Development of Tetrameric N-Annulated Perylene Diimides Using "Click" Chemistry.

Autor: Koenig JDB; Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4, Canada., Farahat ME; Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4, Canada., Welch GC; Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4, Canada.
Jazyk: angličtina
Zdroj: ChemSusChem [ChemSusChem] 2022 Jun 08; Vol. 15 (11), pp. e202200492. Date of Electronic Publication: 2022 May 12.
DOI: 10.1002/cssc.202200492
Abstrakt: 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 (sbfNPDI 4 ) was found to have an extended and flexible geometry, while the planar pyrene NPDI tetramer (pyrNPDI 4 ) 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 pyrNPDI 4 than sbfNPDI 4 . 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.
(© 2022 Wiley-VCH GmbH.)
Databáze: MEDLINE
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