Science Advances

Supplementary Materials

This PDF file includes:

  • Fig. S1. Full synthetic scheme of 1.
  • Fig. S2. NMR spectra of S2.
  • Fig. S3. NMR spectra of 4b.
  • Fig. S4. 1H NMR (400 MHz) spectra of 5a.
  • Fig. S5. 1H NMR spectra of 5b.
  • Fig. S6. 13C NMR spectra of 5b.
  • Fig. S7. MALDI-TOF mass spectra of C70H20 (1a).
  • Fig. S8. MALDI-TOF mass spectra of C115H70 (1b).
  • Fig. S9. 1H NMR spectrum of the carboncone (1b).
  • Fig. S10. Theoretical simulations for 1H NMR spectra of 1b and the possible heptagon-containing isomer.
  • Fig. S11. 13C NMR spectrum of the carboncone (1b).
  • Fig. S12. Packing mode of 1b in the crystal.
  • Fig. S13. The transition state (TS) structures for cone-to-cone inversion of 1a and 1b.
  • Fig. S14. IRC calculation results of the inversion TS of 1a and 1b.
  • Fig. S15. Structures of compounds 7, 8, 9b, and 10b.
  • Fig. S16. Energy barriers for different ring closure steps on A2 and the relative energies of the intermediate products by a dication pathway.
  • Fig. S17. Energy barriers for different ring closure steps on A3 and the relative energies of the intermediate products by a dication pathway.
  • Fig. S18. Energy barriers for different ring closure steps on A4 and the relative energies of the intermediate products by a dication pathway.
  • Fig. S19. Energy barriers for different ring closure steps on A5 and the relative energies of the intermediate products by a dication pathway.
  • Fig. S20. Energy barriers for different ring closure steps on A6 and the relative energies of the intermediate products by a dication pathway.
  • Fig. S21. Energy barriers for different ring closure steps on A7 and the relative energies of the intermediate products by a dication pathway.
  • Fig. S22. Energy barriers for different ring closure steps on A8 and the relative energies of the intermediate products by a dication pathway.
  • Fig. S23. Energy barriers for different ring closure steps on A3′ and the relative energies of the intermediate products by a dication pathway.
  • Fig. S24. UV-vis absorption spectra of 7 and 8.
  • Fig. S25. Molecular orbitals (from HOMO−1 to LUMO+1) of carboncone 1a and 1b calculated at the B3LYP/6-31G(d,p) level.
  • Fig. S26. Molecular orbitals (from HOMO−1 to LUMO+1) of nanographene 7 calculated at the B3LYP/6-31G(d,p) level.
  • Fig. S27. Molecular orbitals (from HOMO−1 to LUMO+1) of 2 and 8 calculated at the B3LYP/6-31G(d,p) level.
  • Table S1. Crystallographic data and structure refinement details of 1b.
  • Table S2. Cartesian coordinates of optimized species at the B3LYP/6-31G(d,p) level on Gaussian 09.
  • Table S3. UV-vis absorption of 1a predicted by TD-DFT calculations at the B3LYP/6-31G(d,p) level.
  • Table S4. Calculated vibrational frequencies at the B3LYP/6-31G(d,p) level for prominent bands of carboncone 1b in the IR spectrum (in cm−1).

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