Ratiometric fluorescence chemodosimeters for fluoride anion based on pyrene excimer/monomer transformation

Abstract

Two pyrene dimers containing an -O-Si-Si-O- or -O-Si-O- linkage have been designed which exhibit ratiometric excimer/monomer emission upon fluoride anion induced Si-O bond cleavage. Incorporation of the probe into water soluble polymeric nanoparticles enhances its intracellular uptake and displays ratiometric fluorescent sensing for F(-) in living cells.

Sensing mechanism for a fluoride chemosensor: invalidity of excited-state proton transfer mechanism

“…This type of chemosensor shows good ratiometric response, arising from the combination of the fluoride-triggered Si-O cleavage with different sensing mechanisms, such as intramolecular charge transfer (ICT), [9][10][11][12][13] excited state proton transfer (ESPT), 14 and excimer-monomer formation. 15 Ratiometric fluorescent chemosensor can circumvent the effects of various interference factors, such as solvent polarity, pH, and temperature. 16 Moreover, this type of fluorescent chemosensor has been successfully operated in aqueous solution and living matrices to detect fluoride anions.…”

Intramolecular charge transfer and sensing mechanism for a colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

“…Among these chemosensors, ratiometric chemosensors with intrinsic advantages of taking the intensity ratio at two different absorption or emission wavelengths [6] can circumvent the effects of various interference factors, such as polarity, probe molecule concentration, photo-illumination and the microenvironment around the probe molecule [11]. Up to now, a plenty of ratiometric chemosensors for fluoride anion have been developed with supposed sensing mechanisms.…”

“…In recent years, a number of chemosensors for fluoride anion have been developed [1][2][3][4][5][6][7] due to the considerable significant role of fluoride to health, environment and industrial processes [8][9][10]. Among these chemosensors, ratiometric chemosensors with intrinsic advantages of taking the intensity ratio at two different absorption or emission wavelengths [6] can circumvent the effects of various interference factors, such as polarity, probe molecule concentration, photo-illumination and the microenvironment around the probe molecule [11].…”

“…Among these chemosensors, those with tert-butyldimethylsilyl and tert-butyldiphenylsilyl belong to the reaction-based type [2] and exhibit higher selectivity and stability. The good ratiometric response of this sort of chemosensor can be ascribed to the fluoride-triggered Si-O cleavage reaction and intramolecular charge transfer (ICT) [1-3, 18, 19] or the excited-state proton transfer (ESPT) [20] or the excimer/ monomer formation [6]. The photophysical properties and geometries of these chemosensors can be inferred from the measured 1 H NMR spectra, time-resolved absorption spectra and fluorescence spectra in the study of the Si-O bond cleavage, ICT and ESPT processes [2,13].…”

Polymeric nanoparticles for optical sensing

“…The innovation behind this nanosystem lies in the exploitation of morphological changes that occur on the cell surface, indicative of various disease states. In another example, pyrene dimers having -O-Si-O-or -O-Si-Si-O-linkages were synthesized and exhibited different excimer/monomer emission due to the presence of fluoride anions (Gai et al, 2012). In particular, pyrene dimers showed characteristic excimer emission (broad peak around 470-480 nm) together with a weak monomer emission (two sharp peaks at 378 and 396 nm).…”