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  • Title: Arylene ethynylene macrocycles with intramolecular π-π stacking.
    Author: Chen S, Yan Q, Li T, Zhao D.
    Journal: Org Lett; 2010 Nov 05; 12(21):4784-7. PubMed ID: 20873849.
    Abstract:
    Arylene ethynylene macrocycles containing 9,10-anthrylene or 1,4-naphthylene units were synthesized. In chloroform, significant resonance upfield shifting was observed with β-protons of anthrylene and naphthylene in NMR spectra. This was considered to result from partial stacking of these aromatic units intramolecularly, driven by attractive π-π interactions. DFT calculations supported the proposed intramolecular stacking motif. Moreover, a liquid-crystal phase was exhibited by the anthrylene-containing macrocycle, by virtue of the unique discotic shape.
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