ERIC Number: EJ1002726
Record Type: Journal
Publication Date: 2012-Sep
Pages: 4
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
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.)
Descriptors: Science Experiments, Organic Chemistry, Laboratories, Undergraduate Study, College Science, Science Instruction, Spectroscopy
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: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Research
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A