Influence of thiophene rings on the properties of phenanthro[9,10-d]imidazole derivatives for light-emitting applications
Abstract
Thiophene and its derivatives are extremely popular building blocks for many organic structures used in organic electronics and photovoltaics. However, will the use of thiophene rings as substituents in phenanthro [9,10-d]imidazole derivatives modify their properties so effectively that they become efficient emitters? To answer this question, we obtained a series of phenanthro [9,10-d]imidazole derivatives with thiophene rings at the C2 position. Thermal studies of the obtained derivatives showed that all of them exhibited thermal stability above 200°C. Reduction occurred at the core of the molecule, with a potential below -2 V. During oxidation, strong resonance stabilization of the oxidized species and positive charge dispersion across all aromatic rings were observed. The absorption spectral bands can be attributed to the π→π* transition of phenanthro [9,10-d]imidazole. The emission spectral bands are characterized by a local excited state (LE) transition. Finally, selected derivatives were tested as emitters in OLEDs and LECs. OLEDs showed average maximum EQEs up to 1.6% for 4 and produced deep-blue emission for 3, close to the Broadcast Television Service 2020 standard. In contrast, LECs fabricated with compounds 5 and 6 showed weaker emission but a strong red-shift of the electroluminescence to 596 and 560 nm.
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BibTeX
@article{krawiec2026influence,
title = {{Influence of thiophene rings on the properties of phenanthro[9,10-d]imidazole derivatives for light-emitting applications}},
author = {Agnieszka Krawiec and Nathan Béghin and Michał Filapek and Claudia Wilfinger and Lionel Rechignat and Karol Erfurt and Cyrille Monnereau and Clement Cabanetos and Maxime Rémond and Slawomir Kula},
journal = {Journal of Photochemistry and Photobiology A: Chemistry},
year = {2026},
month = nov,
doi = {10.1016/j.jphotochem.2026.117812},
url = {https://hal.science/hal-05848114v1},
note = {CC BY-NC-ND 4.0},
}
RIS
TY - JOUR
TI - Influence of thiophene rings on the properties of phenanthro[9,10-d]imidazole derivatives for light-emitting applications
AU - Agnieszka Krawiec
AU - Nathan Béghin
AU - Michał Filapek
AU - Claudia Wilfinger
AU - Lionel Rechignat
AU - Karol Erfurt
AU - Cyrille Monnereau
AU - Clement Cabanetos
AU - Maxime Rémond
AU - Slawomir Kula
PY - 2026
DA - 2026/11/02
JO - Journal of Photochemistry and Photobiology A: Chemistry
DO - 10.1016/j.jphotochem.2026.117812
UR - https://hal.science/hal-05848114v1
AB - Thiophene and its derivatives are extremely popular building blocks for many organic structures used in organic electronics and photovoltaics. However, will the use of thiophene rings as substituents in phenanthro [9,10-d]imidazole derivatives modify their properties so effectively that they become efficient emitters? To answer this question, we obtained a series of phenanthro [9,10-d]imidazole derivatives with thiophene rings at the C2 position. Thermal studies of the obtained derivatives showed that all of them exhibited thermal stability above 200°C. Reduction occurred at the core of the molecule, with a potential below -2 V. During oxidation, strong resonance stabilization of the oxidized species and positive charge dispersion across all aromatic rings were observed. The absorption spectral bands can be attributed to the π→π* transition of phenanthro [9,10-d]imidazole. The emission spectral bands are characterized by a local excited state (LE) transition. Finally, selected derivatives were tested as emitters in OLEDs and LECs. OLEDs showed average maximum EQEs up to 1.6% for 4 and produced deep-blue emission for 3, close to the Broadcast Television Service 2020 standard. In contrast, LECs fabricated with compounds 5 and 6 showed weaker emission but a strong red-shift of the electroluminescence to 596 and 560 nm.
SN - 1010-6030
ER -