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Enantiopure, Monodisperse Alleno‐acetylenic Cyclooligomers: Effect of Symmetry and Conformational Flexibility on the Chiroptical Properties of Carbon‐Rich Compounds
Author(s) -
RiveraFuentes Pablo,
NietoOrtega Belén,
Schweizer W. Bernd,
López Navarrete Juan T.,
Casado Juan,
Diederich François
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100131
Subject(s) - enantiopure drug , dispersity , flexibility (engineering) , chemistry , computational chemistry , stereochemistry , organic chemistry , enantioselective synthesis , mathematics , catalysis , statistics
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.