Fluorescence Responses of the Protonation and Deprotonation Processes between Phenolate and Phenol within Rosamine

Yang, Ling; Niu, Jin-Yun; Zhan, Yan-Hua; Xu, Yu-Jie; Sun, Rong; Ge, Jian‐Feng

doi:10.1002/cjoc.201700534

Cited by 8 publications

(2 citation statements)

References 45 publications

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“…The purpose being to assess the possible influence of the protonation state of enol moiety found in the coumarin fragment. For all compounds, only a very weak yellow‐orange fluorescence emission intensity was observed, whatever the substitution pattern of coumarin and pyronin units [3ai] . It prevented us to accurately determine relative fluorescence quantum yields, roughly estimated at less than 1 %.…”

Section: Resultsmentioning

confidence: 94%

Coumarin‐Pyronin Hybrid Dyes: Synthesis, Fluorescence Properties and Theoretical Calculations**

Renault¹,

Chevalier

Bignon

et al. 2021

ChemPhotoChem

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A novel class of rosamine dyes bearing a 7-substituted 4-hydroxycoumarin unit as meso-heteroaryl ring is presented. The latent C-nucleophilic character of 4-hydroxycoumarin derivatives (i.e., their C-3 position as nucleophilic center) has been drawn on in the designing of two unprecedented synthetic routes towards these atypical xanthene dyes. They are based on an effective formal Knoevenagel condensation with either pyronin derivatives or a mixed bis-aryl ether bearing both an aldehyde and a masked phenylogous amine, possibly applicable to a wide range of latent cyclic C-nucleophiles. We also report experimental and theoretical photophysical investigations of these unique coumarin-pyronin hybrid structures and particularly their form low-lying quenching states, some of dark twisted intramolecular charge transfer (TICT) nature, depending on the medium (CHCl 3 and water). Furthermore, two fluorophore compounds 9 and 11 have been applied for imaging in paraformaldehyde-fixed A549 cells to gain insights into their permeation and localization. File list (2)download file view on ChemRxiv Publication-KR02-Preprint-VF.pdf (4.47 MiB) download file view on ChemRxiv Publication-KR02-Preprint-SI-VF.pdf (11.37 MiB)

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Section: Resultsmentioning

confidence: 94%

Coumarin‐Pyronin Hybrid Dyes: Synthesis, Fluorescence Properties and Theoretical Calculations**

Renault¹,

Chevalier

Bignon

et al. 2021

ChemPhotoChem

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“…Pyronin derivatives are chemically stable fluorophores that possess high molar absorption coefficients and high fluorescence quantum yields. ,− Many pH sensors exhibiting a high sensitivity in near-alkaline pH suffer from some drawbacks, such as low fluorescence quantum yields, high lipophilicity, or emit only in the blue region of visible light (see the Supporting Information for details, Table S10). Here, we designed and synthesized a library of novel fluorescent 9-iminopyronin derivatives possessing unique and distinct emission properties with the aim of providing optimal sensitivity at neutral to near-alkaline conditions (Supporting Information).…”

Section: Results and Discussionmentioning

confidence: 99%

Fluorescent pH Indicators for Neutral to Near-Alkaline Conditions Based on 9-Iminopyronin Derivatives

et al. 2019

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Monitoring enzymatic activities at pH ranges compatible with their physiological optimum using fluorescent assays is important for high-throughput screening and engineering of novel biocatalysts as well as applications in biosensing and diagnostics. However, the number of fluorescent dyes exhibiting necessary optical properties at alkaline pHs is limited. Here, we report the design, synthesis, and biochemical application of fluorescent 9-iminopyronin derivatives possessing unique and distinct emission properties to provide optimal sensitivity at neutral to near-alkaline conditions. They exist in two acid−base forms, allowing for a dual-emission ratiometric sensing with a linear response of pH between 6.0 and 8.5 and detection sensitivity of a 0.06 pH unit. Selected fluorophores were used as the sensors for monitoring the enzymatic hydrolytic activity of a model enzyme haloalkane dehalogenase.

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Multiple Hydrogen Bonds Promoted ESIPT and AIE‐active Chiral Salicylaldehyde Hydrazide

et al. 2018

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The simpler, the better! A series of simple and highly fluorescent salicylaldehyde hydrazide molecules (41 samples) have been designed and prepared. Even though these soft materials contain a very small π‐conjugated system, they can go through multiple intramolecular and intermolecular hydrogen bonds promoted excited‐state intramolecular proton‐transfer (ESIPT) to display strong blue, green, yellow, and orange aggregation‐induced emission (AIE) with large Stokes shifts (up to 184 nm) and high fluorescence quantum yields (Ф up to 0.20). Unusual mechanochromic fluorescence enhancements are also found in some solid samples. Through coordination, hydrogen and halogen bonds, these flexible molecules can be used as Mg2+ (Ф up to 0.46) probes, universal anion (Ф up to 0.14) and unprotected amino acids (Ф up to 0.16) probes, and chiral diamine (enantiomeric selectivity and Ф up to 0.36 and 0.062, respectively) receptors. Combining their advantages of AIE and biocompatibility, these low cytotoxic dyes have potential application in living cell imaging. Furthermore, the effects of different functional groups on the molecule arrangement, ESIPT, AIE, probe, and chiral recognition properties are also examined, which provide a simple and bright paradigm for the design of multiple‐stimuli‐responsive smart materials.

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Fluorescence Responses of the Protonation and Deprotonation Processes between Phenolate and Phenol within Rosamine

Cited by 8 publications

References 45 publications

Coumarin‐Pyronin Hybrid Dyes: Synthesis, Fluorescence Properties and Theoretical Calculations**

Coumarin‐Pyronin Hybrid Dyes: Synthesis, Fluorescence Properties and Theoretical Calculations**

Fluorescent pH Indicators for Neutral to Near-Alkaline Conditions Based on 9-Iminopyronin Derivatives

Multiple Hydrogen Bonds Promoted ESIPT and AIE‐active Chiral Salicylaldehyde Hydrazide

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