Design and characterization of pH-sensitive spirorhodamine 6G probes with aliphatic substituents

Paolo, Matias Andres Di; Boubeta, Fernando Martín; Alday, Julieta Ruth; Torino, Mateo Michel; Aramendı́a, Pedro F.; Suárez, Sebastián; Bossi, Mariano L.

doi:10.1016/j.jphotochem.2019.112011

Cited by 5 publications

(5 citation statements)

References 38 publications

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“…One of the most studied modifications is the conversion of the carboxylic acid of rhodamine B into an amide, which can adopt two forms: a closed, spirolactam form in which the fluorescence of the xanthene core is quenched due to the disruption of conjugation, or an open form, which is fluorescent (Figure a). The transition from the closed to open form is sensitive to both pH − and ultraviolet illumination, − which enables the use of rhodamine spirolactams (RSLs) in sensing or other dye-activation on/off switching applications.…”

Section: Introductionmentioning

confidence: 99%

“…The pH-sensitive transition of RSLs between the closed, deprotonated form and the open, protonated form is dependent on substituent groups attached to the nitrogen of the amide. − Studies indicate that the kinetics and pKa values of RSLs are governed by both the sterics ,, and electron-withdrawing/donating nature ,,, of the amide substituents. In general, increasing the size and electron-withdrawing character of the substituent groups shifts pKa values to higher numbers .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Optical Characterization of a Rhodamine B Spirolactam Dimer

et al. 2022

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Amide derivatives of xanthene dyes such as rhodamine B are useful in a variety of sensing applications due to their colorimetric responses to stimuli such as acidity changes and UV light. The optical properties of these molecules can be influenced by intermolecular associations into dimeric structures, but the exact impact can be hard to predict. We have designed a covalently linked intramolecular dimer of the dye rhodamine B utilizing p-phenylenediamine to link the two dyes via amide bonds. The doubly closed spirolactam version of this dimer, RSL 2 , is isolated as a colorless solid. Under acidic conditions or UV exposure, RSL 2 solutions develop a pink color that is expected for the ring-opened form of the molecule. However, nuclear magnetic resonance (NMR) and single-crystal diffraction data show that the equilibrium still prefers the closed dimer state. Interestingly, the emission profile of RSL 2 shows solvatochromic blue fluorescence. Control studies of model compounds with similar structural motifs do not display similar blue fluorescence, indicating that this optical behavior is unique to the dimeric form. This behavior may lend itself to applications of such xanthene dimers to more sophisticated sensors beyond those with traditional binary on/off fluorescence profiles.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Optical Characterization of a Rhodamine B Spirolactam Dimer

et al. 2022

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show abstract

Section: Introductionmentioning

confidence: 99%

“…Studies indicate that the kinetics and pKa values of RSLs are governed by both the sterics 8,[12][13] and electron withdrawing/donating nature 7,[9][10]12 of the amide substituents. In general, increasing the size and electron-withdrawing character of the substituent groups shifts pKa values to higher numbers 12 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Optical Characterization of a Rhodamine B Spirolactam Dimer

Stratton

Pierre

Riser

et al. 2022

Preprint

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Amide derivatives of xanthene dyes such as rhodamine B are useful in a variety of sensing applications due to their colorimetric responses to stimuli such as acidity changes and UV light. The optical properties of these molecules can be influenced by intermolecular associations into dimeric structures, but the exact impact can be hard to predict. We have designed a covalently linked intramolecular dimer of the dye rhodamine B utilizing p-phenylene diamine to link the two dyes via amide bonds. The doubly closed spirolactam version of this dimer, RSL2, is isolated as a colorless solid. Under acidic conditions or UV exposure, RSL2 solutions develop a pink color that is expected for the ring-opened form of the molecule. However, NMR and single crystal diffraction data show that the equilibrium still prefers the closed dimer state. Interestingly, the emission profile of RSL2 shows solvatochromic blue fluorescence. Control studies of model compounds with similar structural motifs do not display similar blue fluorescence, indicating that this optical behavior is unique to the dimeric form. This behavior may lend itself to applications of such xanthene dimers to more sophisticated sensors beyond those with traditional binary on/off fluorescence profiles.

show abstract

“…The transition from the closed to open form is sensitive to both pH and ultraviolet illumination, which enables the use of rhodamine spirolactams (RSLs) in sensing or other dye-activation on/off switching applications. The pH-sensitive transition of RSLs between the closed, deprotonated form and the open, protonated form is dependent on substituent groups attached to the nitrogen of the amide [6][7][8][9][10][11][12][13] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Optical Characterization of a Rhodamine B Spirolactam Dimer

Stratton

Pierre

Riser

et al. 2022

Preprint

View full text Add to dashboard Cite

Amide derivatives of xanthene dyes such as rhodamine B are useful in a variety of sensing applications due to their colorimetric responses to stimuli such as acidity changes and UV light. The optical properties of these molecules can be influenced by intermolecular associations into dimeric structures, but the exact impact can be hard to predict. We have designed a covalently linked intramolecular dimer of the dye rhodamine B utilizing p-phenylene diamine to link the two dyes via amide bonds. The doubly closed spirolactam version of this dimer, RSL2, is isolated as a colorless solid. Under acidic conditions or UV exposure, RSL2 solutions develop a pink color that is expected for the ring-opened form of the molecule. However, NMR and single crystal diffraction data show that the equilibrium still prefers the closed dimer state. Interestingly, the emission profile of RSL2 shows solvatochromic blue fluorescence. Control studies of model compounds with similar structural motifs do not display similar blue fluorescence, indicating that this optical behavior is unique to the dimeric form. This behavior may lend itself to applications of such xanthene dimers to more sophisticated sensors beyond those with traditional binary on/off fluorescence profiles.

show abstract

Design and characterization of pH-sensitive spirorhodamine 6G probes with aliphatic substituents

Cited by 5 publications

References 38 publications

Synthesis and Optical Characterization of a Rhodamine B Spirolactam Dimer

Synthesis and Optical Characterization of a Rhodamine B Spirolactam Dimer

Synthesis and Optical Characterization of a Rhodamine B Spirolactam Dimer

Synthesis and Optical Characterization of a Rhodamine B Spirolactam Dimer

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