A multi-state fluorescence switch based on a new photochromic diarylethene with a di-(ethyl-1,8-naphthalimidyl)amine unit

Wei, Shasha; Zheng, Chunhong; Liu, Gang; Chen, Bing; Pu, Shouzhi

doi:10.1016/j.jphotochem.2015.04.007

Cited by 11 publications

(7 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…20 Pu et al reported the synthesis of di(ethyl-1,8-naphthalimidyl)amine for the selective detection of Sn 2+ ion. 21 Later, Adhikari et al described the synthesis and bioimaging application of 4-(naphthalen-1ylethynyl) aniline appended rhodamine for Sn 2+ ion. 7 Sekar et al reported the benzophenone fluorescence chemosensor for Sn 2+ ion.…”

Section: ■ Introductionmentioning

confidence: 99%

Naphthoquinone-Dopamine Linked Colorimetric and Fluorescence Chemosensor for Selective Detection of Sn²⁺ Ion in Aqueous Medium and Its Bio-Imaging Applications

Ravichandiran

Prabakaran

Bella³

et al. 2020

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

A simple naphthoquinone−dopamine hybrid (2CND) was designed and fabricated as a colorimetric and fluorescence chemosensor for the selective recognition of Sn 2+ in the aqueous medium. This simply accessible chemosensor was prepared by connecting of naphthoquinone acceptor and dopamine donor moieties via Michael-like addition reaction. The chemosensor 2CND showed a turn-on fluorescence response which operated through the inhibited photoinduced electron transfer effect. The sensor probe shows remarkable performance, such as high selectivity, sensitivity, excellent water solubility, and rapid response to Sn 2+ (less than 5 s). The detection mechanism of the 2CND−Sn 2+ complex was supported by FT-IR analysis, 1 H NMR titration, and DFT calculations. Besides, the 1:1 binding stoichiometry was confirmed by the ESI-MS spectral analysis. Furthermore, the chemosensor 2CND has been successfully employed as a fluorescence probe to monitor trace Sn 2+ in live cells and zebrafish. The sensor probe 2CND could serve as an effective fluorescence bioimaging probe for the discriminative detection of diseased and normal human cells.

show abstract

Section: ■ Introductionmentioning

confidence: 99%

Naphthoquinone-Dopamine Linked Colorimetric and Fluorescence Chemosensor for Selective Detection of Sn²⁺ Ion in Aqueous Medium and Its Bio-Imaging Applications

Ravichandiran

Prabakaran

Bella³

et al. 2020

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

show abstract

“…Generally, Sn(II) can pollute the water system which induces the toxicity to algae, phytoplankton, and fungi. 13 Phytoplankton is an important microorganism which delivers oxygen to the other microorganisms in water. This is a significant measure of the food chain in the aquatic system.…”

mentioning

confidence: 99%

“…Then, 13 C NMR analysis was investigated to confirm the reduction reaction-enabled sensing mechanism of the probe 4CBS. Strong signals for −CO groups in the naphthoquinone moiety were obtained at 176.9433 and 179.9464 ppm.…”

mentioning

confidence: 99%

“…Specifically, the carbon signals for −C−OH groups in the reduced form of 4CBS were found at 141.7613 and 143.5276 ppm (Figure 8). After 13 C NMR titration analysis, distortionless enhancement by polarization transfer (DEPT) NMR analysis was carried out to determine if any of the aromatic rings that participated in the reduction reaction was induced by Sn 2+ . Eight tertiary carbons are present in the chemosensing probe 4CBS.…”

mentioning

confidence: 99%

“…In the environmental perspective, Sn(II) can remain in the environment for a longer time and fairly remain non-biodegradable, while the accumulation of Sn(II) for several years on water soils distresses the microorganisms. Generally, Sn(II) can pollute the water system which induces the toxicity to algae, phytoplankton, and fungi . Phytoplankton is an important microorganism which delivers oxygen to the other microorganisms in water.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Simple Colorimetric and Fluorescence Chemosensing Probe for Selective Detection of Sn²⁺ Ions in an Aqueous Solution: Evaluation of the Novel Sensing Mechanism and Its Bioimaging Applications

Ravichandiran

Kaliannagounder

Bella³

et al. 2020

Anal. Chem.

