Synthesis and fluorescence emission properties of 1,3,6,8-tetraarylpyrenes

Hu, Jian Yong; Feng, Xing; Tomiyasu, Hirotsugu; Seto, Nobuyuki; Rayhan, Ummey; Elsegood, Mark R.J.; Redshaw, Carl; Yamato, Takehiko

Abstract

Three types of stable pyrene-based highly fluorescence (blue) compounds, 1-, 1,6-bis, 1,8-bis and 1,3,6,8-tetrakis(7-tert-butylpyrenyl)pyrenes and 1,3,6,8-tetrakis[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]pyrene, were successfully synthesized via a Pd/Cu-catalysed Suzuki cross-coupling reaction of the corresponding bromopyrenes with 7-tert-butyl-1-pyrenylboronic ester or 2-[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]-4,4,5,5-tetramethyl[1,3,2] dioxaborolane, respectively. All compounds have good solubility in common organic solvents and high thermal stability with melting points up to 270 °C; the exceptions are the isomeric 1,6-bis-, and 1,8-bispyrenyl-substituted pyrenes. All products show high extinction coefficients of absorption (kmax 349-396 nm) and high quantum yields (kmax 432-465 nm; Uf 0.75-0.99) in dichloromethane solution, and emit strong fluorescence in the visible region ranging from deep-blue to pure-blue on increasing the number of substituents. This data suggests that such systems have promise as blue emitters in organic light-emitting device (OLED) applications (OLED = organic light emitting diode). Crystal structures were determined for 1,3,6,8-tetrakis [9,9-bis(3-methylbutyl) -9H-fluoren-2-yl] pyrene and 1,3,6,8-tetrakis(4-methoxyphenyl)pyrene. © 2013 Elsevier B.V. All rights reserved.

Citation

Hu, J. Y., Feng, X., Tomiyasu, H., Seto, N., Rayhan, U., Elsegood, M. R., …Yamato, T. (2013). Synthesis and fluorescence emission properties of 1,3,6,8-tetraarylpyrenes. Journal of molecular structure, 1047, 194-203. https://doi.org/10.1016/j.molstruc.2013.04.074

• Journal Article Type: Article
• Acceptance Date: Apr 23, 2013
• Online Publication Date: May 11, 2013
• Publication Date: Sep 5, 2013
• Deposit Date: Jun 8, 2022
• Journal: Journal of Molecular Structure
• Print ISSN: 0022-2860
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 1047
• Pages: 194-203
• DOI: https://doi.org/10.1016/j.molstruc.2013.04.074
• Keywords: Pyrene; Suzuki cross-coupling reaction; Tetraarylpyrenes; Tetrafluorenylpyrenes; Fluorescence emission properties
• Public URL: https://hull-repository.worktribe.com/output/3622113