We are interested in a very rare class of oxygen-containing charged polycyclic aromatic hydrocarbons containing the 6-aryldibenzo[b,d]pyrylium moiety. This moiety is isomeric with the 9-aryldibenzo[b,e]pyrylium (xanthylium) unit, found in numerous important dyes, such as rhodamine. This unit is also a further benzannulated analog of the flavylium ion, found in many naturally occurring pigments, such as anthocyanins.  We report the synthesis of several new 6-aryldibenzo[b,d]pyrylium salts as well as their reversible spectroscopic and optical character in varying pH environments (halochromism).   Progress toward the synthesis and study of other analogs containing longer conjugations pathways will also be reported. Reversible disruption of conjugation, and thus intramolecular charge transfer, occurs upon addition of a nucleophile to these compounds and we are exploring the structures of these products as well.

Synthesis and halochromism of 6-aryldibenzo[<i>b</i>,<i>d</i>]pyrylium salts

245th National Meeting (2013)

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Synthesis and halochromism of 6-aryldibenzo[b,d]pyrylium salts