N,N-di(4-methoxyphenyl)hydrazones of carbazole and phenothiazine carbaldehydes containing 4-methoxyphenyl groups as hole transporting materials
Type
ArticleAuthors
Durgaryan, RanushSimokaitiene, Jurate
Dabuliene, Asta
Volyniuk, Dmytro
Bezvikonnyi, Oleksandr
Jankauskas, Vygintas
Matulis, Vitaly
Lyakhov, Dmitry

Klymenko, Ivan
Schmaltz, Bruno
Grazulevicius, Juozas Vidas
KAUST Department
Computer, Electrical and Mathematical Science and Engineering Division, 4700 King Abdullah University of Science and Technology, Thuwal 23955–6900, Saudi ArabiaVisual Computing Center (VCC)
Computer, Electrical and Mathematical Science and Engineering (CEMSE) Division
Date
2022-03-21Embargo End Date
2024-03-21Permanent link to this record
http://hdl.handle.net/10754/676308
Metadata
Show full item recordAbstract
In a quest of exploitation of low-cost chemistry for the preparation of hole-transporting materials, we investigated the synthesis of N,N-di(4-methoxyphenyl)hydrazones and the corresponding dihydrazones of carbazole and phenothiazine carbaldehydes. The electron photoemission spectrometry measurements of the layers of the synthesized compounds revealed low ionization potentials in the range of 5.27–5.41 eV. Charge-transporting properties of the compounds were characterized by xerographic time of flight method. The measurements revealed hole mobilities reaching 10−3 cm2/Vs at high electric fields. DFT calculations of the geometry, electronic structure, absorption and photoluminescence spectra of the compounds were carried out to explain and supplement experimental data. The results of calculations show that the first maxima in absorption spectra of the compounds can be attributed to the π-π * local excitation of conjugated system including mainly lone electron pairs of the nitrogen atoms of hydrazone and carbazole or phenothiazine moieties. It is not accompanied by any significant charge transfer. The experimentally observed dramatic effect on the emissive properties of the compounds by attachment of the hydrazone moieties is explained by rotation of para-methoxyphenyl ring into the plane of carbazole moiety upon excitation, which leads to significantly larger charge transfer in the case of S1→S0 emission, compared to S0→S1 absorption.Citation
Durgaryan, R., Simokaitiene, J., Dabuliene, A., Volyniuk, D., Bezvikonnyi, O., Jankauskas, V., Matulis, V., Lyakhov, D., Klymenko, I., Schmaltz, B., & Grazulevicius, J. V. (2022). N,N-di(4-methoxyphenyl)hydrazones of carbazole and phenothiazine carbaldehydes containing 4-methoxyphenyl groups as hole transporting materials. Synthetic Metals, 287, 117057. https://doi.org/10.1016/j.synthmet.2022.117057Sponsors
Funding from the Research Council of Lithuania (LMTLT), Agreement No. [S-LZ-19-2]. All Gaussian16 computations were performed on KAUST's Ibex HPC. The authors thank the KAUST Supercomputing Core Lab team for assistance with execution tasks on Skylake nodes.Publisher
Elsevier BVJournal
Synthetic MetalsAdditional Links
https://linkinghub.elsevier.com/retrieve/pii/S0379677922000510ae974a485f413a2113503eed53cd6c53
10.1016/j.synthmet.2022.117057