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Synthesis and Characterization of Axially Chiral Molecules Containing Dendritic Substituents
Author(s) -
Peerlings H. W. I.,
Meijer E. W.
Publication year - 1998
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/(sici)1099-0690(199804)1998:4<573::aid-ejoc573>3.0.co;2-n
Subject(s) - dendrimer , axial symmetry , chemistry , steric effects , molecule , stereochemistry , core (optical fiber) , crystallography , polymer chemistry , organic chemistry , materials science , composite material , geometry , mathematics
Enantiomerically pure, axially chiral ( S )‐1,1′‐bi‐2‐naphthol has been used as a core material to which Fréchet‐type dendritic wedges of the zeroth up to the fourth generation were attached, yielding the first axially chiral dendrimers 1−5 . The chiroptical features of these compounds were studied and revealed an increasing molar optical activity for higher generations of dendrimers. This effect can be explained by a larger torsional angle between the naphthyl units, caused by steric repulsions between the dendritic wedges. However, the effect is marginal, indicating a high degree of flexibility present in the axially chiral dendrimers.