New fluorescent pH probes for acid conditions

Zhang, Xuan; Jing, Shiyao; Huang, Shuya; Zhou, Xinming; Bai, Jie-Ming; Zhao, Bao‐Xiang

doi:10.1016/j.snb.2014.09.107

Cited by 61 publications

(20 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Inspired by the previous work, herein we present a coumarin-rhodamine FRET system as a ratiometric pH probe (RC1). Compared with other probes we reported, RC1 possesses ratiometric properties 16,26,29,30,57 and simpler structure 18 and the emission spectrums of coumarin and rhodamine are well separated. Furthermore, RC1 responds to pH fluctuations within a wider pH range (4.20-6.00), 17 so the probe has greater potential for biological application.…”

Section: Introductionmentioning

confidence: 80%

A ratiometric lysosomal pH probe based on the coumarin–rhodamine FRET system

Zhang

Shen

et al. 2015

RSC Adv.

Self Cite

View full text Add to dashboard Cite

The ratiometric pH probe RC1 was constructed by integrating coumarin moiety as FRET donor into rhodamine moiety as FRET acceptor. The probe with a pKa of 4.98 could detect pH in the range of 4.20-6.00 and selectively stain lysosome. a In this study, we developed a coumarin-rhodamine based fluorescence resonance energy transfer (FRET) system RC1 as a ratiometric pH probe. The probe with a pKa of 4.98 was constructed by integrating coumarin moiety as an FRET donor with rhodamine moiety as an FRET accepter. Upon addition of H + , the coumarin emission at 477 nm decreased and the rhodamine emission at 582 nm increased simultaneously. The fluorescence intensity ratio (I477/I582) displayed excellent pHdependent performance and responded linearly to minor pH changes in the range of 4.20-6.00. The probe exhibited brilliant selectivity among different amino acids, metal cations and the ATP. Moreover, it has been successfully applied in fluorescence imaging in HeLa cells and the results indicated that the probe could selectively stain lysosome with low cytotoxicity and excellent photostability. We also applied RC1 to monitor intracellular pH variations induced by dexamethasone. Therefore, RC1 could act as a practical tool for the detection of pH in weakly acidic conditions and provide essential information in medicinal analysis and real biological systems.

show abstract

Section: Introductionmentioning

confidence: 80%

A ratiometric lysosomal pH probe based on the coumarin–rhodamine FRET system

Zhang

Shen

et al. 2015

RSC Adv.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Considering the presence of basic nitrogen and sulfur atoms in 1 , the addition of acids is expected to trigger changes in its photophysical properties . However, only minimal changes were observed after the addition of a large excess of triflic acid (TfOH).…”

Section: Methodsmentioning

confidence: 99%

“…Considering the presence of basic nitrogen and sulfur atoms in 1,t he addition of acids is expected to trigger changes in its photophysical properties. [17] However, only minimal changes were observed after the addition of al arge excess of triflic acid (TfOH). Therefore, we have designed and synthesized as eries of 5-N-arylaminothiazoles (2-6)w ith 4-pyridyl groups at the 2position, which act as strong Lewis basic sites, and investigated the acid-induced changes of their photophysical properties.…”

mentioning

confidence: 99%

Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid

et al. 2016

View full text Add to dashboard Cite

Solutions of 5‐N‐arylaminothiazoles containing pyridyl groups exhibited clear halochromism and halofluorism upon addition of Brønsted and Lewis acids. The addition of triflic acid to solutions of 5‐N‐arylaminothiazoles in Et2O induced bathochromic shifts of the absorption and emission bands. DFT calculations suggested that the spectral changes arise from the protonation of the pyridyl group of the thiazoles in Et2O. Single‐crystal X‐ray diffraction analysis of a thiazole and its protonated form revealed the change of the conformation around the thiazole ring. The emission of white light was accomplished from a single fluorescent dye by adjusting the ratio of dye and B(C6F5)3, whereby the International Commission on Illumination coordinates showed a linear change from blue to orange.

show abstract

“…Amongst the numerous heterocyclic organic luminescent materials, pyrazoline and its derivatives have received increasing attention due to their excellent electro-optical properties [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 ] and wide range of applications. For example, they are used in fluorescent probes, organic light-emitting diodes, and many other materials [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 ]. Generally, pyrazoline and its derivatives display strong emission in dilute solutions, but their emission efficiencies can dramatically decrease in the solid state (e.g., in high concentration in solution, in the aggregated state, as a powder, film, or single crystal) due to strong intramolecular and/or intermolecular interactions between neighboring molecules.…”

Section: Introductionmentioning

confidence: 99%

High Solid Fluorescence of a Pyrazoline Derivative through Hydrogen Bonding

et al. 2017

View full text Add to dashboard Cite

Pyrazoline and its derivatives often exhibit strong emissions in dilute solutions, but their emission intensity is often dramatically reduced in the solid state due to strong intermolecular interactions between neighboring molecules. In this report, we successfully synthesized a new pyrazoline 4-(3-(4-(decyloxy)phenyl)-1-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-5-yl)-N,N-diethylaniline (PPDPD), into which seven fluorine (F) atoms were incorporated. In the solid state, PPDPD emits a strong blue light at λmax 430 nm with a fluorescence quantum yield of up to 41.3%. Single-crystal analysis showed the presence of intra/intermolecular C-H···F bonds that may impede molecular motion and block the non-radiative decay channel. Compound PPDPD therefore shows high emission efficiency in the solid state.

show abstract

New fluorescent pH probes for acid conditions

Cited by 61 publications

References 34 publications

A ratiometric lysosomal pH probe based on the coumarin–rhodamine FRET system

A ratiometric lysosomal pH probe based on the coumarin–rhodamine FRET system

Acid‐Responsive Absorption and Emission of 5‐N‐Arylaminothiazoles: Emission of White Light from a Single Fluorescent Dye and a Lewis Acid

High Solid Fluorescence of a Pyrazoline Derivative through Hydrogen Bonding

Contact Info

Product

Resources

About