Science Advances

Supplementary Materials

This PDF file includes:

  • Scheme S1. Synthesis of 13+·3PF6.
  • Scheme S2. Synthesis of 23+·3PF6.
  • Scheme S3. Synthesis of 36+·6PF6.
  • Scheme S4. Synthesis of 64+·4PF6.
  • Scheme S5. Synthesis of 83+·3PF6.
  • Scheme S6. Synthesis of 93+·3PF6.
  • Fig. S1. 1H and 13C spectrum of 36+·6PF6.
  • Fig. S2. 1H-1H correlation spectroscopy (500 MHz, D2O, 298 K) spectrum of 36+·6PF6.
  • Fig. S3. Electrospray ionization–HRMS of 36+·6PF6.
  • Fig. S4. 1H and 13C spectrum of 64+·4PF6.
  • Fig. S5. 1H-1H correlation spectroscopy spectrum (500 MHz, D2O, 298 K) of 64+·4PF6.
  • Fig. S6. Electrospray ionization–HRMS of 64+·4PF6.
  • Fig. S7. 1H NMR spectrum (400 MHz, CD3CN, 298 K) of 36+·6PF6 (1.34 mM) upon addition of different amount of anthracene.
  • Fig. S8. 1H NMR spectrum (400 MHz, CD3CN, 298 K) of 36+·6PF6 (1.34 mM) upon addition of different amount of phenanthrene.
  • Fig. S9. 1H NMR spectrum (400 MHz, CD3CN, 298 K) of 36+·6PF6 (1.34 mM) upon addition of different amount of pyrene.
  • Fig. S10. 1H NMR spectrum (400 MHz, CD3CN, 298 K) of 36+·6PF6 (1.34 mM) upon addition of different amount of triphenylene.
  • Fig. S11. 1H NMR spectrum (400 MHz, CD3CN, 298 K) of 36+·6PF6 (1.34 mM) upon addition of different amount of corannulene.
  • Fig. S12. 1H NMR spectrum (400 MHz, CD3CN, 298 K) of the mixture of 76+·3PF6 (1.34 mM) and 6eqiv of corannulene and 76+·3PF6 (1.34 mM).
  • Fig. S13. Plot of the upfield shifts of the resonance of proton e (assigned in fig. S11) of 36+·6PF6.
  • Fig. S14. UV-Vis absorption spectrum of 36+·6PF6 at 0.5 μM in MeCN at 298 K.
  • Fig. S15. UV-Vis absorption spectra of polycyclic aromatic hydrocarbon (PAH) guests, 36+·6PF6, and the corresponding 1:1 complexes in MeCN at 298 K.
  • Fig. S16. Fluorescence spectra of the 36+·6PF6 (1 × 10−3 mM) after addition of different equivalents of PAH guests.
  • Fig. S17. Titration plots (heat rate versus time and heat versus guest/host ratio) obtained from ITC experiments of 36+·6PF6 (0.1 mM, 1.4 ml) with naphthalene (2 mM, 0.4 ml) in CH3CN (298 K).
  • Fig. S18. Titration plots (heat rate versus time and heat versus guest/host ratio) obtained from ITC experiments of 36+·6PF6 (0.1 mM, 1.4 ml) with anthracene (2 mM, 0.4 ml) in CH3CN (298 K).
  • Fig. S19. Titration plots (heat rate versus time and heat versus guest/host ratio) obtained from ITC experiments of 36+·6PF6 (0.1 mM, 1.4 ml) with phenanthrene (2 mM, 0.4 ml) in CH3CN (298 K).
  • Fig. S20. Titration plots (heat rate versus time and heat versus guest/host ratio) obtained from ITC experiments of 36+·6PF6 (0.1 mM, 1.4 ml) with pyrene (2 mM, 0.4 ml) in CH3CN (298 K).
  • Fig. S21. Titration plots (heat rate versus time and heat versus guest/host ratio) obtained from ITC experiments of 36+·6PF6 (0.1 mM, 1.4 ml) with triphenylene (2 mM, 0.4 ml) in CH3CN (298 K).
  • Fig. S22. Titration plots (heat rate versus time and heat versus guest/host ratio) obtained from ITC experiments of 36+·6PF6 (0.1 mM, 1.4 ml) with perylene (2 mM, 0.4 ml) in CH3CN (298 K).
  • Fig. S23. Titration plots (heat rate versus time and heat versus guest/host ratio) obtained from ITC experiments of 36+·6PF6 (0.1 mM, 1.4 ml) with corannulene (2 mM, 0.4 ml) in CH3CN (298 K).
  • Fig. S24. 1H NMR spectra (500 MHz, CD3CN, 298 K) of a 1:100 mixture of anthracene and 4 recorded by heating the mixture at 343 K for a certain amount of time.
