Literaturnachweis - Detailanzeige
Autor/inn/en | Petty, Anthony J., II; Odom, Susan A. |
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Titel | Ethynylated Acene Synthesis and Photophysics for an Organic Chemistry Laboratory Course |
Quelle | In: Journal of Chemical Education, 98 (2021) 5, S.1741-1749 (9 Seiten)Infoseite zur Zeitschrift
PDF als Volltext |
Zusatzinformation | ORCID (Petty, Anthony J., II) ORCID (Odom, Susan A.) |
Sprache | englisch |
Dokumenttyp | gedruckt; online; Zeitschriftenaufsatz |
ISSN | 0021-9584 |
DOI | 10.1021/acs.jchemed.0c01360 |
Schlagwörter | Organic Chemistry; Science Laboratories; Undergraduate Students; Laboratory Experiments; Synthesis; Molecular Structure; Spectroscopy |
Abstract | 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. (As Provided). |
Anmerkungen | 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 |
Erfasst von | ERIC (Education Resources Information Center), Washington, DC |
Update | 2022/1/01 |