Substituted xanthylocyanines. III. Dyes containing non-symmetrically substituted xanthylium core

Poronik, Ye.M.; Shandura, Mykola P.; Kovtun, Yu. P.

doi:10.1016/j.dyepig.2005.08.017

“…To avoid the substitution with the chlorine atom we switched to O -protected xanthylium salts. Compound 1 was alkylated with methyl 4-toluenesufonate according to the known procedure . Methoxyxanthylium salt 8 was transformed into vinamidinium derivative 9 following the strategy described for dye 1 (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…3-Diethylamino-6-hydroxy-substituted xanthylium salt 1 63 was chosen as the key substrate for the synthesis of the rhodolbased chemosensor. In the first attempt, compound 1 was treated with the Vilsmeier reagent.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Nonlinear Optical Chemosensor for Sodium Ion Based on Rhodol Chromophore

Poronik

¹

,

Clermont

²

,

Blanchard‐Desce

³

et al. 2013

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As part of a strategy to identify good fluorescent probes based on two-photon excited fluorescence (TPEF), the sensor for sodium cation has been designed bearing a rhodol chromophore linked with an aza-crown ether. An efficient synthetic route to rhodol derivatives possessing five-membered heterocycles at position 9 and their precursors that contain xanthylium salt has been developed. The synthesis involves condensation of xanthylium salts bearing vinamidinium moiety at position 9, with phenylhydrazine derivatives as the key step. To accomplish the synthesis of derivatives bearing 1-aza-15-crown-5 and 1,10-diaza-18-crown-6, the Buchwald-Hartwig reaction has been employed in the final stage. Electronic spectra of all prepared rhodols display strong absorption in the range of 450-550 nm with well-resolved vibronic bands, which maintains its fine structure in a wide range of solvents. The most intensive two-photon absorption (2PA) band in the rhodol spectrum (165 GM), located at shorter wavelengths, matches well with the short-wavelength absorption band in the linear electronic spectrum and is most probably related to the two-photon allowed electronic transition S0→S2. The influence of cation binding on one- and two-photon spectroscopic properties of rhodol linked with 1-aza-15-crown-5 via the phenylpyrazole bridge has been investigated. This probe exhibits high sensitivity and good selectivity for Na(+) in CH3CN. The mechanism involves the complexation of the Na(+) by 1-aza-15-crown-5 in the probe, which induces prominent fluorescence enhancement via quenching of electron-transfer. Interestingly, the complexation with Na(+) led to a significant increase of the 2PA band in the 750-800 nm region (corresponding to a two-photon allowed, one-photon forbidden transition) for rhodol bearing 1-aza-15-crown-5, which led to the overall enhancement of the TPEF signal (approximately an order of magnitude). Thus, a turn-on fluorescent probe for sodium ion, which does not respond to many other metal species, has been constructed.

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“…Rational hybridization of molecules to rhodamine can expand the diversity of rhodamine dyes and the application of rhodamine.Therefore, there is still ample scope for the development of new hybrid rhodamine dyes.B eside rhodamines,o ther fluorophores can also be hybridized to yield desired photophysical properties. Prominent examples include ESIPT-BODIPY, [96] ESIPTcoumarin, [97] BODIPY-coumarin, [98] naphthofluorescein, [73,99] and cyanine-FITC dyes. [74,100] Of course,t here are still some obstacles,such as low water solubility and low quantum yield of NIR fluorophores,that must be overcome.Inour group,we are utilizing the hybridization between rhodamine dyes and TP fluorophores to construct novel hybrid rhodamine dyes with good solubility,h igh quantum yield, and long emission wavelengths for use in bioimaging applications.…”

Section: Methodsmentioning

confidence: 99%

Hybrid Rhodamine Fluorophores in the Visible/NIR Region for Biological Imaging

Wang

¹

,

Du

²

,

Hu

³

et al. 2019

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Fluorophores and probes are invaluable for the visualization of the location and dynamics of gene expression, protein expression, and molecular interactions in complex living systems. Rhodamine dyes are often used as scaffolds in biological labeling and turn‐on fluorescence imaging. To date, their absorption and emission spectra have been expanded to cover the entire near‐infrared region (650–950 nm), which provides a more suitable optical window for monitoring biomolecular production, trafficking, and localization in real time. This review summarizes the development of rhodamine fluorophores since their discovery and provides strategies for modulating their absorption and emission spectra to generate specific bathochromic‐shifts. We also explain how larger Stokes shifts and dual‐emissions can be obtained from hybrid rhodamine dyes. These hybrid fluorophores can be classified into various categories based on structural features including the alkylation of amidogens, the substitution of the O atom of xanthene, and hybridization with other fluorophores.

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“…However, owing to the replacement of the C3 with indolium units, the fluorophores cannot be readily made by the interconversion between the fluorescent open form and the nonfluorescent spirocyclic form. In 2007, Kovtun's group reported some cyanine–rhodamine dyes ( 153 – 155 ) that lack the spirocyclic structure . In order to avoid the disadvantage conferred by this missing spirocyclic structure, Lin's group developed cyanine–FITC‐based dyes that can be regulated by modifications of the critical hydroxy group …”

Section: Hybrid Cyanine–rhodamine Dyesmentioning

confidence: 99%

Hybrid Rhodamine Fluorophores in the Visible/NIR Region for Biological Imaging

Wang

¹

,

Du

²

,

Hu

³

et al. 2019

View full text Add to dashboard Cite

Fluorophores and probes are invaluable for the visualization of the location and dynamics of gene expression, protein expression, and molecular interactions in complex living systems. Rhodamine dyes are often used as scaffolds in biological labeling and turn‐on fluorescence imaging. To date, their absorption and emission spectra have been expanded to cover the entire near‐infrared region (650–950 nm), which provides a more suitable optical window for monitoring biomolecular production, trafficking, and localization in real time. This review summarizes the development of rhodamine fluorophores since their discovery and provides strategies for modulating their absorption and emission spectra to generate specific bathochromic‐shifts. We also explain how larger Stokes shifts and dual‐emissions can be obtained from hybrid rhodamine dyes. These hybrid fluorophores can be classified into various categories based on structural features including the alkylation of amidogens, the substitution of the O atom of xanthene, and hybridization with other fluorophores.

show abstract

Substituted xanthylocyanines. III. Dyes containing non-symmetrically substituted xanthylium core

Cited by 17 publications

References 5 publications

Nonlinear Optical Chemosensor for Sodium Ion Based on Rhodol Chromophore

Nonlinear Optical Chemosensor for Sodium Ion Based on Rhodol Chromophore

Hybrid Rhodamine Fluorophores in the Visible/NIR Region for Biological Imaging

Hybrid Rhodamine Fluorophores in the Visible/NIR Region for Biological Imaging

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