Arylene ethynylene macrocycles with intramolecular π-π stacking.
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.
Chen
Shusen
S
Beijing National Laboratory for Molecular Sciences, Department of Applied Chemistry, College of Chemistry, Peking University, Beijing 100871, China.
Yan
Qifan
Q
Li
Tian
T
Zhao
Dahui
D
D000480:Alkynes / Q000737:chemistry*; D050866:Liquid Crystals; D047028:Macrocyclic Compounds / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
D000480:Alkynes; D047028:Macrocyclic Compounds