The Introduction of Asymmetry into Alkyl‐Decorated Fréchet‐Type Dendrons

A strategy for the introduction of asymmetry into Frechet-type dendrons bearing n-alkyl chains is described. Starting from a methyl 3,5-dihydroxybenzoate core, 3,5-bis(octyloxyphenyl)methoxy and 3,5-bis(alkoxyphenyl)methoxy units are introduced in a stepwise manner. The method is illustrated by the syntheses of four representative compounds having mixed n-octyl/n-butyl, n-octyl/n-hexyl, n-octyl/n-heptyl and n-octyl/n-dodecyl substituents. The new compounds have been characterized by spectroscopic and mass spectrometric techniques.

[1]  M. Neuburger,et al.  Self-assembled monolayers as two-dimensional crystals: relationship to three-dimensional crystals , 2007 .

[2]  C. Housecroft,et al.  Self‐Organized Monolayers: A Route to Conformational Switching and Read‐Out of Functional Supramolecular Assemblies by Scanning Probe Methods , 2006 .

[3]  H. Güntherodt,et al.  Octyl-decorated Fréchet-type dendrons: a general motif for visualisation of static and dynamic behaviour using scanning tunnelling microscopy? , 2005, Chemistry.

[4]  M. Neuburger,et al.  Conformational analysis of self-organized monolayers with scanning tunneling microscopy at near-atomic resolution. , 2005, Journal of the American Chemical Society.

[5]  C. Housecroft,et al.  Monitoring conformational diversity in self-organised monolayers with scanning tunnelling microscopy at near atomic resolution. , 2004, Chemical communications.

[6]  E. Carreira,et al.  Mild cleavage of aryl mesylates: methanesulfonate as potent protecting group for phenols. , 2004, Organic letters.

[7]  H. Güntherodt,et al.  Hourglass-Shaped Dendrimers on Surfaces: A Comparison of Different Scanning-Tunneling-Microscopy Approaches , 2002 .

[8]  J. Fréchet,et al.  Convergent dendrons and dendrimers: from synthesis to applications. , 2001, Chemical reviews.

[9]  D. Seebach,et al.  Dendritic TADDOLs: Synthesis, Characterization and Use in the Catalytic Enantioselective Addition of Et2Zn to Benzaldehyde , 1999 .

[10]  Jieping Zhu,et al.  A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction , 1995 .

[11]  C. Hawker,et al.  Preparation of polymers with controlled molecular architecture. A new convergent approach to dendritic macromolecules , 1990 .

[12]  G. Gokel,et al.  Crown-cation complex effects. 8. Reactions of crown ether activated tert-butoxide ion , 1978 .

[13]  G. Gokel,et al.  Principles and Synthetic Applications in Crown Ether Chemistry , 1976 .

[14]  Kimoon Kim,et al.  Erratum to: Rotaxane Dendrimers. , 2003, Topics in current chemistry.

[15]  A. Schlüter.  Dendrimers with Polymeric Core: Towards Nanocylinders , 1998 .

[16]  C. Hawker,et al.  A new convergent approach to monodisperse dendritic macromolecules , 1990 .