В журнале European Journal of Organic Chemistry (IF=2,8) опубликована статья c участием сотрудников Института: к.х.н. М.С. Казанцева (снс, зав. лабораторией органической электроники) и д.х.н. Ю.В. Гатилова (внс. Группа рентгеноструктурного анализа):
Aryl-Bridged Thienonaphthalimides: Synthesis, Characterization and Optoelectronic Properties
Prof. Leonid V. Kulik, Dr. Olga L. Krivenko, Danil A. Nevostruev, Elena S. Kobeleva, Natalia V. Kravets, Dr. Mikhail N. Uvarov, Ivan A. Molchanov, Dr. Alexey A. Dmitriev, Dr. Maxim S. Kazantsev, Dr. Yurii V. Gatilov, Dr. Vladimir A. Zinovyev, Dr. Ekaterina A. Zelentsova, Prof. Yuri P. Tsentalovich, Dr. Konstantin M. Degtyarenko, Dr. Denis S. Baranov
EJOC, Volume27, Issue5, February 5, 2024, e202300848
https://doi.org/10.1002/ejoc.202300848
Graphical Abstract
A simple protocol with thienannulation at the last step has been developed for the synthesis of aryl-bridged thienonaphthalimides. This unusual approach has significant advantages, namely, thiophene precursors and organolithium reagents are not used to assemble the π-conjugated molecules. It was found that the aryl-bridged thienonaphthalimides are ambipolar organic semiconductors.
Abstract
Three small molecules consisting of thieno-fused naphthalimide units connected via aromatic linkers were synthesized to study the effect of fused thiophene rings on the properties of naphthalimide-based molecules. A protocol for the synthesis of thienonaphthalimide-based molecules without prior preparation and use of thienonaphthalimide precursors and organoelement compounds (organolithium, organotin, or organoboron compounds) was developed. The protocol is based on double thienannulation of bis-alkyne substrates with sodium sulfide. The thin-film morphology, photophysical and electrochemical properties of the obtained small molecules were studied. Single-layer non-doped organic light-emitting diodes based on fluorene-bridged thienonaphthalimide dimer showed yellow emission with luminance of 2200 cd/m2, and current efficiency of 0.35 cd/A. Combination of transient electroluminescence and photo-CELIV methods allowed to estimate electron and hole mobility in the synthesized compounds; both are in order of 10−6 cm2V−1 s−1.
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