TY - JOUR A1 - Tripp, Matthias W. A1 - Koert, Ulrich T1 - Synthesis of 6,13-difluoropentacene JF - Beilstein Journal of Organic Chemistry PY - 2020/// VL - 16 SP - 2136 EP - 2140 SN - 1860-5397 DO - 10.3762/bjoc.16.181 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.16.181 KW - fluorinated acenes KW - Friedel–Crafts reaction KW - ortho-lithiation KW - synthesis N2 - 6,13-Difluoropentacene was synthesized from 1,4-difluorobenzene. Friedel–Crafts annulation of the latter with phthalic anhydride and subsequent reduction of the anthraquinone gave 1,4-difluoroanthracene. After ortho-lithiation and reaction with phthalic anhydride a carboxylic acid was obtained whose Friedel–Crafts acylation and subsequent reductive removal of the oxygen-functionalities resulted in the formation of the target compound. The HOMO–LUMO gap of 6,13-difluoropentacene was determined via UV–vis spectroscopy and compared to other fluorinated pentacenes. ER -