Synthesis, structures, and conformational characteristics of pillararene-based Diels–Alder adducts with embedded chiral centres

Abstract

[4 + 2] Diels–Alder cycloadditions between quinone-containing pillar[n]arene derivatives and linear dienes lead to distorted conformations and additional chiral centres on the macrocyclic scaffold.

Stereoselective Single Step Cyclization to Give Belt-Functionalized Pillar[6]arenes

“…In contrast to the frequent reports of rim-functionalized pillar­[ n ]­arenes, there have only been a handful of reports of functionalization at the aromatic ring – or belt positions (also described as the “lateral” positions). – Notably, introduction of functional groups at the methylene carbon atoms induces chirality in the pillar­[ n ]­arenes and in the case of functionalization at multiple belt positions results in mixtures of configurational isomers (arising from the fact that each belt substituent can be cis or trans to the adjacent substituent). The reported belt functionalizations have all involved P5 and have either involved initial bromination or lithiation of the belt CH 2 groups.…”

Fluorescence-enhanced supra-amphiphiles based on pillar[5]arene: construction, controllable self-assembly and application in cell imaging

“…[22][23][24][25][26][27] Owing to the significant efforts of scientists, numerous stimuli-responsive host-guest recognition motifs of pillar [5]arenes have been constructed and further utilized in the production of various materials, including pillar [5]arene-based supramolecular polymers and supramolecular amphiphiles. [28][29][30][31][32] In stark contrast, only a limited number of attempts have been made to investigate fluorescence properties of pillar [5]arene-based host-guest systems. 11,12 To advance the application of pillar [5]arene in SFMs (especially supramolecular materials displaying red and NIR emissions), we present here supramolecular assemblies with enhanced red fluorescence through pillar [5]arene-based host-guest recognition (Scheme 1).…”