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Synthesis and Molecular Properties of Partially Fluorinated DNTTs **
Author(s) -
Tripp Matthias W.,
Bischof Daniel,
Dreher Maximilian,
Witte Gregor,
Koert Ulrich
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001635
Subject(s) - chemistry , xanes , naphthalene , homo/lumo , alkene , electronic structure , absorption spectroscopy , absorption (acoustics) , wittig reaction , ultraviolet visible spectroscopy , spectroscopy , exciton , photochemistry , computational chemistry , crystallography , stereochemistry , molecule , organic chemistry , materials science , catalysis , physics , quantum mechanics , composite material
1,2,3,4‐Tetrafluoro‐dinaphthothienothiophene (F 4 DNTT) and 1,2,3,4,8,9,10,11‐octafluoro‐dinaphthothienothiophene (F 8 DNTT) 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.