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Versatile Bottom-up Approach to Stapled π-Conjugated Helical Scaffolds: Synthesis and Chiroptical Properties of Cyclic o-Phenylene Ethynylene Oligomers


  • This work was supported by the Junta de Andalucía (P09-FQM-04571), MINECO (CTQ2011-22455, CTQ2011-24783), and Comunidad de Madrid and European Social Fund (SOLGEMAC-S2009/ENE-1617). We thank CSIRC-UGR and “Centro de Computación Científica-UAM” for computation time. The project “Factoría de Cristalización, CONSOLIDER INGENIO-2010” and the beamline I19 at Diamond (UK) provided X-ray structural facilities for this work. DChL, NF, LMF, and AML thank CSD2006-00015, UGR, and MEC for funding.


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Spring loaded: The smallest members of a family of carbon nanocoils (CNCs), adopting a fixed helical structure, have been synthesized by introduction of one or two staples in o-phenylene ethynylene oligomers. The chiroptical responses of the systems having enantiopure L-tartrate-derived staples confirmed the induced helicity. Theoretical studies suggest that these CNCs are pseudoelastic.