Iron(II) and zinc(II) monohelical binaphthyl-salen complexes with overlapping benz[a]anthryl sidearms

The synthesis of the polyaromatic aldehyde 1-hydroxybenz[a]anthracene-2-carboxaldehyde is reported via a seven step protocol from 9,10-dihydroanthracene, with an overall yield of 30%. Two equivalents of the aldehyde are condensed with (R)-1,1'-binaphthyl-2,2'-diamine to produce a new binap...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2007-01 (15), p.1520-1527
Main Authors: Wiznycia, Alexander V, Desper, John, Levy, Christopher J
Format: Article
Language:English
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Summary:The synthesis of the polyaromatic aldehyde 1-hydroxybenz[a]anthracene-2-carboxaldehyde is reported via a seven step protocol from 9,10-dihydroanthracene, with an overall yield of 30%. Two equivalents of the aldehyde are condensed with (R)-1,1'-binaphthyl-2,2'-diamine to produce a new binaphthyl-salen ligand, which is subsequently complexed to iron(II) and zinc(II) ions. The ligand and complexes are characterized by single-crystal X-ray crystallography. The complexes have distinct helical structures with overlapping benz[a]anthryl sidearms, and only M-helices are observed. The ligand and complexes are further characterized by solution (1)H and (13)C NMR spectroscopy as well as UV-visible and ECD spectroscopies. These studies indicate that there is a single component in solution, consistent with the solid state characterization.
ISSN:1477-9226
1477-9234
DOI:10.1039/b700001d