Hydroxy-Functionalized Bipyridine and Tris(bipyridine)metal Chromophores: Synthesis and Optical Properties

A new family of symmetrically and unsymmetrically‐substituted 4,4′‐bis[(dialkylamino)styryl]‐2,2′‐bipyridine ligands, containing 1−4 hydroxy groups on their dialkylamino moieties, have been synthesized. They are readily prepared in good to excellent yields from 4,4′‐dimethyl‐2,2′‐bipyridine and tetr...

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Bibliographic Details
Published in:European journal of organic chemistry 2002-09, Vol.2002 (17), p.3024-3033
Main Authors: Le Bouder, Thomas, Viau, Lydie, Guégan, Jean-Paul, Maury, Olivier, Le Bozec, Hubert
Format: Article
Language:English
Subjects:
Chemical Sciences
Donor-acceptor systems
Nitrogen heterocycles
Nonlinear opties
Ruthenium
Zinc
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Summary:A new family of symmetrically and unsymmetrically‐substituted 4,4′‐bis[(dialkylamino)styryl]‐2,2′‐bipyridine ligands, containing 1−4 hydroxy groups on their dialkylamino moieties, have been synthesized. They are readily prepared in good to excellent yields from 4,4′‐dimethyl‐2,2′‐bipyridine and tetrahydropyranyloxy‐protected [(hydroxyalkyl)amino]benzaldehydes. These chromophores display excellent thermal stabilities, with decomposition temperatures of up to 310 °C. The influence of the OH groups on the optical properties (absorption and emission) is discussed. The synthesis of the corresponding heteroleptic and homoleptic tris(bipyridine)metal(II) complexes (M2+ = Ru2+, Zn2+), as building blocks for the elaboration of macromolecular NLO‐phores, is also described. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
ISSN:1434-193X
1099-0690
DOI:10.1002/1099-0690(200209)2002:17<3024::AID-EJOC3024>3.0.CO;2-K