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2007
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In the Laboratory
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Making Molecular Borromean Rings
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A Gram-Scale Synthetic Procedure for the Undergraduate Organic Lab
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Cari D. Pentecost, Nicholas Tangchaivang, Stuart J. Cantrill, Kelly S. Chichak, Andrea J. Peters, and J. Fraser Stoddart
Department of Chemistry and Biochemistry and the California NanoSystems Institute, University of California, Los Angeles, CA 90095-1569
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May 2007
Vol. 84 No. 5
p. 855
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| Abstract |
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Borromean rings (BRs) have long fascinated scholars of all disciplines for their wide cultural appeal and unique topology. Undergraduate students are no exception and so we have modified our published experimental procedure for the synthesis of molecular BRs to turn it into a lab instruction experiment suitable for undergraduate students to pursue in an organic chemistry laboratory course. Herein, we describe a procedure that requires seven 4-hour blocks of time to allow an undergraduate student to prepare the molecular BRs on a gram-scale in 90% yield. Just as important as engaging students in the BRs is the fact that the making of the molecular BRs incorporates several important, yet nonetheless overlooked, areas of chemistry. They include synthetic organic, physical organic, inorganic and metallo-organic chemistry, supramolecular, and dynamic covalent chemistry, all packaged up under the same umbrella in one project.
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| Supplement |
The following material for the instructors is available: (i) cost analysis tables providing a spreadsheet of the necessary materials and their current prices; (ii) a spreadsheet with all the ratios entered into one document so that a instructor can determine the quantities of chemicals needed for each class; (iii) a full experimental section containing further details of the synthetic procedures; (iv) suggested test or prelab questions about the BR self-assembly process; and (v) suggested demonstration activities to aid the instructor in describing the BR topology..
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| More Information |
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Citation |
Pentecost, Cari D.; Tangchaivang, Nicholas; Cantrill, Stuart J.; Chichak, Kelly S.; Peters, Andrea J.; Stoddart, J. Fraser. J. Chem. Educ. 2007, 84, 855.
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Keywords |
Aldehydes / Ketones; Amines / Ammonium Compounds; Hands-On Learning / Manipulatives; Laboratory Instruction; Metals; Molecular Recognition; NMR Spectroscopy; Noncovalent Interactions; Organic Chemistry; Synthesis; Upper-Division Undergraduate
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History |
Created:
Last Updated: |
3/22/2007
4/9/2007
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 Caution! | | Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations. |
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