Département de chimie moléculaire

The optical properties of substituted protected catechol derivs. can be fine-tuned (see scheme; TBDMS=tert-butyldimethylsilyloxy). The DFT-calcd. polarizabilities are compared with exptl. data. The synthesis and optical properties of 4,5-disubstituted (tert-butyldimethylsilyloxy)-protected catechol derivs. are reported. One or two carbon-carbon 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 derivs. with electron-withdrawing or -donating substituents have been investigated. The exptl. chem. structure-polarizability relationship has been studied by using the Lippert-Mataga correlation and compared with the results of a theor. study carried out with DFT calcns. These compds. are promising candidates for the fine-tuning of internal charge transfer, but also as potential nonlinear chromophores and ligands within multifunctional coordination complexes. [on SciFinder(R)]