Synthesis and Molecular Properties of Partially Fluorinated DNTTs

1,2,3,4-Tetrafluoro-dinaphthothienothiophene (F4DNTT) and 1,2,3,4,8,9,10,11-octafluoro-dinaphthothienothiophene (F8DNTT) were synthesized via bisthiomethyl alkene intermediates which were accessible by McMurry coupling or Wittig olefination of partially fluorinated naphthalene precursors. DFT-based electronic structure calculations, near-edge X-ray absorption fine structure (NEXAFS) spectroscopy, and UV/Vis measurements were used for HOMO/LUMO gap determination and to analyze the electronic structures of the partially fluorinated DNTTs. Reduced exciton binding was observed in thin films.