Impact of the substitution pattern of the acceptor on the properties of the bis(trifluoromethyl)phenyl disubstituted aromatic diamines

• Published in: Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2022-09, Vol.430, p.113969, Article 113969
• Main Authors: Bernard, Ronit Sebastine, Andruleviciene, Viktorija, Bezvikonnyi, Oleksandr, Volyniuk, Dmytro, Simokaitiene, Jurate, Kublickas, Rimantas Henrikas, Grazulevicius, Juozas Vidas
• Format: Article
• Language: English
• Subjects: Hole mobility; Inductive effect; Ionization potential; Mesomeric effect; Trifluoromethyl group
• ISSN: 1010-6030; 1873-2666
• DOI: 10.1016/j.jphotochem.2022.113969

[Display omitted] •New aromatic diamines containing 2,5- or 3,5-bis(trifluoromethyl)benzene moieties were investigated.•Mesomeric effect was detected for the compounds with 2,5-bis(trifluoromethyl)benzene moieties.•2,5-Bis(trifluoromethyl)benzene based compounds demonstrated lower ionization potential values and enhanced hole mobilities. New aromatic diamines with bis(trifluoromethyl)phenyl substituents were synthesized and investigated. Theoretical and experimental results revealed that compounds containing 2,5-bis(trifluoromethyl)benzene moiety exhibit interplay between inductive and mesomeric effects opening new possibilities in the field of organic optoelectronics. Furthermore, the CF3 group at ortho position leads to the closer packing of molecules in the single crystal as well as in the amorphous state. As a result, CF3 group decreases the ionization potential and enhance the hole mobilities of the synthesized compounds containing 2,5-bis(trifluoromethyl)benzene moieties as compared to their counterparts containing 3,5-bis(trifluoromethyl)benzene moieties.