New Rebek imide-type receptors for adenine featuring acetylene-linked pi-stacking platforms.

Rebek imide-type molecular clefts with pi-stacking platforms attached to the imide scaffold by an acetylene linker have been prepared by Sonogashira cross-coupling. In the solid state, a novel dimerisation mode for this class of imide receptors was found by crystal structure analysis, whereas efficient 1 : 1 complexation with 9-ethyladenine was observed in CDCl3 solution.

[1]  Raffaella Faraoni,et al.  H-Bonded complexes of adenine with Rebek imide receptors are stabilised by cation?? interactions and destabilised by stacking with perfluoroaromaticsElectronic supplementary information (ESI) available: Protocols for the synthesis of 1a?i; description of 1H NMR binding titrations, determination of d , 2004 .

[2]  F. Diederich,et al.  Rebek imides and their adenine complexes: preferences for Hoogsteen binding in the solid state and in solution. , 2002, Chemistry.

[3]  H. Bergmann,et al.  Enantioselective Intramolecular [2+2]‐Photocycloaddition Reactions in Solution , 2000 .

[4]  C. Hunter,et al.  COOPERATIVE INTERACTIONS IN A TERNARY MIXTURE , 1998 .

[5]  H. Bestmann,et al.  An Improved One-pot Procedure for the Synthesis of Alkynes from Aldehydes , 1996 .

[6]  A. Yanagisawa,et al.  Catalytic Enantioselective Protonation of Simple Enolate with Chiral Imide1 , 1995 .

[7]  J. Rebek,et al.  A new chiral auxiliary for asymmetric thermal reactions: high stereocontrol in radical addition, allylation, and annulation reactions , 1992 .

[8]  K. Parris,et al.  New Chiral Auxiliaries for Enolate Alkylations , 1990 .

[9]  J. Rebek Molecular Recognition with Model Systems , 1990 .

[10]  J. Rebek,et al.  Molecular recognition with convergent functional groups. VII. Energetics of adenine binding with model receptors , 1989 .

[11]  J. Rebek Molecular recognition: Model studies with convergent functional groups , 1988, Journal of molecular recognition : JMR.

[12]  K. Parris,et al.  Molecular Recognition: Stacking Interactions Influence Watson-Crick vs. Hoogsteen Base-Pairing in a Model for Adenine Receptors , 1987 .

[13]  L. d’Haenens,et al.  An Efficient Preparation and the Intramolecular Cyclopropanation of a-Diazo-3-Ketophosphonates and a-Diazophosphonoacetates , 1984 .

[14]  E. V. D. Eycken,et al.  Photoinduced Wolff Rearrangement of α-Diazo-β-Ketophosphonates : A Novel Entry into Substituted Phosphonoacetates , 1984 .

[15]  A. Rich,et al.  Specific Hydrogen Bonding of Barbiturates to Adenine Derivatives , 1968, Nature.

[16]  R. C. Fahey,et al.  Polar Addition of Hydrogen Halides onto Olefins , 1964 .