Fig. 5

Complexation properties of TQ via plane-to-plane and edge-to-plane non-covalent π-interactions. a–f Expanded ¹H NMR spectra (DMSO-d₆) of TQ•TFA 10 (a), TQ•TFA 10 and coronene (5:1) (b), TQ•TFA 10 and [12]CPP (5:1) (c), TQ•TFA 10, [12]CPP, and coronene (5:1:5) (d), coronene (e), and [12]CPP (f). For b–d, the optimised structures of the corresponding complexes, calculated at the B3LYP-D3/6-31G(d,p) level of theory, are shown as either space-filling (vDW) or ball-and-stick models together with supportive data from the ESI-TOF MS analysis. For b and c, the association constants were determined by NMR titration. g–k Expanded ¹H NMR spectra (DMSO-d₆) of DQ-Im•TFA 9 (g), DQ-Im•TFA 9 and [12]CPP (5:1) (h), [12]CPP (i), 2-hydroxyethyl-TQ•TFA 12 and [12]CPP (5:1) (j), and 2-hydroxyethyl-TQ•TFA 12 (k). No discernible spectral changes were observed in the case of DQ-Im•TFA, 2-hydroxyethyl-TQ•TFA 12, and [12]CPP, indicating the absence of complexation. *The mass number corresponds to the monocation [16–H]⁺