| Abstract
| - The selective cleavage of arylmethyl thioethers provides a convenient protocol for the synthesis ofall-E isomers of α,ω-bis(thioacetyl)oligophenyenevinylene molecules (OPVs). The S-methyl groupis tolerant of Wittig-type and Heck-type reactions for forming OPV structures and can be convertedto the S-acetyl group by treatment with sodium thiomethoxide and acetyl chloride. The thermalconditions of the deprotection/reprotection step concurrently isomerize the conjugated chromophoreto the all-E isomer, regardless of the stereochemistry of the starting olefins. This approach isdemonstrated for a variety of linear and [2.2]paracyclophane containing OPVs, which have beencharacterized by electrochemical and spectroscopic techniques. Additionally, these S-acetyl-terminated OPVs self-assemble on gold surfaces. Monolayers containing these molecules werecharacterized by water contact angle measurements, ellipsometry, and X-ray photoelectronspectroscopy.
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