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.

Automated summary

F4DNTT and F8DNTT were synthesized through bisthiomethyl alkene intermediates accessible by McMurry coupling or Wittig olefination of partially fluorinated naphthalene precursors. DFT-based calculations, NEXAFS spectroscopy, and UV/Vis measurements were used to analyze the electronic structures of the partially fluorinated DNTTs, revealing reduced exciton binding in thin films.