Sandwiching C70 between two crown ether-bound cations: regioselective synthesis, electrochemistry and cation binding properties of C70 bis-crown ether conjugates

Tetrakis-adducts of C70, featuring two covalently attached crown ethers, form stable 1 ∶ 1 and 1 ∶ 2 host–guest complexes with alkali metal cations. A large influence of cation complexation on the first reduction potential of the fullerene was observed.

[1]  T. Aida,et al.  Cyclic Dimers of Metalloporphyrins as Tunable Hosts for Fullerenes: A Remarkable Effect of Rhodium(III) We thank Dr. F. Hasegawa of the Science University of Tokyo for HR-MS measurements. J.-Y.Z. and K.S. thank the JSPS for financial support. , 2001, Angewandte Chemie.

[2]  E. Bakker,et al.  Determination of complex formation constants of lipophilic neutral ionophores in solvent polymeric membranes with segmented sandwich membranes. , 1999, Analytical chemistry.

[3]  F. Diederich,et al.  Cyclophane-type fullerene-dibenzo[18]crown-6 conjugates with trans-1, trans-2, and trans-3 addition patterns: Regioselective templated synthesis, x-ray crystal structure, ionophoric properties, and cation-complexation- dependent redox behavior , 1999 .

[4]  E. Pretsch,et al.  Determination of formal complex formation constants of various Pb2+ ionophores in the sensor membrane phase , 1999 .

[5]  F. Diederich,et al.  ACHIRAL AND CHIRAL HIGHER ADDUCTS OF C70 BY BINGEL CYCLOPROPANATION , 1999 .

[6]  Maurizio Prato,et al.  ENHANCED ACCEPTOR CHARACTER IN FULLERENE DERIVATIVES. SYNTHESIS AND ELECTROCHEMICAL PROPERTIES OF FULLEROPYRROLIDINIUM SALTS , 1998 .

[7]  E. Pretsch,et al.  Ion-Selective Electrodes Based on Two Competitive Ionophores for Determining Effective Stability Constants of Ion−Carrier Complexes in Solvent Polymeric Membranes , 1998 .

[8]  Ernö Pretsch,et al.  Carrier-Based Ion-Selective Electrodes and Bulk Optodes. 1. General Characteristics. , 1997, Chemical reviews.

[9]  F. Diederich,et al.  Multiple Cyclopropanations of C70. Synthesis and characterization of bis‐, tris‐, and tetrakis‐adducts and chiroptical properties of bis‐adducts with chiral addends, including a recommendation for the configurational description of fullerene derivatives with a chiral addition pattern , 1995 .

[10]  A. Hirsch,et al.  Regiochemistry of Multiple Additions to the Fullerene Core: Synthesis of a Th-Symmetric Hexakis adduct of C60 with Bis(ethoxycarbonyl)methylene , 1994 .

[11]  D. A. Gustowski,et al.  Rationalization of the unusual electrochemical behavior observed in lariat ethers and other reducible macrocyclic systems , 1988 .