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

Ronit Sebastine Bernard; Viktorija Andruleviciene; Oleksandr Bezvikonnyi; Dmytro Volyniuk; Jurate Simokaitiene; Rimantas Henrikas Kublickas; Juozas Vidas Grazulevicius

doi:10.1016/j.jphotochem.2022.113969

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

Ronit Sebastine Bernard
, Viktorija Andruleviciene
, Oleksandr Bezvikonnyi
, Dmytro Volyniuk
, Jurate Simokaitiene
, Rimantas Henrikas Kublickas
, Juozas Vidas Grazulevicius^*

^*Corresponding author for this work

Kaunas University of Technology

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

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.

Original language	English
Article number	113969
Journal	Journal of Photochemistry and Photobiology A: Chemistry
Volume	430
DOIs	https://doi.org/10.1016/j.jphotochem.2022.113969
Publication status	Published - 1 Sept 2022
Externally published	Yes

Keywords

Hole mobility
Inductive effect
Ionization potential
Mesomeric effect
Trifluoromethyl group

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10.1016/j.jphotochem.2022.113969

Cite this

Bernard, R. S., Andruleviciene, V., Bezvikonnyi, O., Volyniuk, D., Simokaitiene, J., Kublickas, R. H., & Grazulevicius, J. V. (2022). Impact of the substitution pattern of the acceptor on the properties of the bis(trifluoromethyl)phenyl disubstituted aromatic diamines. Journal of Photochemistry and Photobiology A: Chemistry, 430, Article 113969. https://doi.org/10.1016/j.jphotochem.2022.113969

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

abstract = "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.",

keywords = "Hole mobility, Inductive effect, Ionization potential, Mesomeric effect, Trifluoromethyl group",

author = "Bernard, \{Ronit Sebastine\} and Viktorija Andruleviciene and Oleksandr Bezvikonnyi and Dmytro Volyniuk and Jurate Simokaitiene and Kublickas, \{Rimantas Henrikas\} and Grazulevicius, \{Juozas Vidas\}",

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doi = "10.1016/j.jphotochem.2022.113969",

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Bernard, RS, Andruleviciene, V, Bezvikonnyi, O, Volyniuk, D, Simokaitiene, J, Kublickas, RH & Grazulevicius, JV 2022, 'Impact of the substitution pattern of the acceptor on the properties of the bis(trifluoromethyl)phenyl disubstituted aromatic diamines', Journal of Photochemistry and Photobiology A: Chemistry, vol. 430, 113969. https://doi.org/10.1016/j.jphotochem.2022.113969

Impact of the substitution pattern of the acceptor on the properties of the bis(trifluoromethyl)phenyl disubstituted aromatic diamines. / Bernard, Ronit Sebastine; Andruleviciene, Viktorija; Bezvikonnyi, Oleksandr et al.
In: Journal of Photochemistry and Photobiology A: Chemistry, Vol. 430, 113969, 01.09.2022.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Impact of the substitution pattern of the acceptor on the properties of the bis(trifluoromethyl)phenyl disubstituted aromatic diamines

AU - Bernard, Ronit Sebastine

AU - Andruleviciene, Viktorija

AU - Bezvikonnyi, Oleksandr

AU - Volyniuk, Dmytro

AU - Simokaitiene, Jurate

AU - Kublickas, Rimantas Henrikas

AU - Grazulevicius, Juozas Vidas

PY - 2022/9/1

Y1 - 2022/9/1

N2 - 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.

AB - 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.

KW - Hole mobility

KW - Inductive effect

KW - Ionization potential

KW - Mesomeric effect

KW - Trifluoromethyl group

UR - https://www.scopus.com/pages/publications/85129524692

U2 - 10.1016/j.jphotochem.2022.113969

DO - 10.1016/j.jphotochem.2022.113969

M3 - Article

AN - SCOPUS:85129524692

SN - 1010-6030

VL - 430

JO - Journal of Photochemistry and Photobiology A: Chemistry

JF - Journal of Photochemistry and Photobiology A: Chemistry

M1 - 113969

ER -

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

Abstract

Keywords

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