Issue 22, 2009
From the journal:

Organic & Biomolecular Chemistry

Four-fold click reactions: Generation of tetrahedral methane- and adamantane-based building blocks for higher-order molecular assemblies†

Oliver Plietzsch,a   Christine Inge Schilling,a   Mariyan Tolev,ab   Martin Nieger,c   Clemens Richert,ab   Thierry Muller*a  and  Stefan Bräse*a  

* Corresponding authors

a Institut für Organische Chemie and Center for Functional Nanostructures (CFN), Universität Karlsruhe (TH) – Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, Karlsruhe, Germany
E-mail: Stefan.Braese@kit.edu
Fax: +49 (0)721 608 8581
Tel: +49 (0)721-608-2902

b Institut für Organische Chemie, Universität Stuttgart, Stuttgart, Germany

c Laboratory of Inorganic Chemistry, University of Helsinki, Helsinki, Finland

Abstract

A modular concept for the generation of achiral and chiral non-racemic tetrahedral tectons from common precursors was developed. The tectons presented here are based on tetraphenylmethane or 1,3,5,7-tetraphenyladamantane core structures. They are obtained through high-yielding four-fold click reactions, using either the tetraazido or the tetraalkyne precursors. In most cases, the tetratriazoles are obtained as pure products after simple washing with water and methanol. The side chains of the tectons prepared include a self-complementary DNA dimer, obtained from a 3′-azidonucleoside and a phosphoramidite. The concept allows for a variation of the “sticky ends”, leading to tecton or ligand libraries.

Graphical abstract: Four-fold click reactions: Generation of tetrahedral methane- and adamantane-based building blocks for higher-order molecular assemblies

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Article information

DOI
https://doi.org/10.1039/B912189G
Article type
Paper
Submitted
22 Jun 2009
Accepted
04 Aug 2009
First published
14 Sep 2009

Org. Biomol. Chem., 2009,7, 4734-4743

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Four-fold click reactions: Generation of tetrahedral methane- and adamantane-based building blocks for higher-order molecular assemblies

O. Plietzsch, C. I. Schilling, M. Tolev, M. Nieger, C. Richert, T. Muller and S. Bräse, Org. Biomol. Chem., 2009, 7, 4734 DOI: 10.1039/B912189G

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