Progress on the synthesis of a symmetrical dihydroxydibenzo-26-crown-8 : an honors thesis (HONRS 499)
Crown ethers complex selected metal ions, ammonium ions, and potentially, other electron deficient species. With proper functionalization a crown ether might sequester and signal the presence of ions or electron deficient molecules; or from the other perspective, complexed ions or molecules might alter the conformation and properties of the crown ether. The target dihydroxydibenzo-26-crown-8 (1) is designed to be an attachable jaw that can be combined with one or two chromophores to produce fluorescent chemosensors. Progress towards the preparation of this new 26-crown-8 will be presented. Known intermediates such as bis-1,2[2-hydroxyethoxy]benzene(2) and bis-1,2[2-(3-chloro-2-hydroxypopoxy)ethoxy]benzene(3), and a protected bis-1,2[2-(3-chloro-2-hydroxypopoxy)ethoxy]benzene(5) using Dihydropyran have been synthesized. Our approaches to the formation of the "jaw" crown ether (1) by reaction of (2) with (5) will be described.