Premium
Dibenzohexacene: Stabilization Through Additional Clar Sextets
Author(s) -
Rüdiger Elias C.,
Müller Matthias,
Koser Silke,
Rominger Frank,
Freudenberg Jan,
Bunz Uwe H. F.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704103
Subject(s) - stille reaction , pentacene , quantum chemical , coupling (piping) , chemistry , absorption spectroscopy , triphenylene , computational chemistry , photochemistry , materials science , physics , organic chemistry , polymer , optics , molecule , electrode , metallurgy , thin film transistor
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 cm 2 /(Vs).