Regioselective Oxidative Oligomerization of 2-Tert-Butylpyrene Toward Structurally Defined Oligomers and Their Application in Organic Light-Emitting Diodes

Year: 2026

Authors: Mia MJ., Tauchi D., Mizoe M., Hashimoto T., Hasegawa M., Chihara H., Iwano H., Yagi S., Fusi M., Mazzeo G., Longhi G., Abbate S., Wang QY., Nakano T., Sugiura K.

Autors Affiliation: Tokyo Metropolitan Univ, Dept Chem, Tokyo, Japan; Kitasato Univ, Dept Chem, Kanagawa, Japan; Osaka Metropolitan Univ, Dept Appl Chem, Osaka, Japan; Univ Brescia, Dept Mol & Translat Med DMMT, Brescia, Italy; CNR, Ist Nazl Ott INO, Res Unit Brescia, Brescia, Italy; Hokkaido Univ, Inst Catalysis ICAT, Sapporo, Hokkaido, Japan; Hokkaido Univ, Grad Sch Chem Sci & Engn, Sapporo, Hokkaido, Japan; Huaibei Normal Univ, Sch Chem & Chem Engn, Huaibei 235000, Peoples R China.

Abstract: By introducing a tert-butyl group at the 2-position of pyrene-a standard compound in photochemistry-we successfully synthesized structurally well-defined oligomeric molecules. The synthesis was achieved via oxidative coupling of 2-tert-butylpyrene using a divalent copper salt, and the resulting oligomer mixture was separated by gel permeation chromatography. The isolated dimer served as a starting material for further coupling reactions, enabling the synthesis of tetramers (4-mers), hexamers (6-mers), octamers (8-mers), and decamers (10-mers). Similarly, the trimer yielded 6-mers and 9-mers, while the 4-mer afforded both 8-mers and 12-mers upon recoupling. Structural analysis of the dimer was carried out using X-ray crystallography, which revealed its detailed 3D structure. For higher-order oligomers, structural evaluation was performed using computational chemistry methods. Furthermore, we investigated the photophysical and electrochemical properties of each isolated oligomer. Notably, we fabricated organic light-emitting diodes using the dimer and the tetramer, obtaining devices that exhibited deep blue electroluminescence with high luminance.

Journal/Review: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

More Information: This work was supported by CREST (Grant Number JPMJCR2001 to KiS, DT, MH, and SY) from the Japan Science and Technology Agency, by the Core-to-Core Program (Grant Number JPJSCCA20250005) from the Japan Society for the Promotion of Science, and by the Research Center for Computational Science, Okazaki (25-IMS-C281,26-IMS-C371).
KeyWords: circularly polarized luminescence; enantiomer separation; organic light-emitting diode; pyrene; regioselective oligomerization
DOI: 10.1002/ejoc.70768