Soluble and Planar 2,9-Diazaperopyrenes through Reductive Aromatization of Perylene Diimides: Tunable Emission and Aggregation Behaviors.

Reductive aromatization of perylene diimides with acid anhydrides in the presence of Mn or Zn metals provides soluble and planar 2,9-diazaperopyrenes with ester groups at 1,3,8,10-positions. The pivaloxy groups at the peripheral positions can be transformed into a variety of aryl groups through nickel-catalyzed cross-coupling of ester groups. Emission colors of diazaperopyrenes are tunable by the peripheral substituents. The peripheral substituents also affect the aggregation behaviors of 2,9-diazaperopyrenes in the solution and solid states.

The reductive aromatization of naphthalene diimide: a versatile platform for 2,7-diazapyrenes.

The reductive aromatization of naphthalene diimide provides tetrapivaloxy-2,7-diazapyrene, which serves as a versatile platform toward peripherally substituted 2,7-diazapyrenes. Time-resolved microwave conductivity measurements demonstrated that the intrinsic electron mobility of 2,7-diazapyrene is significantly higher than that of the corresponding pyrene.

Selective α-arylation of α,ß-unsaturated imides mediated by a visible light photoredox catalyst.

Visible light-mediated α-arylation of α,ß-unsaturated imides is achieved via aminium radicals generated from diarylalkylamines using a photoredox catalyst. On the basis of emission quenching experiments, a plausible pathway of the reaction is discussed.