AzaBenzannulated perylene diimide multimers as electron acceptors for organic solar cells

Abstract

We present herein a series of AzaBenzannulated PDI (AzaBPDI) multimers, with their synthesis, characterizations and applications as non-fullerene acceptors in bulk-heterojunction organic solar cells. AzaBPDI dimers and trimer were prepared...

Perylene-diimide for organic solar cells: current scenario and prospects in molecular geometric, functionalization, and optoelectronic properties

“…Device performance can be enhanced through solvent engineering by taking advantage of the solubility gap between the donor and acceptor components of the solvent additive and the boiling point (T b ) of the host solvent. A signicant amount of time and effort has been invested in research and development to determine the best way 163,177,[198][199][200] (c) tri-PDl-functionalized NFAs (PDI-trimers) 232,[238][239][240][241] and (d) tetra-PDI-functionalized NFAs (PDI-tetramers). 267,287,288,290,292 This journal is © The Royal Society of Chemistry 2023 to modify the aromatic core to achieve the desired level of enforced stiffness and torsion angle.…”

Synthesis of 1,6/7‐(NO2)2‐Perylenediimide and 1,6/7‐(NH2)2‐Perylenediimide as Regioisomerically Pure Materials**

“…[29][30][31] Moreover, they can be reduced into NH 2 -PDI, a material precursor of AzaBenzannulated PDIs and BisAzaCoroneneDiimides (BACDs), when using (NH 2 ) 2 -PDI) [32][33][34] which both recently showed promising results as organic n-type semiconductors, [35,36] fluorescent probes [37] and NFAs in OSCs. [38] Therefore, the development of synthetic pathways to efficiently prepare regioisomerically pure 1,6/7-(NO 2 ) 2 -PDIs and 1,6/7-(NH 2 ) 2 -PDIs is more relevant than ever. Studies report the use of pure 1,7-(NO 2 ) 2 -PDIs and 1,7-(NH 2 ) 2 -PDIs regioisomers, stating that they were obtained by successive crystallizations.…”

“…Not only they can be engaged in nucleophilic aromatic substitutions, hetero‐annulation reactions with atoms such as oxygen, sulfur, selenium and nitrogen, and their use as electrophile in Pd‐catalysed cross‐coupling reactions has been recently demonstrated [29–31] . Moreover, they can be reduced into NH 2 ‐PDI, a material precursor of AzaBenzannulated PDIs and BisAzaCoroneneDiimides (BACDs), when using (NH 2 ) 2 ‐PDI) [32–34] which both recently showed promising results as organic n‐type semiconductors, [35,36] fluorescent probes [37] and NFAs in OSCs [38] . Therefore, the development of synthetic pathways to efficiently prepare regioisomerically pure 1,6/7‐(NO 2 ) 2 ‐PDIs and 1,6/7‐(NH 2 ) 2 ‐PDIs is more relevant than ever.…”

ortho O-Annulated azabenzannulated perylenediimide and bisazacoronenediimide

“…Our group recently reported their efficient light-driven synthesis 20 and promising applications as semiconductors when heteroannulated, 21 and NFAs in OSCs when multimerized. 22 Herein, we prepared AzaBPDIs and BACDs presenting hydroxy groups in the vicinity of their ortho position. Their ortho O -annulation offers planar electron-deficient materials, showing an increase of fluorescence and a deepening of their LUMO levels.…”