Enantiopure, monodisperse alleno-acetylenic cyclooligomers: effect of symmetry and conformational flexibility on the chiroptical properties of carbon-rich compounds.

A series of enantiopure, monodisperse alleno-acetylenic cyclooligomers were synthesized. The single-crystal X-ray structures of the cyclic trimer and hexamer were resolved, providing insights into the symmetry of these molecules. Electronic circular dichroism (ECD), optical rotatory dispersion (ORD), Raman spectroscopy, and vibrational circular dichroism (VCD) data were analyzed with the aid of theoretical calculations. This multidimensional approach ultimately provided general guidelines that are useful for designing carbon-rich compounds with intense chiroptical properties.

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