  • Fig. S25. 1H NMR spectra (500 MHz, CD3CN, 298 K) of a 1:150 mixture of anthracene and 4 recorded by heating the mixture at 343 K for a certain amount of time.
  • Fig. S26. 1H NMR spectra (500 MHz, CD3CN, 298 K) of a 1:200 mixture of anthracene and 4 recorded by heating the mixture at 343 K for a certain amount of time.
  • Fig. S27. 1H NMR spectra (500 MHz, CD3CN, 298 K) of a 1:1:200 mixture of anthracene, 36+·6PF6, and 4, which were recorded by heating the mixture at 343 K for a specific amount of time.
  • Fig. S28. 1H NMR spectra (500 MHz, CD3CN, 298 K) of a 1:1:1.1:200 mixture of anthracene, 36+·6PF6, pyrene, and 4, which were recorded by heating the mixture at 343 K for a specific amount of time.
  • Fig. S29. Plots of −ln(A/A0) versus reaction time of the Diel-Alder reactions of anthracene and the alkyne 4 in different reaction conditions.
  • Fig. S30. 1H NMR spectra (500 MHz, CD3CN, 298 K) of 36+·6PF6 after irradiating the sample with UV light (λmax = 365 nm) for a special amount of time.
  • Fig. S31. ESI-HRMS of a solution of 36+·6PF6 in MeCN, upon irradiation with UV light (λmax = 365 nm) for 8 hours.
  • Fig. S32. ESI-MS of a solution of 36+·6PF6 in MeCN, upon irradiation with UV light (λmax = 365 nm) for a special amount of time.
  • Fig. S33. 1H NMR spectra (500 MHz, CD3CN, 298 K) of 93+·3PF6 after irradiating the sample with UV light (λmax = 365 nm) for a special amount of time.
  • Fig. S34. ESI-HRMS of a solution of 93+·3PF6 in MeCN, upon irradiation with UV light (λmax = 365 nm) for 8 hours.
  • Fig. S35. ESI-MS of a solution of 93+·3PF6 in MeCN, upon irradiation with UV light (λmax = 365 nm) for a special amount of time.
  • Fig. S36. 1H NMR spectrum (500 MHz, CD3CN, 298 K) of 9a2+·2PF6, which was obtained from the UV light irradiation reaction mixture (used for fig. S33) by means of chromatographic purification.
  • Fig. S37. 1H NMR spectra (500 MHz, CD3CN, 298 K) of the solution containing S3 and S4.
  • Fig. S38. Partial 1H NMR spectra (400 MHz, CD3CN, 298 K) of 73+·3PF6, 64+·4PF6, and 83+·3PF6, before and after UV light irradiation (λmax = 356 nm).
  • Fig. S39. 1H NMR spectra (500 MHz, CD3CN, 298 K) of a complex pyrene ⊂ 36+·6PF6 after the sample was irradiated under UV light (λmax = 365 nm) for a special amount of time.
  • Fig. S40. Partial 1H NMR spectra (400 MHz, CD3CN, 298 K) of 36+·6PF6 under UV light (λmax = 365 nm) in the presence of 1.1 eq. of PAH guests.
  • Fig. S41. Partial 1H NMR spectra of 93+·3PF6 under UV light (λmax = 365 nm) for 12 hours in the presence of different equivalents of pyrene.
  • Fig. S42. Transient absorption spectra of 36+·6PF6 and pyrene ⊂ 36+·6PF6 under UV light excitation.
  • Fig. S43. Different views of the solid-state structure of 36+·6PF6.
  • Fig. S44. Different views of the solid-state structure of anthracene ⊂ 36+·6PF6.
  • Fig. S45. Different views of the solid-state structure of phenanthrene ⊂ 36+·6PF6.
  • Fig. S46. Different views of the solid-state structure of pyrene ⊂ 36+·6PF6.
  • Fig. S47. Different views of the solid-state structure of triphenylene ⊂ 36+·6PF6.
  • Fig. S48. Different views of the solid-state structure of perylene ⊂ 36+·6PF6.
  • Table S1. Ka values and thermodynamic parameters for the 1:1 complexes formed between 36+·6PF6 and PAH guests in MeCN at 25°C.
  • References (2631)

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