Hydrazine functionalized probes for chromogenic and fluorescent ratiometric sensing of pH and F−: experimental and DFT studies,Photochemical & Photobiological Sciences

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Hydrazine functionalized probes for chromogenic and fluorescent ratiometric sensing of pH and F−: experimental and DFT studies
Photochemical & Photobiological Sciences ( IF 2.7 ) Pub Date : 2017-09-28 00:00:00 , DOI: 10.1039/c7pp00246g
Additi Roy Chowdhury _{1,

2,

3,

4,

5} , Amita Mondal _{1,

2,

3,

4,

6} , Biswajit Gopal Roy _{4,

6,

7,

8} , Jagadeesh C. Bose K _{4,

9,

10,

11} , Sudit Mukhopadhyay _{4,

9,

10,

11} , Priyabrata Banerjee _{1,

2,

3,

4,

5}

Affiliation

Two novel hydrazine based sensors, BPPIH (N¹,N³-bis(perfluorophenyl)isophthalohydrazide) and BPBIH (N^1′,N^3′-bis(perfluorobenzylidene)isophthalohydrazide), are presented here. BPPIH is found to be a highly sensitive pH sensor in the pH range 5.0 to 10.0 in a DMSO–water solvent mixture with a pK_a value of 9.22. Interesting optical responses have been observed for BPPIH in the above mentioned pH range. BPBIH on the other hand turns out to be a less effective pH sensor in the above mentioned pH range. The increase in fluorescence intensity at a lower pH for BPPIH was explained by using density functional theory. The ability of BPPIH to monitor the pH changes inside cancer cells is a useful application of the sensor as a functional material. In addition fluoride (F⁻) selectivity studies of these two chemosensors have been performed and show that between them, BPBIH shows greater selectivity towards F⁻. The interaction energy calculated from the DFT-D3 supports the experimental findings. The pH sensor (BPPIH) can be further interfaced with suitable circuitry interfaced with desired programming for ease of access and enhancement of practical applications.

中文翻译：

肼官能化的探针用于pH和F的发色和荧光比率传感^-：实验和研究DFT

两种新型肼基传感器，BPPIH（Ñ ¹，Ñ ³ -双（全氟苯基）isophthalohydrazide）和BPBIH（Ñ ^1'，Ñ ^3' -双（perfluorobenzylidene）isophthalohydrazide），在此提出。BPPIH被发现是在pH范围5.0一个高度敏感的pH传感器对在DMSO-水溶剂混合物与AP 10.0 ķ_一个的9.22值。在上述pH范围内，对于BPPIH观察到了有趣的光学响应。BPBIH另一方面，在上述pH范围内，pH传感器的效果较差。使用密度泛函理论解释了BPPIH在较低pH值下荧光强度的增加。BPPIH监测癌细胞内pH值变化的能力是传感器作为功能材料的有用应用。在氟除了（F ^-已执行这两种化学传感器的选择性研究，并表明它们之间）BPBIH对F显示更大的选择性^-。从DFT-D3计算出的相互作用能支持了实验结果。pH传感器（BPPIH可以进一步与合适的电路接口，该合适的电路与期望的编程接口，以便于访问和增强实际应用。

更新日期：2017-11-08

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