generation of more than one EPR-active species. NMR studies with oxidants (Figure ) showed that most of the 1 H NMR signals disappeared with less than 1 equiv. of the oxidant, and no peaks were observed with more than 1.5 equiv. of the oxidant, further indicating that paramagnetic species were generated. As mentioned earlier, atomically precise and structurally uniform N-doped aromatic belts are discrete models of NCNTs. Therefore, stoichiometrically controlled chemical oxidation of 2 and isolation of oxidized species were attempted next. Oxidants with different counter anions and varying oxidant stoichiometry were screened. It was found that the stabilities of the cations were highly dependent on the counter anions. The purple color of the solutions derived from the radical cations disappeared within a short period for BF4 -or PF6 -counter anions, whereas the solutions remained purple for a while in the case of SbF6 -or SbCl6 -. Treatment of 2 with 2 equiv. of AgB(C6F5)4 in dichloromethane and slow diffusion in n-hexane at -30 °C over a period of 1 week resulted in the formation of single crystals of Ndoped nanobelt dication salt 2 2+ •2[B(C6F5)4] -. The thick purple crystals were stable at 0 °C under argon for at least one month. The structure of 2 2+ •2[B(C6F5)4] -was unambiguously determined by X-ray diffraction (Figure ). The space group was monoclinic I2/a. Unlike the neutral compound, where one-sixth of the molecule is an asymmetric unit, half of the molecule is crystallographically independent of the dication compound, and the belt structure contracts uniaxially. To further investigate the electronic nature of 2, density functional theory (DFT) calculations were carried out at the B3LYP/6-31 G (d) level. The calculated optimal structure of 2 (Figure ) matches well with the experimental results obtained by X-ray analysis. Notably, DFT studies revealed that the energies of all orbitals between HOMO and HOMO-5 lie within a narrow range of 0.10 eV (Figure ). Furthermore, the electron density on the HOMO was localized on the pmethoxyphenylamine moieties, while that on the LUMO was localized on the central belt (Figure ). DFT calculations performed on the oxidized species revealed that the optimal structures of 2 n+ in different oxidation states (n = 1-3) were similar (Figure ) and spins were localized on the pmethoxyphenylamine moieties (Figure ). Time-dependent DFT calculations of 2 and the cations also supported the experimental results (Table ). The absorption peak of 2 at 334 nm can be assigned to the HOMO-6 ® LUMO+1 (360.6 nm, f = 0.9802) and In summary, we successfully synthesized a novel class of Ndoped aromatic belts via a six-fold annulative double N-arylation reaction. This new synthetic strategy can expand the scope of accessibility of synthetically difficult belt molecules using the conventional intramolecular contraction pathway. N-doped belt 2 was chemically oxidized, and the generated diradical species 2 2+ •2[B(C6F5)4] -was successfully isolated and characterized. Further studies on the detailed electronic and magnetic properties of 2 n+ are required for their future applications.