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Synthesis of Chemiluminescent Esters: A Combinatorial Synthesis Experiment for Organic Chemistry Students
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Abstract
In this laboratory exercise, a peroxyoxalate chemiluminescence experiment has been integrated with a combinatorial synthesis experiment. Students prepare a number of esters, in reactions between acyl chlorides and phenols, and test the compounds for chemiluminescence. If the experiment is parallel combinatorial synthesis, each student prepares one to two esters; if the experiment is mix-and-split combinatorial synthesis, each student prepares two mixtures of esters. Results from the entire class are combined, and based on the results, the students identify general structural features of an active (chemiluminescent) ester. In addition to rubrene, which emits the most intense light, a number of inexpensive fluorophores are suitable for this experiment including chlorophyll and anthracene. The laboratory exercise is suitable for introductory organic chemistry students and can be modified for more advanced students.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Inquiry-Based / Discovery LearningKeywords (Subject):
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- Received: August 03, 2009
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