy. The molecular recognition of benzene-1,3,5-tricarboxamides by the cage was investigate...Continue Reading

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Citations

Aug 26, 2011·Chemical Reviews·Rajesh ChakrabartyPeter J Stang
Nov 26, 2008·Chemical Communications : Chem Comm·Juan EtxebarriaPablo Ballester
Feb 8, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Evgeny A Katayev, Markus B Schmid
Aug 9, 2011·Physical Chemistry Chemical Physics : PCCP·Ruslan R KashapovAlexander I Konovalov
Jul 8, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·T T DangB Ventura
Jul 22, 2014·Chemistry : a European Journal·Stéphanie DurotBarbara Ventura
Aug 15, 2018·Organic & Biomolecular Chemistry·Rhys B MurphyMartin R Johnston
Jul 6, 2007·Chemistry : a European Journal·Marga C LensenRoeland J M Nolte
Aug 31, 2007·Organic & Biomolecular Chemistry·Maria Angeles Sarmentero, Pablo Ballester
Jan 18, 2008·Journal of Molecular Recognition : JMR·Oksana Okhrimenko, Ilian Jelesarov
Apr 3, 2008·Chemistry : a European Journal·Lucia FlamigniPablo Ballester
May 29, 2008·Angewandte Chemie·Markus HoffmannHarry L Anderson
Jan 30, 2010·Chemistry : a European Journal·Peter OsswaldFrank Würthner
Jan 13, 2010·Chemical Communications : Chem Comm·Victoria L GundersonMichael R Wasielewski
May 23, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Elena A MikhalitsynaIrina P Beletskaya
Aug 14, 2019·Chemistry : a European Journal·Rhys B MurphyMartin R Johnston
Feb 18, 2011·Angewandte Chemie·Gianfranco Ercolani, Luca Schiaffino
Feb 20, 2007·Angewandte Chemie·Hiroshi KatagiriEiji Yashima
Sep 5, 2015·Chemistry : a European Journal·Pablo BallesterValérie Heitz
Aug 30, 2018·Chemical Science·T H NgoS M Goldup
May 12, 2012·Chemistry : a European Journal·Adriana IordacheChristophe Bucher
Nov 29, 2014·Angewandte Chemie·Luis MoreiraJean-François Nierengarten
Mar 13, 2008·Science and Technology of Advanced Materials·Katsuhiko ArigaSomobrata Acharya
May 6, 2011·Angewandte Chemie·Johannes K SprafkeHarry L Anderson
Sep 10, 2013·Chemical Communications : Chem Comm·Francesco ScarelAurelio Mateo-Alonso
Jan 1, 2021·European Journal of Organic Chemistry·Kathleen StoutJohannes A A W Elemans
Mar 24, 2009·Chemical Reviews·Irina BeletskayaChristine Stern
Jul 29, 2009·The Journal of Physical Chemistry. B·Almudena González-AlvarezPablo Ballester
Aug 4, 2010·The Journal of Organic Chemistry·Michael Schmittel, Soumen K Samanta
Jul 16, 2014·Chemical Reviews·Stéphanie DurotValérie Heitz
Mar 4, 2015·Journal of the American Chemical Society·Seda CantekinRoeland J M Nolte
Dec 23, 2010·Langmuir : the ACS Journal of Surfaces and Colloids·Usha DeviSimon J Webb
Dec 5, 2013·Journal of the American Chemical Society·Soumen K Samanta, Michael Schmittel
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Aug 26, 2011·The Journal of Organic Chemistry·Soumen K SamantaMichael Schmittel
Nov 23, 2019·Accounts of Chemical Research·Huub M M Ten Eikelder, Albert J Markvoort

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