Donor- and/or Acceptor-Substituted Expanded Radialenes: Theory, Synthesis, and Properties

Ramsaywack S, Karaca S, Gholami M, Murray AH, Hampel F, Mcdonald R, Elmaci N, Luethi HP, Tykwinski R (2014)

Publication Type: Journal article

Publication year: 2014

Journal

Journal of Organic Chemistry American Chemical Society

Book Volume: 79

Pages Range: 10013-10029

Journal Issue: 21

DOI: 10.1021/jo5016085

Abstract

The synthesis of donor- (D) and/or acceptor (A)-expanded [4]radialenes has been developed on the basis of readily available dibromoolefin (7), tetraethynylethene (10 and 20), and vinyl triflate (12) building blocks. The successful formation of D/A radialenes relies especially on (1) effective use of a series alkynyl protecting groups, (2) Sonogashira cross-coupling reactions, and (3) the development of ring closing reactions to form the desired macrocyclic products. The expanded [4]radialene products have been investigated by spectroscopic (UV-vis absorption and emission) and quantum chemical computational methods (density functional theory and time dependent DFT). The combined use of theory and experiment provides a basis to evaluate the extent of D/A interactions via the cross-conjugated radialene framework as well as an interpretation of the origin of D/A interactions at an orbital level.

Authors with CRIS profile

Frank Hampel Lehrstuhl für Organische Chemie I Rik Tykwinski Lehrstuhl für Organische Chemie I

Additional Organisation(s)

Exzellenz-Cluster Engineering of Advanced Materials (EAM)

Involved external institutions

Eidgenössische Technische Hochschule Zürich (ETHZ) / Swiss Federal Institute of Technology in Zurich CH Switzerland (CH) Izmir Institute of Technology (IZTECH) TR Turkey (TR) University of Alberta CA Canada (CA)

How to cite

APA:

Ramsaywack, S., Karaca, S., Gholami, M., Murray, A.H., Hampel, F., Mcdonald, R.,... Tykwinski, R. (2014). Donor- and/or Acceptor-Substituted Expanded Radialenes: Theory, Synthesis, and Properties. Journal of Organic Chemistry, 79(21), 10013-10029. https://doi.org/10.1021/jo5016085

MLA:

Ramsaywack, Sharwatie, et al. "Donor- and/or Acceptor-Substituted Expanded Radialenes: Theory, Synthesis, and Properties." Journal of Organic Chemistry 79.21 (2014): 10013-10029.

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