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Hydroxy‐Functionalized Bipyridine and Tris(bipyridine)metal Chromophores: Synthesis and Optical Properties
Author(s) -
Le Bouder Thomas,
Viau Lydie,
Guégan JeanPaul,
Maury Olivier,
Le Bozec Hubert
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200209)2002:17<3024::aid-ejoc3024>3.0.co;2-k
Subject(s) - chemistry , chromophore , bipyridine , 2,2' bipyridine , tris , metal , polymer chemistry , 4,4' bipyridine , photochemistry , organic chemistry , molecule , crystal structure , hydrogen bond , biochemistry
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 (M 2+ = Ru 2+ , Zn 2+ ), as building blocks for the elaboration of macromolecular NLO‐phores, is also described. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)