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., Redshaw, C., & 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