Synthesis and derivatization of expanded [n]radialenes (n=3, 4)

Gholami M, Ramsaywack S, Chaur MN, Murray AH, Mcdonald R, Ferguson MJ, Echegoyen L, Tykwinski R (2013)

Publication Type: Journal article, Original article

Publication year: 2013

Journal

Chemistry - A European Journal Wiley-VCH Verlag

Original Authors: Gholami M., Ramsaywack S., Chaur M.N., Murray A.H., McDonald R., Ferguson M.J., Echegoyen L., Tykwinski R.R.

Publisher: Wiley-VCH Verlag

Book Volume: 19

Pages Range: 15120-15132

Journal Issue: 45

DOI: 10.1002/chem.201302452

Abstract

Versatile, iterative synthetic protocols to form expanded [n]radialenes have been developed (n=3 and 4), which allow for a variety of groups to be placed around the periphery of the macrocyclic framework. The successful use of the Sonogashira cross-coupling reaction to complete the final ring closure demonstrates the ability of this reaction to tolerate significant ring strain while producing moderate to excellent product yields. The resulting radialenes show good stability under normal laboratory conditions in spite of their strained, cyclic structures. The physical and electronic characteristics of the macrocycles have been documented by UV-visible spectroscopy, electrochemical methods, and X-ray crystallography (four derivatives), and these studies provide insight into the properties of these compounds as a function of pendent substitution in terms of conjugation and donor/acceptor functionalization. Feeling the strain: By using a handful of versatile building blocks, expanded radialenes are easily assembled through Sonogashira cross-coupling reactions. X-ray crystallography shows expanded [3]radialenes have a rather significantly strained enyne framework, whereas those of the expanded [4]radialenes show much less strain (see figure). © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Authors with CRIS profile

Rik Tykwinski Lehrstuhl für Organische Chemie I

Additional Organisation(s)

Exzellenz-Cluster Engineering of Advanced Materials (EAM)

Involved external institutions

The University of Texas at El Paso US United States (USA) (US) University of Alberta CA Canada (CA) University of Valle / Universidad del Valle (Univalle) CO Colombia (CO)

How to cite

APA:

Gholami, M., Ramsaywack, S., Chaur, M.N., Murray, A.H., Mcdonald, R., Ferguson, M.J.,... Tykwinski, R. (2013). Synthesis and derivatization of expanded [n]radialenes (n=3, 4). Chemistry - A European Journal, 19(45), 15120-15132. https://doi.org/10.1002/chem.201302452

MLA:

Gholami, Mojtaba, et al. "Synthesis and derivatization of expanded [n]radialenes (n=3, 4)." Chemistry - A European Journal 19.45 (2013): 15120-15132.

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