一种基于PET机理pH荧光探针的合成及其性能研究

doi:10.7517/issn.1674-0475.180408

影像科学与光化学 ›› 2018, Vol. 36 ›› Issue (5): 425-433.DOI: 10.7517/issn.1674-0475.180408

一种基于PET机理pH荧光探针的合成及其性能研究

常顺周¹, 相开强², 明伟², 张志忠¹, 田宝柱², 张金龙²

1. 核工业理化工程研究院, 天津 300180;
2. 华东理工大学化学与分子工程学院先进材料与制备教育部重点实验室, 上海 200237

收稿日期:2018-04-20 修回日期:2018-05-16 出版日期:2018-09-15 发布日期:2018-09-15
通讯作者: 田宝柱, 张金龙
基金资助:
国家自然科学基金项目（21573069）和国防科工业局军品配套项目（JPPT-125-4-076）

Synthesis and Properties of a pH Fluorescent Probe Based on PET Mechanism

CHANG Shunzhou¹, XIANG Kaiqiang², MING Wei², ZHANG Zhizhong¹, TIAN Baozhu², ZHANG Jinlong²

1. Research Institute of Physical and Chemical Engineering of Nuclear Industry, Tianjin 300180, P. R. China;
2. Key Laboratory for Advanced Materials, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China

Received:2018-04-20 Revised:2018-05-16 Online:2018-09-15 Published:2018-09-15

摘要/Abstract

摘要： 本文利用光致诱导电子转移（PET）类探针的设计策略，合成了一种以吡喃腈类衍生物为母体、哌嗪为探测基团的新型pH荧光探针DCM-PA。结果表明：DCM-PA的最大吸收波长（λ_abs）和最大荧光发射波长（λ_em）分别为421 nm和590 nm，斯托克斯位移近170 nm。在pH=2~12范围内，DCM-PA的荧光强度随pH的升高而降低，pH=2时的荧光强度是pH=12时荧光强度的12倍；DCM=PA的pKa值为7.2，在pH=6~9范围，荧光强度与pH呈良好的线性关系。对比试验证实DCM-PA实现了pH检测的机理：酸性条件下，哌嗪基团与质子结合削弱了其供电子能力，使DCM-PA荧光增强；碱性条件下，哌嗪通过PET作用使探针荧光猝灭。抗干扰试验表明，DCM-PA在中性酸碱度下对多种阴、阳离子均具有良好的抗干扰能力。

关键词: 荧光探针, pH, 吡喃腈, 光致诱导电子转移

Abstract: A novel pH fluorescent probe (DCM-PA) was synthesized by employing dicyanomethylene-4H-pyran derivative as the fluorophore and piperazine as the response unit. The maximum absorption wavelength(λ_abs) and maximum emission wavelength(λ_em) were tested to be 421 nm and 590 nm, respectively. This means that the stokes shift is near to 170 nm. It was found that the fluorescence intensity gradually increased with the increase of pH value in the pH range of 2-12. The pK_a of DCM-PA was determined to be 7.2. In the range of pH=6-9, there exists a good linear relationship between the fluorescence intensity and pH value. The response mechanism of the pH probe was revealed by the control experiment:Under acidic conditions, the electron donating ability of piperazine group will weaken after combining with proton, leading to the enhancement of the fluorescence intensity. Under alkaline conditions, the fluorescence will be quenched by the photoinduced electron transfer (PET) process. Moreover, it was found that DCM-PA exhibited a good anti-interference ability to different cations and anions.

Key words: fluorescent probe, pH, dicyanomethylene-4H-pyran, photoinduced electron transfer

常顺周, 相开强, 明伟, 张志忠, 田宝柱, 张金龙. 一种基于PET机理pH荧光探针的合成及其性能研究[J]. 影像科学与光化学, 2018, 36(5): 425-433.

CHANG Shunzhou, XIANG Kaiqiang, MING Wei, ZHANG Zhizhong, TIAN Baozhu, ZHANG Jinlong. Synthesis and Properties of a pH Fluorescent Probe Based on PET Mechanism[J]. Imaging Science and Photochemistry, 2018, 36(5): 425-433.

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一种基于PET机理pH荧光探针的合成及其性能研究

Synthesis and Properties of a pH Fluorescent Probe Based on PET Mechanism

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