TY - JOUR

T1 - Aryl-Bridged Thienonaphthalimides: Synthesis, Characterization and Optoelectronic Properties

AU - Kulik, Leonid V.

AU - Krivenko, Olga L.

AU - Nevostruev, Danil A.

AU - Kobeleva, Elena S.

AU - Kravets, Natalia V.

AU - Uvarov, Mikhail N.

AU - Molchanov, Ivan A.

AU - Dmitriev, Alexey A.

AU - Kazantsev, Maxim S.

AU - Gatilov, Yurii V.

AU - Zinovyev, Vladimir A.

AU - Zelentsova, Ekaterina A.

AU - Tsentalovich, Yuri P.

AU - Degtyarenko, Konstantin M.

AU - Baranov, Denis S.

N1 - This work was supported by RSF grant N 23‐73‐00072 (preparation and testing of organic solar cells). The authors would like to acknowledge the Multi‐Access Chemical Service Center SB RAS for characterization of newly synthesized compounds. L.V.K., O.L.K., E.S.K. and D.S.B. acknowledge the state assignment from the Ministry of Science and Higher Education of Russian Federation (project N AAAA‐A21‐121011390038‐1, OLED fabrication and testing). A.A.D. acknowledge the Supercomputer Centre of Novosibirsk State University for computational resources. M.S.K acknowledges the support via State Assignment of Ministry for Science and Higher Education of Russian Federation (FWUE‐2022‐0011, CV measurements).

PY - 2024/2/5

Y1 - 2024/2/5

N2 - 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.

AB - 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.

KW - Fluorescence

KW - Fused-ring systems

KW - Organic electronics

KW - Polycycles

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85181682145&origin=inward&txGid=a4a3cfd123b3b48ab3b7f49236278dff

UR - https://www.mendeley.com/catalogue/bb6025b8-505a-3271-ba7a-b5ec449f2a15/

U2 - 10.1002/ejoc.202300848

DO - 10.1002/ejoc.202300848

M3 - Article

VL - 27

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 5

M1 - e202300848

ER -