Organic letters

Synthesis of Acetylenic Cyclophanes via Intramolecular Self-Assembly: Evidence of Perfluorophenyl-Phenyl Quadrupole Interactions in the Solution State

MJ Marsella, ZQ Wang, RJ Reid, K Yoon

Index: Marsella, Michael J.; Wang, Zhi-Qiang; Reid, Rodney J.; Yoon, Kunsang Organic Letters, 2001 , vol. 3, # 6 p. 885 - 887

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Citation Number: 60

Abstract

The alternate coplanar stacking of benzene and hexafluorobenzene in the solid state is a well-known phenomenon attributed to the nearly equal yet opposite quadrupole moments of the two species. 1 Indeed, the prevalence of the aryl−perfluoroaryl (Ar H −Ar F ) solid-state packing motif has established this couple as a reliable supramolecular synthon for use in crystal engineering, as exemplified by the elegant studies of Coates and co-workers. 2,3 Despite ...