Journal
ORGANIC LETTERS
Volume 18, Issue 13, Pages 3054-3057Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01049
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Funding
- Office of Basic Energy Sciences, Office of Science, U.S. Department of Energy [DE-FG02-04ER15514]
- Department of Chemistry, Mississippi State University
- U.S. Department of Energy (DOE) [DE-FG02-04ER15514] Funding Source: U.S. Department of Energy (DOE)
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Bis-corannulenoanthracene (C50H22, 5) was prepared by the Diels-Alder double cycloaddition of isocorannulenofuran with bis-benzyne, followed by deoxygenation of the adducts. Despite the presence of a pentacene core, 5 is stable enough to he isolated and stored. A cycloaddition reaction of 5 with maleic anhydride produces 10 which exhibits strong affinity toward C-60, as evidenced by H-1 NMR titration experiment. Synthesis of 10 demonstrates the synthetic utility of hydrocarbon 5 in the preparation of the barrelene-based molecular clips with two benzocorannulene pincers adorned with polar substituents on their tethers, which will allow for immobilization of the receptors on solid supports.
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