Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 10, Issue 24, Pages 6531-6539Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200400635
Keywords
chirality; helical structures; heterocycles; kinetic resolution; molecular glass; oligothiophenes
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Synthesis of thiophene-based [7]helicenes, which are functionalized for both design of organic chiral glasses with strong chiroptical properties and for further homologation to higher [n]helicenes, is reported. The key synthetic transformations are kinetic resolution of the intermediate diketone and the annelation step forming the center benzene ring by means of an intramolecular McMurry reaction. Based upon X-ray crystallographic determinations of the absolute configurations for (+)enantiomers of the diketone and the [7]helicene, stereochemical correlation between the (R) axial chirality of the diketone and the (M) helical chirality of the [7]helicene is established. One such enantiopure trimethylsilyl-substituted [7]helicene possesses enchanced chiroptical properties and forms a chiral molecular glass.
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