Pyromellitic Diimide-Extended Pillar[6]arene: Synthesis, Structure, and Its Complexation with Polycyclic Aromatic Hydrocarbons

Abstract

A novel pyromellitic diimide-extended pillar[6]­arene was synthesized in two steps with moderate yield for the first time. It showed a symmetrical stretched hexagon structure and could form 1:2 complexes with polycyclic aromatic hydrocarbons in solution. Interestingly, a linear supramolecular array between complex 1@G4 2 and pyrene through π···π stacking interactions was also observed in the solid state.

Naphthalimide-based conjugated macrocycles possessing tunable self-assembly and supramolecular binding behaviours

“…This may be due to the distorted geometry of NP3a / NP3b which is not suitable for binding with planar molecules. By a mole ratio plot based on chemical shift data, a 1:1 stoichiometry was confirmed for NP2a/NP2b and pyrene ( Zeng et al, 2022 ). Through non-linear fitting, the binding constants of NP2a/NP2b with pyrene are 327.43 and 253.33 M −1 respectively.…”

Recent advances in the synthesis and applications of macrocyclic arenes

“…40a). 91 Intermediate 92 was first obtained by the reaction of 1,2,4,5-benzenetetra-carboxylicanhydride with 2,5-dimethoxybenzylamine. Then, 93 was synthesized in 35% yield by the [2+2] cyclization of 92 with paraformaldehyde in the presence of BF 3 ·OEt 2 as the catalyst in DCM.…”

A Benzothiadiazole-Based Self-Assembled Cage for Cadmium Detection

“…We questioned whether the intense fluorescence of the benzothiadiazole-based cage would increase compared to the monomers. Herein, as a continuation of our interest for supramolecular chemistry [ 45 , 46 , 47 , 48 , 49 ], we report a turn-on fluorescent probe based on a self-assembled cage for the selective detection of Cd 2+ . The self-assembled cage 1 was obtained by the condensation of 4,4′-(benzothiadiazole-4,7-diyl)dibenzaldehyde and TREN in chloroform via the [3 + 2] approach ( Scheme 1 ).…”