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Synthesis of a Perylene Diimide Dimer with Pyrrolic N–H Bonds and N‐Functionalized Derivatives for Organic Field‐Effect Transistors and Organic Solar Cells
Author(s) -
Vespa Marcus,
Cann Jonathan R.,
Dayneko Sergey V.,
Melville Owen A.,
Hendsbee Arthur D.,
Zou Yingping,
Lessard Benoît H.,
Welch Gregory C.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801055
Subject(s) - diimide , perylene , dimer , chemistry , organic solar cell , solar cell , deprotonation , photochemistry , polymer chemistry , organic chemistry , molecule , polymer , materials science , ion , optoelectronics
This study reports on the new and optimized synthesis of an N‐annulated perylene diimide dimer with functional N–H moieties. The presence of two N–H moieties renders the dimer relatively insoluble in most organic solvents. The dimer is easily functionalized with electron donating hexyl chains or electron withdrawing tert ‐butyloxycarbonyl (tBOC) groups to yield highly soluble materials. The tBOC groups can be thermally cleaved in the thin film to give the parent dimer. The N–H bonds are acidic and interact with volatile organic bases. Deprotonation results in a color change from red to blue. All compounds have utility as electron transport materials in organic field‐effect transistors and green solvent, air processed organic solar cells. Electron mobilities were on the order of about 2–7 × 10 –6 cm 2 /V s. Solar cell power conversion efficiency reached 2 % for those using the tBOC functionalized dimer, 3 % for those using the H‐atom functionalized dimer, and 6 % for those using the hexyl chain functionalized dimer. The performance of the latter is quite impressive considering the simple materials synthesis and greener solar cell processing.