Chiral 1,2- and 1,3-Diol-Functionalized Chromophores as Lego Building Blocks for Coupled Structures
journal contributionposted on 2005-10-14, 00:00 authored by Stefan Spange, Katja Hofmann, Bernhard Walfort, Tobias Rüffer, Heinrich Lang
Chiral nitroanilines containing 1,2- or 1,3-diol functionalities have been synthesized by nucleophilic aromatic substitution of fluoronitroanilines with 1-aminopropane-2,3-diols and 2-aminopropane-1,3-diol in the melt. X-ray structure analyses confirm retention of the configuration of the chiral center. The novel chromophores are suitable to link reversibly to various substituted arylboronic acids which allows the construction of new solvatochromic sensor molecules suitable to response to solvent and anion coordination by fluoride. The solvatochromism of the new compounds has been studied using the Kamlet−Taft LSE relationship.
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fluoronitroanilinecompoundarylboronic acidschiral centerKamletretentionLSEChromophoreLego Building Blocksanion coordinationStructures Chiral nitroanilineslink reversiblysolvatochromic sensor moleculesfluoriderelationshipdiolfunctionalitienovel chromophoresconstructionsubstitutionanalysesconfigurationresponsenucleophilicaminopropanesolvatochromism