Chiral 1,2- and 1,3-diol-functionalized chromophores as Lego building blocks for coupled structures

Stefan Spange; Katja Hofmann; Bernhard Walfort; Tobias Rüffer; Heinrich Lang

doi:10.1021/jo051097g

Chiral 1,2- and 1,3-diol-functionalized chromophores as Lego building blocks for coupled structures

J Org Chem. 2005 Oct 14;70(21):8564-7. doi: 10.1021/jo051097g.

Authors

Stefan Spange¹, Katja Hofmann, Bernhard Walfort, Tobias Rüffer, Heinrich Lang

Affiliation

¹ Department of Polymer Chemistry, Institute of Chemistry, Chemnitz University of Technology, 09111 Chemnitz, Germany. stefan.spange@chemie.tu-chemnitz.de

PMID: 16209609
DOI: 10.1021/jo051097g

Abstract

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.