Synthesis and fluorescence emission properties of 1,3,6,8-tetraarylpyrenes
详细信息 查看全文
- 作者：Jian-Yong Hu ; Xing Feng ; Hirotsugu Tomiyasu ; Nobuyuki Seto ; Ummey Rayhan ; Mark R.J. Elsegood ; Carl Redshaw ; Takehiko Yamato
- 关键词：Pyrene ; Suzuki cross-coupling reaction ; Tetraarylpyrenes ; Tetrafluorenylpyrenes ; Fluorescence emission properties
- 刊名：Journal of Molecular Structure
- 出版年：2013
- 出版时间：5 September, 2013
- 年：2013
- 卷：1047
- 期：Complete
- 页码：194-203
- 全文大小：1677 K
文摘
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 ¡ãC; the exceptions are the isomeric 1,6-bis-, and 1,8-bispyrenyl-substituted pyrenes. All products show high extinction coefficients of absorption (¦Ëmax ¡Ö 349-396 nm) and high quantum yields (¦Ëmax ¡Ö 432-465 nm; ¦µf ¡Ö 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.