Hydrazine functionalized probes for chromogenic and fluorescent ratiometric sensing of pH and F−: experimental and DFT studies. Issue 11 (28th September 2017)

• Record Type: Journal Article
• Authors: Roy Chowdhury, Additi; Mondal, Amita; Roy, Biswajit Gopal; K, Jagadeesh C. Bose; Mukhopadhyay, Sudit; Banerjee, Priyabrata
• Is Part Of: Photochemical & photobiological sciences. Volume 16:Issue 11(2017)
• Page Start: 1654
• Page End: 1663
• Publication Date: 2017-09-28
• Subjects: Photochemistry -- Periodicals; Photobiology -- Periodicals; 541.35
• DOI: 10.1039/c7pp00246g
• Languages: English
• ISSNs: 1474-905X

Abstract

Abstract : Two novel hydrazine based sensors, BPPIH ( N 1, N 3 -bis(perfluorophenyl)isophthalohydrazide) andBPBIH ( N 1′, N 3′ -bis(perfluorobenzylidene)isophthalohydrazide), are presented here. Abstract : Two novel hydrazine based sensors, BPPIH ( N 1, N 3 -bis(perfluorophenyl)isophthalohydrazide) andBPBIH ( 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 p K a value of 9.22. Interesting optical responses have been observed forBPPIH 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 forBPPIH was explained by using density functional theory. The ability ofBPPIH 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.