This Little Light of Mine

This year we revisited the “Synthesis of Chemiluminescent Esters” experiment that was performed by a handful of students in Spring 2008. This time the experiment was performed by 65 sophomore organic chemistry students. We followed the protocol published in the Journal of Chemical Education in 2004: Synthesis of Chemiluminescent Esters: A Combinatorial Synthesis Experiment for Organic Chemistry Students. We did not use 2,3,6-trifluorophenol, since it was the most expensive reagent. Students produced bis(4-nitrophenyl)oxalate (NPO), bis(2,4-dinitrophenyl)oxalate (DNPO), or bis(2,4,6-trichlorophenyl)oxalate (TCPO). They tested the glow of their esters with the following fluorophors: 9,10-diphenylanthracene, rhodamine 6G, and anthracene. We did not use rubrene this year because of the expense. I mixed a stronger batch of acetonitrile and hydrogen peroxide that they suggest (%10 instead of 3%). We performed IR and UV-vis (200 – 500 nm) spectra of student products. If the students had a sufficient quantity of product, they could divide it into three parts and try some with each flourophor. Students inputted their glow information on a spreadsheet that was made available to the whole class. The rhodamine 6G seemed to give the best results. All three of the diester products gave variable results. It is not a “foolproof” experiment, but it was generally successful. As you might imagine, the “wow” factor is quite good. I attempted to run a GC of the student products but it was likely that the diester products did not exit the column.

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