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ERIC Number: EJ1301200
Record Type: Journal
Publication Date: 2021-May
Pages: 9
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
Ethynylated Acene Synthesis and Photophysics for an Organic Chemistry Laboratory Course
Petty, Anthony J., II; Odom, Susan A.
Journal of Chemical Education, v98 n5 p1741-1749 May 2021
An operationally simple, reliable synthesis of ethynylated acenes suitable for an upper-division undergraduate organic chemistry laboratory course has been developed. This experiment requires students to synthesize two acene derivatives and can be completed in 6-8 laboratory sessions (3 h each); a shorter experiment could be realized in the synthesis of only one product. Synthesis is carried out by first treating a terminal alkyne with n-butyllithium in an oven-dried flask under nitrogen at 0°C. An acene quinone is added, which produces a doubly ethynylated diol. Dehydration with SnCl[subscript 2]/HCl yields a bis­(ethynylated) acene, which is purified via a short pad or column of silica gel. The intense colors of the products allow for great ease in determining reaction completion and following the products in chromatography. UV-vis and fluorescence spectroscopy may be used to better understand the effect of molecular structure on electronic properties.
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 - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A