Synthesis of Alkynylated Benzo[a]naphtho[2, 3‐i]phenazine Derivatives. Issue 3 (11th December 2015)

• Record Type: Journal Article
• Authors: Hahn, Sebastian; Biegger, Philipp; Bender, Markus; Rominger, Frank; Bunz, Uwe H. F.
• Is Part Of: Chemistry. Volume 22:Issue 3(2016)
• Page Start: 869
• Page End: 873
• Publication Date: 2015-12-11
• Subjects: acenes -- arenes -- condensation -- N-heterocycles -- organic electronics; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201503856
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Thermal condensation of 2, 3‐diamino‐1, 4‐(bistriisopropylsilylethynyl)benzene, ‐naphthalene, ‐anthracene, and ‐benzothiadiazole substrates with 1, 2‐naphthalenedione forms bent benzophenazine‐type heteroarenes in a one‐step reaction in good to excellent yields. The targets are investigated by UV/Vis spectroscopy, cyclic voltammetry, and single‐crystal X‐ray crystallography. The packing of the targets in the solid state follows either a herringbone or a brick wall motif. In the case of 8, 13‐bis(triisopropylsilylethynyl)dibenzo[ a, i ]phenazine, polymorphs with either packing result. Abstract : Acene from a condensation : Four different bent benzo[ a ]naphtho[2, 3‐ i ]phenazines are efficiently synthesized by condensation of aromatic diamines with 1, 2‐naphthalenedione. The resultant azaacenes are spectroscopically and crystallographically characterized. Optical properties are studied and compared with those of the isomeric linear azaacenes.