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A Rational Design of Catechol‐Based Compounds: An Experimental and Theoretical Study of Optical Properties
Author(s) -
Aronica Christophe,
VenancioMarques Anna,
Chauvin Jérôme,
Robert Vincent,
Lemercier Gilles
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200802325
Subject(s) - sonogashira coupling , catechol , chromophore , chemistry , rational design , computational chemistry , triple bond , polar effect , combinatorial chemistry , photochemistry , organic chemistry , materials science , nanotechnology , double bond , palladium , catalysis
Finely tuned optical properties : The optical properties of substituted protected catechol derivatives can be fine‐tuned (see scheme; TBDMS= tert ‐butyldimethylsilyloxy). The DFT‐calculated polarisabilities are compared with experimental data.The synthesis and optical properties of 4,5‐disubstituted ( tert ‐butyldimethylsilyloxy)‐protected catechol derivatives are reported. One or two carboncarbon triple bond functions were introduced through the Sonogashira cross‐coupling reaction. The effects on the optical properties of monosubstitution at the 4‐position or disubstitution at the 4‐ and 5‐positions of these catechol derivatives with electron‐withdrawing or ‐donating substituents have been investigated. The experimental chemical‐structure–polarisability relationship has been studied by using the Lippert–Mataga correlation and compared with the results of a theoretical study carried out with DFT calculations. These compounds are promising candidates for the fine‐tuning of internal charge transfer, but also as potential non‐linear chromophores and ligands within multifunctional coordination complexes.