Ratiometric sensing of fluoride and acetate anions based on a BODIPY-azaindole platform and its application to living cell imaging

Abstract

A new BODIPY-azaindole based fluorescent sensor 1 was designed and synthesized as a new colorimetric and ratiometric fluorescent chemosensor for fluoride. The binding and sensing abilities of sensor 1 towards various anions were studied by absorption, emission and (1)H NMR titration spectroscopies. The spectral responses of 1 to fluoride in acetonitrile-water were studied: an approximately 69 nm red shift in absorption and ratiometric fluorescent response was observed. The striking light yellow to deep brown color change in ambient light and green to blue emission color change are thought to be due to the deprotonation of the indole moiety of the azaindole fluorophore. From the changes in the absorption, fluorescence, and (1)H NMR titration spectra, proton-transfer mechanisms were deduced. Density function theory and time-dependent density function theory calculations were conducted to rationalize the optical response of the sensor. Results were supported by confocal fluorescence imaging and MTT assay of live cells.

Cell permeable fluorescent colorimetric Schiff base chemoreceptor for detecting F− in aqueous solvent

“…In this regard it is needless to say that development of potential colorimetric fluorescent receptors has A c c e p t e d M a n u s c r i p t innate advantages over receptors which are non colorimetric or non fluorescent in nature [19][20][21][22].…”

Directly Connected AzaBODIPY–BODIPY Dyad: Synthesis, Crystal Structure, and Ground- and Excited-State Interactions

“…In recent past, BF 2 -chelated dipyrromethenes (BODIPYs) [1][2][3][4][5] have drawn major attention because of their broader range of applications as laser dyes, 6-8 fluorescent stains and labels in imaging, [9][10][11][12] indicator dyes in sensors and chemosensors, [13][14][15] photodynamic therapy (PDT) agents, [16][17][18][19] and building light energy converting donor-acceptor systems. [20][21][22][23][24][25][26][27][28] The tremendous potential applications of BODIPY dyes is attributable to their attractive photophysical properties such as narrow absorption and emission bands, high molar absorption coefficients and quantum yields, high solubility in different organic solvents, and low sensitivity to solvent polarity.…”

Highly efficient and selective probes based on polycyclic aromatic hydrocarbons with trimethylsilylethynyl groups for fluoride anion detection

“…Moreover, the response time of the probes attached C C-SiMe 3 substituent is much shorter than those probes with Si-O bonds, which usually exhibits response times in the minutes range . [10,16,[23][24][25][26][27][28][29][30][31][32][33][34][35] …”