Original title:
Preparation and Physicochemical Properties of [6]Helicenes Fluorinated at Terminal Rings.
Authors:
Církva, Vladimír ; Jakubík, Pavel ; Žádný, Jaroslav ; Vacek, J. ; Strašák, Tomáš ; Hrbáč, J. ; Císařová, I. ; Storch, Jan Document type: Papers Conference/Event: Advances in Organic, Bioorganic and Pharmaceutical Chemistry LIBLICE 2018 /53./, Lázně Bělohrad (CZ), 20181102
Year:
2018
Language:
eng Abstract:
Two fluorinated helicenes, tetrafluoro[6]helicene and octafluoro[6]helicene were prepared photochemically and their physicochemical and optical properties were investigated. A separation of racemic tetrafluoro[6]helicene into individual enantiomers (P and M) was performed and the racemization barrier was determined. Crystal structures of major synthetic products including individual enantiomers of tetrafluoro[6]helicene were determined showing the replacement of π-π and CH-π interactions by CH-F interactions with increasing fluorine substitution. DFT calculation were performed to get an insight into the charge distribution and HOMO-LUMO gap.
Keywords:
fluorine; helicene; substitution Project no.: GA17-02578S (CEP) Funding provider: GA ČR Host item entry: Book of Abstracts, ISBN N
Rights: This work is protected under the Copyright Act No. 121/2000 Coll.