Mindy Levine -  Synthesis of a Near-Infrared Emitting Squaraine Dye in an Undergraduate Organic Laboratory

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      Publication Details (including relevant citation   information):

       
    •     By Marks, Patrick;     Levine,     Mindy 
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    •     From Journal of Chemical     Education (2012), 89(9), 1186-1189.  

      Abstract:

        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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