ABSTRACT
A general and efficient synthetic methodology for the preparation of enantio- and diastereopure [6]-, and [7]helicenes is developed. Commercially available chiral binaphthanols are utilized to generate the arylene-vinylene precursors, which undergo helical folding via photocyclization to give enantio- and diastereopure [6]-, and [7]helicenes. These optically pure helicenes could be easily obtained via silica gel column chromatography without the use of expensive HPLC or chiral resolution reagents. The configurations and structures of these helicenes are confirmed by CD spectra and X-ray crystallographic analysis. This work provides a new method for preparation of enantiopure helicenes.
ABSTRACT
Axial chiral bisbenzocoumarins were synthesized for the first time by converting naphthanol units in 1,1'-binaphthol (BINOL) molecule to the benzocoumarin rings. The substitute groups on 3,3'-positions of bisbenzocoumarins showed significant influence on their aggregation-induced emission enhancement (AEE) properties. It was also found that BBzC1 with ester groups on 3,3'-positions exhibit an abnormal aggregation-annihilation circular dichroism (AACD) phenomenon, which could be caused by the decrease of the dihedral angle between adjacent benzocoumarin rings in the aggregation state. The single crystal structure of BBzC1 showed that the large dihedral angle in molecule prohibited the strong π-π stacking interactions, which could be main factors for its AEE properties.
