(Aza)Pentacenes Clipped into a Ring: Stabilization of Large (Aza)Acenes

Lukas Ahrens; Olena Tverskoy; Svenja Weigold; Michael Ganschow; Frank Rominger; Jan Freudenberg; Uwe H F Bunz

doi:10.1002/anie.202015348

(Aza)Pentacenes Clipped into a Ring: Stabilization of Large (Aza)Acenes

Angew Chem Int Ed Engl. 2021 Apr 19;60(17):9270-9273. doi: 10.1002/anie.202015348. Epub 2021 Feb 3.

Authors

Lukas Ahrens¹, Olena Tverskoy¹, Svenja Weigold¹, Michael Ganschow¹, Frank Rominger¹, Jan Freudenberg¹, Uwe H F Bunz^{1

2}

Affiliations

¹ Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
² Centre for Advanced Materials, Im Neuenheimer Feld 225, 69120, Heidelberg, Germany.

Abstract

A doubly alkylene bridged 6,13-diphenylpentacene and analogously bridged azapentacenes were prepared; they are persistent. The doubly bridged azapentacenes display superior photochemical, oxidative and thermal stabilities compared to azapentacenes protected by bis(TIPS-ethynyl)-substituents-clipping an azaacene into a large ring is a viable complement in stabilization.

Keywords: X-ray diffraction; acenes; organic materials; semiconductors; stabilization.

Abstract

Grants and funding