Abstract
Two novel hydrazine based sensors, BPPIH (N1,N3-bis(perfluorophenyl)isophthalohydrazide) and BPBIH (N1′,N3′-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 pKa 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.
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Acknowledgments
PB is thankful to Prof. Dr Harish Hirani, Director, CSIR-CMERI for his immense support of this work in CSIR-CMERI and to WTI-DST funded GAP-214312 for financial support. ARC is also thankful to Supra institutional research grant for her project fellowship. ARC is thankful to Mr Saikat Das, Project Fellow, CSIR-CMERI for many helpful discussions. AM also likes to acknowledge UGC for her UGC NFSC fellowship.
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Roy Chowdhury, A., Mondal, A., Roy, B.G. et al. Hydrazine functionalized probes for chromogenic and fluorescent ratiometric sensing of pH and F−: experimental and DFT studies. Photochem Photobiol Sci 16, 1654–1663 (2017). https://doi.org/10.1039/c7pp00246g
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DOI: https://doi.org/10.1039/c7pp00246g