Solid fluorescence sensors obtained by functionalization of photocrosslinked water-swollen acrylic membranes with 4-piperazine naphthalimide derivatives

Fernández-Alonso, S.; Corrales, Teresa; Pablos, Jesús L.; Catalina, Fernando

doi:10.1016/j.polymer.2017.07.039

Cited by 9 publications

(9 citation statements)

References 30 publications

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“…[15][16][17][18] Several 1,8-naphthalimide chemosensors have been developed for detection of cations, anions, and small polar molecules. [19][20][21][22] However, 1,8-naphthalimide based chemosensors with selective response to Ba 2+ remain underdeveloped. 9,23 Selective barium sensing has been demonstrated by a relatively small number of instructive fluorescent chemosensors.…”

Section: Introductionmentioning

confidence: 99%

Demonstration of Selective Single-Barium Ion Detection with Dry Diazacrown Ether Naphthalimide Turn-on Chemosensors

et al. 2021

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Single molecule fluorescence detection of barium is investigated for enhancing the sensitivity and robustness of a neutrinoless double beta decay (0νββ) search in 136 Xe, the discovery of which would alter our understanding of the nature of neutrinos and the early history of the Universe. A key developmental step is the synthesis of bariumselective chemosensors capable of incorporation into ongoing experiments in high-pressure 136 Xe gas. Here we report turn-on fluorescent naphthalimide chemosensors containing monoaza-and diaza-crown ethers as agents for single Ba 2+ detection. Monoaza-18-crown-6 ether naphthalimide sensors showed sensitivity primarily to Ba 2+ and Hg 2+ , whereas two diaza-18-crown-6 ether naphthalimides revealed a desirable selectivity toward Ba 2+ . Solution-phase fluorescence and NMR experiments support a photoinduced electron transfer mechanism enabling turn-on fluorescence sensing in the presence of barium ions. Changes in ion-receptor interactions enable effective selectivity between competitive barium, mercury, and potassium ions, with detailed calculations correctly predicting fluorescence responses. With these molecules, dry-phase single Ba 2+ ion imaging with turnon fluorescence is realized using oil-free microscopy techniques. This represents a significant advance toward a practical method of single Ba 2+ detection within large volumes of 136 Xe, plausibly enabling a background-free technique to search for the hypothetical process of 0νββ.

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Section: Introductionmentioning

confidence: 99%

Demonstration of Selective Single-Barium Ion Detection with Dry Diazacrown Ether Naphthalimide Turn-on Chemosensors

et al. 2021

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“…The time response of M3a (3 min) is higher than those of M3b (2 min), where the sensing group is linked through longer alkyl chain to the polymer matrix that impair the mobility, and the interaction of the amine group with a proton should be much easier. In general, the obtained values are lower or in the order of pH sensor immobilized in polymer matrix described in the literature [18,32,33]. Evidence for the interaction of the naphthalimide with acidic media was obtained via 1 H NMR spectroscopy of a D2O/DMSOD6 (1:2) and hydrochloric acid (DCL 37%) solution of derivatives 3a and 3b, Figure 6.…”

Section: Spectroscopic Characteristic Of Monomers (3a and 3b) And Mem...mentioning

confidence: 71%

Section: Spectroscopic Characteristic Of Monomers (3a and 3b) And Mem...mentioning

confidence: 82%

“…Those materials have found numerous applications for molecular detection in a variety of different areas, including sensor for cations, pH [8] and metal ions [9][10][11]; sensor for anions [12]; cell imaging [13,14]; detection of small molecules [15,16]; and recently have been tested as active components in antibacterial photodynamic therapy [17]. In previous work, photocrosslinked water-swollen acrylic membranes have been functionalized with piperazine naphthalimide derivatives for Hg 2+ and pH detection [18,19]. Recently, special attention has been focused on the synthesis of polymerizable naphthalimide derivatives, which can be copolymerized with different co-monomers [20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

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Solid Fluorescence pH Sensors Based on 1,8-Naphthalimide Copolymers Synthesized by UV Curing

et al. 2022

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Novel water-swollen photo-crosslinked membranes were obtained by copolymerization of the N-vinylpyrrolidone, butyl acrylate and ethyl methacrylate monomers functionalized with naphthalimide groups, as pH sensitive fluorescence probes. For that purpose, two monomers with pending naphthalimide groups anchored to ethyl methacrylate through alkyl chains with different length, were previously synthesized. The membranes were characterized using different techniques. The pH dependence of absorbance and the corresponding quenching of fluorescence were investigated and related to the structure of naphthalimide substituents linked to the membrane. The new solid sensors exhibited sensitive fluorescence changes at pH < 3, and lower time response was determined for membranes where the sensing group was linked through longer alkyl chain to the polymer matrix. The membranes were solid, thermally stable and easily handled to be applied as sensor materials, and showed a reversible behavior, which is an important feature for further fabrication of an economical on-site tool for the acidity detection in aqueous environments.

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“…Catalina and co‐workers synthesized polymer membranes, to which they attached piperazine naphthalimides through different positions ( Figure ) and studied the resulting polymers for the pH sensing ability. [ 59 ] The polymer membrane was prepared by photocrosslinking of vinyl‐pyrrolidone/butyl acrylate and ethylene glycol dimethylacrylate, together with a reactive monomer—methacryloyl chloride, which was later reacted with naphthalimide dye. This combination of hydrophobic and hydrophilic groups provides a versatility of the future applications of the membranes.…”

Section: Sensors For Cationsmentioning

confidence: 99%

Naphthalimide‐Based Fluorescent Polymers for Molecular Detection

Oshchepkov

Oshchepkova

et al. 2021

Advanced Optical Materials

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The beginning of the 21st century was marked by the intensive development of fiber‐optic sensors. New functional materials with excellent sensory properties are required to design such sensors. Fluorescent probes for neutral and charged molecules are constantly developing. However, only a small part of the reported probes was successfully converted into functional sensing polymers and found real‐world applications. A great challenge is to retain the sensing properties of a probe in a polymer matrix. The purpose of this review is to understand how properties of a probe are changed upon incorporation into a polymer and to reveal successful approaches. The review focuses on the use of the naphthalimide‐based probes in the construction of sensing polymers. The literature overview is presented according to the nature of the guest molecules targeted for the quantitative detection: cations, anions, and small organic molecules.

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Solid fluorescence sensors obtained by functionalization of photocrosslinked water-swollen acrylic membranes with 4-piperazine naphthalimide derivatives

Cited by 9 publications

References 30 publications

Demonstration of Selective Single-Barium Ion Detection with Dry Diazacrown Ether Naphthalimide Turn-on Chemosensors

Demonstration of Selective Single-Barium Ion Detection with Dry Diazacrown Ether Naphthalimide Turn-on Chemosensors

Solid Fluorescence pH Sensors Based on 1,8-Naphthalimide Copolymers Synthesized by UV Curing

Naphthalimide‐Based Fluorescent Polymers for Molecular Detection

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