Development of Tetrameric N‐Annulated Perylene Diimides Using “Click” Chemistry

• Published in: ChemSusChem 2022-06, Vol.15 (11), p.e202200492-n/a
• Main Authors: Koenig, Josh D. B., Farahat, Mahmoud E., Welch, Gregory C.
• Format: Article
• Language: English
• Subjects: Acceptor materials; Alkynes; Chemical synthesis; click chemistry; Cycloaddition; Diimide; Energy conversion efficiency; N-annulated perylene diimide; non-fullerene acceptor; Optoelectronics; organic photovoltaics; Photovoltaic cells; tetramer
• ISSN: 1864-5631; 1864-564X
• DOI: 10.1002/cssc.202200492

Herein, we report the design, synthesis, and characterization of two novel N‐annulated perylene diimide (NPDI) tetramer arrays that were developed using copper catalyzed alkyne‐azide cycloaddition. Despite the optoelectronic properties of both tetramers being nearly identical, the two tetramers exhibited very different molecular geometries. The twisted spirobifluorene NPDI tetramer (sbfNPDI4) was found to have an extended and flexible geometry, while the planar pyrene NPDI tetramer (pyrNPDI4) exhibited a highly congested and conformationally locked geometry. Organic photovoltaic devices were constructed to demonstrate the use of both new compounds as electron acceptor materials, where slightly higher power conversion efficiencies were achieved with pyrNPDI4 than sbfNPDI4. This study highlights the viability of using “click” chemistry as a facile synthetic strategy towards the development of new multicomponent perylene diimide materials for organic electronic applications. Central core influences geometry: Two novel N‐annulated perylene diimide tetramers were synthesized using facile “Click” chemistry, where the central core influenced intramolecular geometry. The utility of both compounds as functional organic electronic materials was demonstrated using organic photovoltaic devices.