"Bis-corannulenoanthracene: An Angularly Fused Pentacene as a Precursor" by K G. Kumarasinghe, Frank R. Fronczek et al.

Faculty Publications

Title

Bis-corannulenoanthracene: An Angularly Fused Pentacene as a Precursor for Barrelene-Tethered Receptors for Fullerenes

Authors

K G. Kumarasinghe, Department of Chemistry, Mississippi State University , Mississippi State, Mississippi 39762, United States.
Frank R. Fronczek, Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Henry U. Valle, Department of Chemistry, Mississippi State University , Mississippi State, Mississippi 39762, United States.
Andrzej Sygula, Department of Chemistry, Mississippi State University , Mississippi State, Mississippi 39762, United States.

Document Type

Article

Publication Date

7-1-2016

Abstract

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 be isolated and stored. A cycloaddition reaction of 5 with maleic anhydride produces 10 which exhibits strong affinity toward C60, as evidenced by (1)H 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.

Publication Source (Journal or Book title)

Organic letters

First Page

3054

Last Page

Recommended Citation

Kumarasinghe, K. G., Fronczek, F. R., Valle, H. U., & Sygula, A. (2016). Bis-corannulenoanthracene: An Angularly Fused Pentacene as a Precursor for Barrelene-Tethered Receptors for Fullerenes. Organic letters, 18 (13), 3054-7. https://doi.org/10.1021/acs.orglett.6b01049

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