Push-pull chromophores by reaction of 2,3,5,6-tetrahalo-1,4-benzoquinones with 4-(N,N-dialkylanilino)acetylenes

Date

2016-03-03

Author

Dengiz, Çağatay
GAWEL, Przemyslaw
TRAPP, Nils
RUHLMANN, Laurent
BOUDON, Corinne
DIEDERICH, Francois

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A series of new push-pull chromophores were synthesized from electron-rich 4-(N,N-dialkylanilino) acetylenes and 2,3,5,6-tetrahalo-1,4-benzoquinones. The reactivity of the latter differs substantially from that of the previously investigated 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The transformation with fluoranil gave orange-colored, bis-donor-substituted chromophores with a tricyclic, cyclobutene-fused dihydrobenzofuranone core. In contrast, the reaction with chioranil yielded mono donor-substituted, blue 1,4-benzoquinone-based chromophores, which were further reacted with tertiary amines to form bis-donor-substituted push-pull systems. The structures of the new chromophores were confirmed by X-ray analysis, and mechanisms for their formation are proposed. They feature intense intramolecular charge-transfer bands in the visible region, and their optoelectronic properties were investigated by UV/Vis spectroscopy, electrochemistry, and computational analysis.

Subject Keywords

Push-pull chromophores, Quinones, Chloranil, Fluoranil, [2+2] Cycloaddition

URI

https://hdl.handle.net/11511/42373

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2016.01.017

Collections

Department of Chemistry, Article

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Citation Formats

Ç. Dengiz, P. GAWEL, N. TRAPP, L. RUHLMANN, C. BOUDON, and F. DIEDERICH, “Push-pull chromophores by reaction of 2,3,5,6-tetrahalo-1,4-benzoquinones with 4-(N,N-dialkylanilino)acetylenes,” TETRAHEDRON, pp. 1213–1224, 2016, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42373.