Triphenylamine pyridine acetonitrile fluorogens with green emission for pH sensing and application in cells

doi:10.1016/j.cclet.2014.11.029

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Abstract

In this work, triphenylamine pyridine acetonitrile compounds PyA1, PyA2 and PyA3 are designed and synthesized. They show green fluorescence in water and bright emission in solid state. They have large Strokes shift (about 100 nm). The excitation and emission spectra are investigated in ethyl acetate, chloroform, cyclohexane, ethanol, water, acetonitrile, THF, DMF and DMSO. It is interesting to find that these compounds are able to sense increasing pH values ranging from pH 2 to 7 by showing different color and emission intensities: almost no emission at pH 2 and strong green emission at pH 7. The acid-base switched color and fluorescence changes can be observed under UV irradiation, in water solution and 1% agarose gel. These changes can be repeated for several cycles. We are able to employ these compounds for cell pH environment imaging.

Key words： Light-emitting materials Solvatochromism TICT effect pH environment Cell imaging

Received: 19 June 2014 Published: 24 November 2014

Fund:

Thisworkwas supported by theNational Basic Research Program of China (973 Program) (Nos. 2012CB720600, 2012CB720603), the National Science Foundation of China (Nos. 91213302, 81373256, 21272181), the National Grand Program on Key Infectious Disease (No. 2012ZX10003002-014), the Program for Changjiang Scholars and Innovative Research Team in University ([62_TD$DIFFF]IF$DTD8_[5]No. IRT1030), and by the Fundamental Research Funds for the Central Universities.

Corresponding Authors: Xiang Zhou E-mail: xzhou@whu.edu.cn

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http://www.chinchemlett.com.cn/EN/10.1016/j.cclet.2014.11.029 OR http://www.chinchemlett.com.cn/EN/Y2015/V26/I03/323

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