New β-diketone-boron difluoride based near-infrared fluorescent probes for polarity detection

Abstract

Two new β-diketone-boron difluoride based near-infrared fluorescent probes 1 and 2 which exhibit polarity sensitivity have been designed and synthesized. Probes 1 and 2 are composed of β-diketone-boron difluoride moiety...

A New Deep‐Red to Near‐infrared Emission and Polarity Sensitive Fluorescent Probe Based on β‐Diketone‐boron Difluoride and Coumarin Derivative

“…The spectra was provided in the Supporting Information (Figure S6-S8). Similar with the previous fluorescent probe 1 in our laboratory, [48] CO-DBD also has a "Donor-Acceptor-Donor" long conjugate system (Scheme S2). In addition, compared with our previous probe 1, the new probe CO-DBD replaces the unilateral styrene section with coumarin moiety, which is expected to restrict the rotation and improve the photophysical property.…”

“…Wang and colleagues synthesized series of coumarin‐difluoroboron hybrid dyes for mitochondrial staining [47] . Our group have developed two polarity sensitive fluorescent probes by utilizing β‐diketone‐boron difluoride moiety as an acceptor unit, and a diethylamino group or a phenolic hydroxyl group as donor units [48] . Although these two probes possess favorable polarity sensitivity, the fluorescence quantum yield as well as absorption and emission wavelength could be further tuned.…”

Unsymmetrical boron diketonates containing strong electron-donating groups as mechanochromic fluorescent solids

“…To understand better this phenomenon, quantum yields were also measured in dichloromethane, in which this quenching effect was then observed for all compounds, dropping fluorescence quantum yields below 0.03. Polarity induced fluorescence quenching in BDK compounds was previously observed by Ma et al 51 Surprisingly, in compounds 1a-d this phenomenon does not come along with a fluorescence redshift as absorption and emission spectra in toluene and dichloromethane are perfectly superimposable; no significant solvatochromism was observed. The fluorescence lifetimes were measured in toluene (Table 2) and are generally quite short, even for strongly fluorescent compound 2b (2,1 ns, φF = 0.90).…”

A Solvatochromic Fluorescent Probe for Solvent Polarity Detection Using a Smartphone

“…[23][24][25][26] Several solvent chromotropic fluorescent probes have been developed to explore the solvent polarity, most of which display obvious diversity in spectral intensity and wavelength measurement. [27][28][29][30][31][32][33][34][35][36][37][38][39] The polarities of pure solvent can be determined by comparing the linear relationship between fluorescence emission wavelength or Stokes shift with polarity parameters. [40,41] The RGB (Red, Green, Blue) is an additive color model in which red, green, and blue primary colors of light are added in various ways to produce a specific color.…”

“…Out of the solvent polarity parameter detection methods, fluorescent probe detection has become a promising method because of its ease of operation, high sensitivity, and selectivity [23–26] . Several solvent chromotropic fluorescent probes have been developed to explore the solvent polarity, most of which display obvious diversity in spectral intensity and wavelength measurement [27–39] . The polarities of pure solvent can be determined by comparing the linear relationship between fluorescence emission wavelength or Stokes shift with polarity parameters [40,41] .…”