Silver(I) Mediated Folding of a Molecular Basket

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Abstract

We have investigated Ag(I) mediated folding of a tridentate compound, containing three pyridine flaps tethered to a semirigid scaffold, into a molecular basket, using both experimental and theoretical methods. The basket formation has been shown to be highly favorable in organic media (ΔG° = −7.2 kcal/mol), with the assembly process allowing for another ligand to bind preferentially on the outer side.

Citing Articles

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This article has been cited by 6 ACS Journal articles (5 most recent appear below).

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  Benzocyclotrimers: From the Mills−Nixon Effect to Gas Hosting

  Fabrizio Fabris, Cristiano Zonta, Giuseppe Borsato, and Ottorino De Lucchi
  Accounts of Chemical Research2011 44 (6), 416-423

  • Benzocyclotrimers: From the Mills−Nixon Effect to Gas Hosting

    Fabrizio Fabris, Cristiano Zonta, Giuseppe Borsato, and Ottorino De Lucchi
    Accounts of Chemical Research2011 44 (6), 416-423

    The formal annulation of three bicylic olefins yields a class of molecules termed benzocyclotrimers (BCTs), which have unusual electronic properties. The bonds in the central aromatic ring, for example, alternate in length: rather than resembling a ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Stereoselective Cyclotrimerization of Enantiopure Iodonorbornenes Catalyzed by Pd Nanoclusters for C₃ or C_3v Symmetric syn-Tris(norborneno)benzenes

  Shuhei Higashibayashi, A. F. G. Masud Reza and Hidehiro Sakurai
  The Journal of Organic Chemistry2010 75 (13), 4626-4628

  • Stereoselective Cyclotrimerization of Enantiopure Iodonorbornenes Catalyzed by Pd Nanoclusters for C₃ or C_3v Symmetric syn-Tris(norborneno)benzenes

    Shuhei Higashibayashi, A. F. G. Masud Reza and Hidehiro Sakurai
    The Journal of Organic Chemistry2010 75 (13), 4626-4628

    C3 or C3v symmetric enantiopure syn-tris(norborneno)benzenes with various functional groups were synthesized through Pd-catalyzed cyclotrimerization of enantiopure iodonorbornenes. The generality of Pd-catalyzed cyclotrimerization for syn-tris(norborneno)...

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• 

  Encapsulation of Guests within a Gated Molecular Basket: Thermodynamics and Selectivity

  Bao-Yu Wang, Xiaoguang Bao, Sandra Stojanović, Christopher M. Hadad and Jovica D. Badjić
  Organic Letters2008 10 (23), 5361-5364

  • Encapsulation of Guests within a Gated Molecular Basket: Thermodynamics and Selectivity

    Bao-Yu Wang, Xiaoguang Bao, Sandra Stojanović, Christopher M. Hadad and Jovica D. Badjić
    Organic Letters2008 10 (23), 5361-5364

    Molecular basket 1 has been designed to contain a set of aromatic gates, each with rotational mobility restricted via intramolecular hydrogen bonding. This structural, yet dynamic, feature of the host has been revealed to permit the formation of a ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
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  A 3-fold “Butterfly Valve” in Command of the Encapsulation’s Kinetic Stability. Molecular Baskets at Work

  Bao-Yu Wang, Xiaoguang Bao, Zhiqing Yan, Veselin Maslak, Christopher M. Hadad and Jovica D. Badjić
  Journal of the American Chemical Society2008 130 (45), 15127-15133

  • A 3-fold “Butterfly Valve” in Command of the Encapsulation’s Kinetic Stability. Molecular Baskets at Work

    Bao-Yu Wang, Xiaoguang Bao, Zhiqing Yan, Veselin Maslak, Christopher M. Hadad and Jovica D. Badjić
    Journal of the American Chemical Society2008 130 (45), 15127-15133

    Molecular basket 1, composed of a semirigid tris-norbornadiene framework and three revolving pyridine-based gates at the rim, has been built to “dynamically” enclose space and as such regulate molecular encapsulation. The gates were shown to fold via ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Molecular Encapsulation via Metal-to-Ligand Coordination in a Cu(I)-Folded Molecular Basket

  Stephen Rieth, Zhiqing Yan, Shijing Xia, Matthew Gardlik, Albert Chow, Gideon Fraenkel, Christopher M. Hadad and Jovica D. Badjić
  The Journal of Organic Chemistry2008 73 (13), 5100-5109

  • Molecular Encapsulation via Metal-to-Ligand Coordination in a Cu(I)-Folded Molecular Basket

    Stephen Rieth, Zhiqing Yan, Shijing Xia, Matthew Gardlik, Albert Chow, Gideon Fraenkel, Christopher M. Hadad and Jovica D. Badjić
    The Journal of Organic Chemistry2008 73 (13), 5100-5109

    A molecular basket, composed of a semirigid C3v symmetric tris-norbornadiene framework and three pyridine flaps at the rim, has been shown to coordinate to a Cu(I) cation and thereby fold in a multivalent fashion. The assembly was effective (Ka = 1.73 ± ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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