Publication Details (including relevant citation information):
- By Marks, Patrick; Levine, Mindy
- From Journal of Chemical Education (2012), 89(9), 1186-1189.
Squaraines are a class of org. fluorophores that possess unique photophys. properties, including strong near-IR absorption and emission. The synthesis of many squaraines involves the condensation of an electron-rich arom. ring with squaric acid. These reactions are generally refluxed overnight in a benzene-butanol solvent mixt. Reported herein are modifications to the synthesis of a squaraine dye that allowed the expt. to be performed in an undergraduate lab. setting. The desired compd. was formed after a 2-h reflux, using toluene as a co-solvent rather than the more toxic benzene. Moreover, the photophys. properties of the synthesized squaraine compd. were analyzed in a sep. lab. period and led to important pedagogical opportunities about the absorption and fluorescence of org. compds.
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