Fig. 6. Proposed functionalization mechanism for (6,5) SWNTs.

Aniline derivatives can follow two reaction paths in the presence of KO^tBu and DMSO. Under UV-light irradiation, a radical species is formed that attacks the C–C bonds in circumferential direction, leading to the defect configuration for the E₁₁* emission band (blue line). When the reaction is performed in the dark, deprotonation of the amine group and charge delocalization occurs. A nucleophilic attack on bonds with large π-orbital misalignment creates the defect configuration for the E₁₁*⁻ emission band (red line). Similar reaction paths are expected for phenols, thiophenols, and indoles with different carbanion intermediates. It is noteworthy that the deprotonated aniline species is in equilibrium with its protonated form.