“Butterfly Wings” Stabilize Heptacene

• Published in: Chemistry : a European journal Vol. 24; no. 32; pp. 8087 - 8091
• Main Authors: Müller, Matthias, Rüdiger, Elias C., Koser, Silke, Tverskoy, Olena, Rominger, Frank, Hinkel, Felix, Freudenberg, Jan, Bunz, Uwe H. F.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 07.06.2018; Wiley Subscription Services, Inc
• Subjects: acenes; Chemistry; Chemistry, Multidisciplinary; heptacenes; Physical Sciences; pi extension; Science & Technology; stabilization through benzannulation; X-ray diffraction; acenes; CONJUGATED HYDROCARBONS; stabilization through benzannulation; RINGS; pi extension; X-ray diffraction; PENTACENE; heptacenes; SOLID-STATE; large acene stabilization through benzannulation heptacene pi-extension X-ray
• ISSN: 0947-6539; 1521-3765; 1521-3765
• DOI: 10.1002/chem.201801079

The synthesis of bisalkynylated derivatives of tetrabenzo[a,c,p,r]heptacene and tetrabenzo[a,c,l,n]pentacene via two‐/fourfold Stille reactions involving a 9‐stannafluorene and suitable tetrabromoacenes is reported. These triphenylene‐“winged” heptacenes are surprisingly stable and maintain a significant portion of the electronic properties of heptacenes. One wing equals half a ring: π‐Extension of tetrabromopentacenes with phenanthrenyl‐“wings” gave stable heptacenes with the optical and electronic characteristics of a linear hexacene.