Dibenzohexacene: Stabilization Through Additional Clar Sextets

• Published in: Chemistry : a European journal Vol. 24; no. 5; pp. 1036 - 1040
• Main Authors: Rüdiger, Elias C., Müller, Matthias, Koser, Silke, Rominger, Frank, Freudenberg, Jan, Bunz, Uwe H. F.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 24.01.2018; Wiley Subscription Services, Inc
• Subjects: acenes; Carrier mobility; Chemistry; Chemistry, Multidisciplinary; clar sextet; Coupling; Current carriers; fluorescence; hexacene; Physical Sciences; Quantum chemistry; Science & Technology; Spectroscopy; Tips; Ultraviolet spectroscopy; UV/Vis spectroscopy; hexacene; FUSED N-HETEROACENE; RINGS; SEMICONDUCTORS; STATE; UV/Vis spectroscopy; clar sextet; SOLUBLE HEXACENES; acenes; TRANSISTORS; HEPTACENE; fluorescence; LARGER ACENES; TETRACENE; PENTACENES
• ISSN: 0947-6539; 1521-3765; 1521-3765
• DOI: 10.1002/chem.201704103

Triphenylene units stabilize hexacenes as dibenzohexacenes. The hexacenes formed by a statistical Yamamoto coupling of dibromobenzene with dibromo‐TIPS‐pentacene or, alternatively, Stille coupling with dimethyldibenzostannole. UV/Vis spectroscopy and quantum chemical calculations show that despite the double benzannulation, the species have hexacene‐type character, as evidenced by their redshifted absorption characteristics. The charge carrier mobility of dibenzohexacene 1 a was determined up to 0.2 cm2/(Vs). Stabilized: Adding Clar Sextets to the end stabilizes a hexacene.