Fully Bridged Triphenylamines Comprising Five‐ and Seven‐Membered Rings. Issue 34 (9th May 2022)

• Record Type: Journal Article
• Authors: Michalsky, Ina; Gensch, Viktoria; Walla, Christian; Hoffmann, Marvin; Rominger, Frank; Oeser, Thomas; Tegeder, Petra; Dreuw, Andreas; Kivala, Milan
• Is Part Of: Chemistry. Volume 28:Issue 34(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-05-09
• Subjects: bridged triarylamines -- charge transfer -- co-crystallization -- electron donor -- N-heterocycle; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202200326
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A family of fully bridged triphenylamines with embedded 5‐ and 7‐membered rings is presented. The compounds are potent electron donors capable to undergo donor/acceptor interactions with strong cyano‐based acceptors both in the solid state and solution. These interactions were evaluated by IR and UV/vis spectroscopy as well as X‐ray crystallography. The vinylene‐bridged compound was oxidized to the corresponding 1, 2‐diketone which readily underwent acid‐catalyzed condensation with selected 1, 2‐phenylenediamines. The resulting π‐extended quinoxaline derivatives represent valuable building blocks for the development of functional chromophores upon appropriate functionalization. Abstract : The heptagon makes the difference : A new family of versatile electron donors based on fully bridged triphenylamines with embedded 5‐ and 7‐membered rings has been realized. The structural and optoelectronic properties of the compounds were evaluated both in experiment and theory. The compounds form donor/acceptor systems with strong cyano‐based acceptors and are prone to further functionalization towards π‐extended polycyclic scaffolds.