Synthesis 2006(9): 1504-1512  
DOI: 10.1055/s-2006-926439
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Ditopic and Tripodal 1,2,4-Triazole- and Tetrazole-Based Ligands for Coordination Chemistry

Yves Bolanda, Pascale Hertsensa, Jacqueline Marchand-Brynaertb, Yann Garcia*a
a Unité de Chimie des Matériaux Inorganiques et Organiques, Département de Chimie, Faculté des Sciences, Université catholique de Louvain­, Place L. Pasteur 1, 1348 Louvain-la-Neuve, Belgium
b Unité de Chimie Organique et Médicinale, Département de Chimie, Faculté des Sciences, Université catholique de Louvain, Place L. Pasteur 1, 1348 Louvain-la-Neuve, Belgium
Fax: +32(10)472831; e-Mail: garcia@chim.ucl.ac.be;
Further Information

Publication History

Received 12 October 2005
Publication Date:
11 April 2006 (online)

Zoom Image

Abstract

The practical synthesis of two new classes of polytopic azole-based ligands is reported. The synthesis of the precursor amines was achieved by substitution of a leaving group by an azide followed by reduction with triphenylphosphine and water. Another efficient method employs a Mitsunobu coupling with phthalimide allowing the conversion of a primary alcohol into a primary amine. The triazole and tetrazole were obtained by cyclization of these amine precursors. The first family consisted of ditopic ligands containing both 1-R-tetrazole and 4-R-1,2,4-triazole moieties linked by an alkyl spacer, while the second consists of branched ligands with three azole cycles linked to a benzene core through ether bonds. Both classes are suitable for building multidimensional polynuclear coordination assemblies and for the observation of thermal spin state crossover behavior with iron(II) ions.