7:8,9:10-Dibenzo-1,2,3,4-tetrafluoro- triphenylene:  Synthesis, Structure, and Photophysical Properties of a Novel [5]Helicene

A simple and efficient synthesis and crystallographic analysis of the partially fluorinated 7:8,9:10-dibenzo-1,2,3,4-tetrafluorotriphenylene, 1, in 59% yield is reported. Compound 1 is a blue luminescent [5]helicene in both solution and the solid state. It spontaneously forms enantiomorphous single...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-06, Vol.70 (13), p.5309-5312
Main Authors: Morrison, Darryl J, Trefz, Tyler K, Piers, Warren E, McDonald, Robert, Parvez, Masood
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Crystallography, X-Ray
Exact sciences and technology
Fluorescent Dyes - analysis
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Molecular Conformation
Molecular Structure
Organic chemistry
Polycyclic Compounds - analysis
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Preparations and properties
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Summary:A simple and efficient synthesis and crystallographic analysis of the partially fluorinated 7:8,9:10-dibenzo-1,2,3,4-tetrafluorotriphenylene, 1, in 59% yield is reported. Compound 1 is a blue luminescent [5]helicene in both solution and the solid state. It spontaneously forms enantiomorphous single crystals from racemic samples and exhibits slipped, face-to-face F···Cπ contacts within the stacks of molecules.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0506231