View full text Add to dashboard Cite

An easily accessible colorimetric and fluorescence probe 4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)benzenesulfonamide (4CBS) was successfully developed for the selective and sensitive detection of Sn 2+ in an aqueous solution. The sensing mechanism involves reduction of −CO into −C− OH groups in 4CBS upon the addition of Sn 2+ , which initiates the fluorescence turn-on mode. A better linear relationship was achieved between fluorescence intensity and Sn 2+ concentration in the range of 0−62.5 μM, with a detection limit (LOD) of 0.115 μM. The binding mechanism of 4CBS for Sn 2+ was confirmed by Fourier transform infrared analysis, NMR titrations, and mass (electrospray ionization) spectral analysis. Likewise, the proposed sensing mechanism was supported by quantum chemical calculations. Moreover, bioimaging studies demonstrated that the chemosensing probe 4CBS is an effective fluorescent marker for the detection of Sn 2+ in living cells and zebrafish. Significantly, 4CBS was able to discriminate between Sn 2+ in human cancer cells and Sn 2+ in normal live cells.

show abstract

Multi-controllable properties of an antipyrine-based diarylethene and its high selectivity for recognition of Al 3+

Zhang

Fan

et al. 2016

Dyes and Pigments

View full text Add to dashboard Cite

A multi-state fluorescence switch based on a new photochromic diarylethene with a di-(ethyl-1,8-naphthalimidyl)amine unit

Cited by 11 publications

References 36 publications

Naphthoquinone-Dopamine Linked Colorimetric and Fluorescence Chemosensor for Selective Detection of Sn²⁺ Ion in Aqueous Medium and Its Bio-Imaging Applications

Naphthoquinone-Dopamine Linked Colorimetric and Fluorescence Chemosensor for Selective Detection of Sn²⁺ Ion in Aqueous Medium and Its Bio-Imaging Applications

Simple Colorimetric and Fluorescence Chemosensing Probe for Selective Detection of Sn²⁺ Ions in an Aqueous Solution: Evaluation of the Novel Sensing Mechanism and Its Bioimaging Applications

Multi-controllable properties of an antipyrine-based diarylethene and its high selectivity for recognition of Al 3+

Contact Info

Product

Resources

About

A multi-state fluorescence switch based on a new photochromic diarylethene with a di-(ethyl-1,8-naphthalimidyl)amine unit

Cited by 11 publications

References 36 publications

Naphthoquinone-Dopamine Linked Colorimetric and Fluorescence Chemosensor for Selective Detection of Sn2+ Ion in Aqueous Medium and Its Bio-Imaging Applications

Naphthoquinone-Dopamine Linked Colorimetric and Fluorescence Chemosensor for Selective Detection of Sn2+ Ion in Aqueous Medium and Its Bio-Imaging Applications

Simple Colorimetric and Fluorescence Chemosensing Probe for Selective Detection of Sn2+ Ions in an Aqueous Solution: Evaluation of the Novel Sensing Mechanism and Its Bioimaging Applications

Multi-controllable properties of an antipyrine-based diarylethene and its high selectivity for recognition of Al 3+

Contact Info

Product

Resources

About

Naphthoquinone-Dopamine Linked Colorimetric and Fluorescence Chemosensor for Selective Detection of Sn²⁺ Ion in Aqueous Medium and Its Bio-Imaging Applications

Naphthoquinone-Dopamine Linked Colorimetric and Fluorescence Chemosensor for Selective Detection of Sn²⁺ Ion in Aqueous Medium and Its Bio-Imaging Applications

Simple Colorimetric and Fluorescence Chemosensing Probe for Selective Detection of Sn²⁺ Ions in an Aqueous Solution: Evaluation of the Novel Sensing Mechanism and Its Bioimaging Applications