We have prepared and characterized chiral and gated baskets (P/M)-2, each containing a twisted P or M platform and three amidopyridine gates at the rim. Racemic (P/M)-2 was found (¹H NMR and IR spectroscopy) to stay monomeric in CDCl₃ at 298.0 K with the gates forming a seam of intramolecular N–H···N hydrogen bonds. In particular, the amidopyridine gates assume a unidirectional orientation, as directed by the twisted platform, that is, the P-shaped cup sets the amidopyridine gates in a counterclockwise (–) orientation of intramolecular N–H···N hydrogen bonds (VT ¹H/¹³C NMR and M06-2X/6-31G*). The folded form of spacious (355 ų) and chiral (P/M)-2 undergoes an unfolding process in the presence of the polar [D₆]DMSO solvent; specifically, with around 25 vol.-% of [D₆]DMSO, the N–H···N hydrogen bonds at the rim are broken, thereby allowing a stochastic rotation of the amidopyridine gates about the rim. Interestingly, the thermal stability of folded (P/M)-2 is good with only a small fraction of unfolded state(s) forming at 104 °C in o-xylene.

A preparative procedure for obtaining a pair of twisted molecular baskets, each comprising a chiral framework with either right ((P)-1_syn) or left ((M)-1_syn) sense of twist and six ester groups at the rim has been developed and optimized. The racemic (P/M)-1_syn can be obtained in three synthetic steps from accessible starting materials. The resolution of (P/M)-1_syn is accomplished by its transesterification with (1R,2S,5R)-(−)-menthol in the presence of a Ti^IV catalyst to give diastereomeric 8^P and 8^M. It was found that dendritic-like cavitands 8^P and 8^M, in CD₂Cl₂, undergo self-inclusion (¹H NMR spectroscopy) with a menthol moiety occupying the cavity of each host. Importantly, the degree of inclusion of the menthol group was (¹H NMR spectroscopy) found to be greater in the case of 8^P than 8^M. Accordingly, it is suggested that different folding characteristic of 8^P and 8^M ought to affect the physicochemical characteristics of the hosts to permit their effective separation by column chromatography. The absolute configuration of 8^P/8^M, encompassing right- and left-handed “cups”, was determined with the exciton chirality method and also verified in silico (DFT: B3LYP/TZVP). Finally, the twisted baskets are strongly fluorescent due to three naphthalene chromophores, having a high fluorescence quantum yield within the rigid framework of 8^P/8^M.