Fluorescence Enhancement of Pyrene Chromophores Induced by Alkyl Groups through 蟽鈥撓€ Conjugation: Systematic Synthesis of Primary, Secondary, and Tertiary Alkylated Pyrenes at the 1, 3, 6, and 8 Posit

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• 作者：Yosuke Niko ; Susumu Kawauchi ; Shun Otsu ; Katsumi Tokumaru ; Gen-ichi Konishi
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：April 5, 2013
• 年：2013
• 卷：78
• 期：7
• 页码：3196-3207
• 全文大小：608K
• 年卷期：v.78,no.7(April 5, 2013)
• ISSN：1520-6904

文摘

We have systematically synthesized 1-, 3-, 6-, and 8-alkyl-substituted pyrene derivatives using the latest synthesis methods and investigated the effects of alkyl substitution on the photophysical properties of the pyrene chromophore. Like the trimethylsilyl group, which is known to enhance the fluorescence properties of some chromophores through 蟽*鈭捪€* conjugation, alkyl groups (primary, secondary, and tertiary) enhanced the fluorescence quantum yield of the pyrene chromophore through 蟽鈥撓€ conjugation in most cases. While these enhancements in the fluorescence quantum yield were beyond expectations, the results were supported by absolute measurements. These results also indicate that ubiquitous alkyl groups can be used to tune the photophysical properties of the pyrene chromophore, as well as to improve the solubility or prevent aggregation. In other words, they can be used to develop new photofunctional materials.