A Macrocyclic Arene Derived from Pagoda[4]arene: Cavity Reshaping, Complexation with Neutral Guests, and CPL Property
Yu-Jie Long1,2, Wei-Chen Guo1,2, Kui-Zhu Song2
1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Abstract:
A new type of macrocyclic arene P4-2D-A was conveniently synthesized by a one-step reaction from pagoda[4]arene. P4-2D-A existed as a fixed conformation with fluorescence emission arising from the π system of the anthracene unit. Moreover, P4-2D-A had a barrel-shaped, electron-rich cavity, as evidenced by electrostatic-potential maps, which enabled it to encapsulate different neutral linear guests in both solution and the solid state. Interestingly, as the alkyl chain lengthened and the terminal group became more electron withdrawing, association constants increased substantially, reflecting the deep cavity and multiple intermolecular interactions provided by P4-2D-A. Furthermore, P4-2D-A displayed stable planar chirality, and chiral HPLC afforded a clean resolution of the enantiomers. They displayed mirror-image CD signals and CPL property, suggesting potential application in chiral luminescent materials.
Related Concept Videos
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Aromatic Hydrocarbon Anions: Structural Overview
Due to the absence of continuous...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)


