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ERIC Number: EJ1002726
Record Type: Journal
Publication Date: 2012-Sep
Pages: 4
Abstractor: As Provided
Reference Count: 39
ISSN: ISSN-0021-9584
Synthesis of a Near-Infrared Emitting Squaraine Dye in an Undergraduate Organic Laboratory
Marks, Patrick; Levine, Mindy
Journal of Chemical Education, v89 n9 p1186-1189 Sep 2012
Squaraines are a class of organic fluorophores that possess unique photophysical properties, including strong near-infrared absorption and emission. The synthesis of many squaraines involves the condensation of an electron-rich aromatic ring with squaric acid. These reactions are generally refluxed overnight in a benzene-butanol solvent mixture. Reported herein are modifications to the synthesis of a squaraine dye that allowed the experiment to be performed in an undergraduate laboratory setting. The desired compound was formed after a 2-h reflux, using toluene as a co-solvent rather than the more toxic benzene. Moreover, the photophysical properties of the synthesized squaraine compound were analyzed in a separate laboratory period and led to important pedagogical opportunities about the absorption and fluorescence of organic compounds. (Contains 2 figures and 3 schemes.)
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Research
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A