Fine Tuning of Emission Behavior, Self-Assembly, Anion Sensing, and Mitochondria Targeting of Pyridinium-Functionalized Tetraphenylethene by Alkyl Chain Engineering,ACS Applied Materials & Interfaces

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Fine Tuning of Emission Behavior, Self-Assembly, Anion Sensing, and Mitochondria Targeting of Pyridinium-Functionalized Tetraphenylethene by Alkyl Chain Engineering
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2018-06-25 00:00:00 , DOI: 10.1021/acsami.8b04113
Nan Li ₁ , Yan Yan Liu ₁ , Yan Li ₁ , Jia Bao Zhuang ₁ , Rong Rong Cui ₁ , Qian Gong ₁ , Na Zhao ₁ , Ben Zhong Tang ₂

Affiliation

Compared to the many studies that focus on the development of novel molecular frameworks pertaining to functionalized fluorescent materials, there is lesser emphasis on side chains even though they have a significant impact on the properties and applications of fluorescent materials. In this study, a series of pyridinium-functionalized tetraphenylethene salts (TPEPy-1 to TPEPy-4) possessing different alkyl chains are synthesized, and the influence of chain length on their optical performance and applications is thoroughly investigated. By changing the alkyl chain, the fluorogens exhibit opposite emission behavior in aqueous media because of their distinct hydrophobic nature, and their solid-state emission can be fine-tuned from green to red owing to their distinct molecular configuration. In addition, by increasing the chain length, the microstructure of the self-assembled fluorogens converts from microplates to microrods with various emission colors. Moreover, TPEPy-1 exhibits dual-mode fluorescence “turn-on” response toward NO₃^– and ClO₄^– in aqueous media because the anions induce the self-assembly of fluorogens. Furthermore, the fluorogens display cellular uptake selectivity while the proper alkyl chain impels the fluorogens to penetrate the cell membrane and accumulate in the mitochondria with high specificity.

中文翻译：

通过烷基链工程技术对吡啶官能化的四苯乙烯的发射行为，自组装，阴离子传感和线粒体靶向进行微调

与许多专注于开发与功能化荧光材料有关的新型分子框架的研究相比，侧链的侧重点更少，即使它们对荧光材料的性能和应用产生了重大影响。在这项研究中，合成了一系列具有不同烷基链的吡啶鎓官能化的四苯基乙烯盐（TPEPy-1至TPEPy-4），并彻底研究了链长对其光学性能和应用的影响。通过改变烷基链，由于其独特的疏水性，氟在水性介质中表现出相反的发射行为，并且由于其独特的分子结构，其固态发射可从绿色微调为红色。另外，通过增加链长，自组装氟的微观结构从微孔板转变为具有各种发射颜色的微棒。此外，TPEPy-1对NO表现出双模荧光“开启”响应₃^–和ClO ₄^–在水性介质中，因为阴离子会诱导氟的自组装。此外，氟显示出细胞摄取选择性，而适当的烷基链则促使氟穿透细胞膜并以高特异性积聚在线粒体中。

更新日期：2018-06-25

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