Display options
Cite
Gawel P, Dengiz C, Finke AD, et al. Synthesis of cyano-substituted diaryltetracenes from tetraaryl[3]cumulenes. Angew Chem Int Ed Engl. 2014;53(17):4341-5doi: 10.1002/anie.201402299.
Gawel, P., Dengiz, C., Finke, A. D., Trapp, N., Boudon, C., Gisselbrecht, J. P., & Diederich, F. (2014). Synthesis of cyano-substituted diaryltetracenes from tetraaryl[3]cumulenes. Angewandte Chemie (International ed. in English), 53(17), 4341-5. https://doi.org/10.1002/anie.201402299
Gawel, Przemyslaw, et al. "Synthesis of cyano-substituted diaryltetracenes from tetraaryl[3]cumulenes." Angewandte Chemie (International ed. in English) vol. 53,17 (2014): 4341-5. doi: https://doi.org/10.1002/anie.201402299
Gawel P, Dengiz C, Finke AD, Trapp N, Boudon C, Gisselbrecht JP, Diederich F. Synthesis of cyano-substituted diaryltetracenes from tetraaryl[3]cumulenes. Angew Chem Int Ed Engl. 2014 Apr 22;53(17):4341-5. doi: 10.1002/anie.201402299. Epub 2014 Mar 24. PMID: 24664956.
Copy Download .nbib Format: NLM
Share it on

Angew Chem Int Ed Engl. 2014 Apr 22;53(17):4341-5. doi: 10.1002/anie.201402299. Epub 2014 Mar 24.

Synthesis of cyano-substituted diaryltetracenes from tetraaryl[3]cumulenes.

Angewandte Chemie (International ed. in English)

Przemyslaw Gawel, Cagatay Dengiz, Aaron D Finke, Nils Trapp, Corinne Boudon, Jean-Paul Gisselbrecht, François Diederich

Affiliations

  1. Laboratorium für Organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093 Zürich (Switzerland).

PMID: 24664956 DOI: 10.1002/anie.201402299

Abstract

A versatile, two-step synthesis of highly substituted, cyano-functionalized diaryltetracenes has been developed, starting from easily accessible tetraaryl[3]cumulenes. This unprecedented transformation is initiated by [2+2] cycloaddition of tetracyanoethylene (TCNE) to the proacetylenic central double bond of the cumulenes to give an intermediate zwitterion, which after an electrocyclization cascade and dehydrogenation yields 5,5,11,11-tetracyano-5,11-dihydrotetracenes in a one-pot procedure. A subsequent copper-assisted decyanation/aromatization provided the target 5,11-dicyano-6,12-diaryltetracene derivatives. All of the postulated structures were confirmed by X-ray crystallography. The new chromophores are thermally highly stable and feature promising fluorescence properties for potential use in optoelectronic devices. They are selective chemosensors for Cu(I) ions, which coordinate to one of the CN substituents and form a 1:1 complex with an association constant of Ka =1.5×10(5)  L mol(-1) at 298 K.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: [2+2] cycloaddition; [3]cumulenes; chemosensors; electrocyclization; tetracenes

Publication Types