Progress on the synthesis of a symmetrical dihydroxydibenzo-26-crown-8 : an honors thesis (HONRS 499)

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Authors
Gilbert, Kyle R.
Advisor
Sousa, Lynn R.
Issue Date
2007
Keyword
Degree
Thesis (B.?.)
Department
Honors College
Other Identifiers
Abstract

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.