Azaisoquinolinones: N Positions Tell You Different Stories in Their Optical Properties

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• 作者：Junbo Li ; Junkuo Gao ; Gang Li ; Weiwei Xiong ; Qichun Zhang
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：December 20, 2013
• 年：2013
• 卷：78
• 期：24
• 页码：12760-12768
• 全文大小：611K
• 年卷期：v.78,no.24(December 20, 2013)
• ISSN：1520-6904

文摘

Since isoquinolinones and their derivatives have been demonstrated to be powerful building blocks in constructing larger acenes and twistacenes, azaisoquinolinones and their analogues could also be important intermediates to approach larger N-heteroacenes. In this paper, we are interested in developing a concise method to synthesize novel azaisoquinolinones building blocks and studying their physical properties. Our results showed that the different N positions have a large effect on the optical and electrochemical properties of azaisoquinolinones. For example, protonation of 6- and 7-azaisoquinolinones shows different shifts of UV鈥搗is and FL spectra. More interestingly, 6- and 7-azaisoquinolinones exhibited different interactions with metal ions in CH₃CN solution. Upon the addition of 2 equiv of Fe³⁺, 6-azaisoquinolinone displayed an absorption wavelength red-shifted from 470 to 540 nm (螖位 = 70 nm) with a color change from yellow to red, while the interaction between Fe³⁺ and 7-azaisoquinolinone was very weak and there was no obvious color change (螖位 = 18 nm). Moreover, theoretical calculations confirmed the different optical properties with 6- and 7-azaisoquinolinones.