Design, synthesis, and properties of N-annulated perylene-embedded carbon nanorings

Abstract

We report the facile synthesis of two novel carbon nanorings based on N-annulated perylene (NP-[n]CPP, n = 9,10) by Pd-catalyzed Suzuki coupling and a subsequent reductive aromatization reaction. Their photophysical properties were investigated by steady-state and time-resolved spectroscopies. Conjugated NP-[n]CPP nanorings showed a significant redshift (90 nm for emission) compared to the N-annulated perylene unit. In addition, the supramolecular interaction behavior between NP-[10]CPP and fullerene C₆₀ was also studied, and the binding constant was determined to be 1.18 × 10⁵ M⁻¹. Furthermore, the potential application of NP-[9]CPP and NP-[10]CPP in organic field-effect transistors (OFETs) was investigated. Their carrier mobilities were 2.0 × 10⁻⁵ cm² V⁻¹ s⁻¹ and 3.4 × 10⁻⁵ cm² V⁻¹ s⁻¹, respectively.