Surface modification of poly(ethylene-butyl acrylate) copolymers by microwave methodology and functionalization with 4-dimethylamino- N -(2-hydroxyethyl)-1,8-naphthalimide for acidity sensing

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

doi:10.1016/j.reactfunctpolym.2016.08.009

Cited by 12 publications

(6 citation statements)

References 38 publications

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“…Spectra exhibited absorption maxima around 445 nm, Table 2. That band has been attributed to intramolecular electron charge transfer (ICT), which is associated with electron donor-acceptor interaction which takes place between the unbound electron pair of the nitrogen atom at C-4 position and the electron-accepting pericarboiximide groups [24]. The fluorescence spectra showed emission maxima at 546 nm, and the fluorescence quantum yield was low in polar media but was drastically increased to 0.77 in hexane, which agrees with the results obtained by other authors [31].…”

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

confidence: 99%

“…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]. On the other hand, a new procedure for the functionalization of the surface of membranes based on a copolymer of ethylene butyl acrylate with 4-dimethylamino-N-(2-hydroxyethyl)-1,8-naphthalimide derivatives has been reported for acidity sensing [24]. In that case, the mechanism responsible for the sensory properties of naphthalimide was intramolecular charge transfer (ICT); when the aromatic amine was protonated at low pH values fluorescence, it was quenched.…”

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

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2022

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“…A poly(ethylene‐butyl acrylate) copolymer (EBA) was modified and functionalized by naphthalimide derivative yielding pH sensor P24‐E ( Figure a). [ 105 ] At low pH values the aromatic amine of the naphthalimide‐derivative was protonated and a decrease in absorbance and the corresponding quenching of fluorescence was observed. The p K a values of the free naphthalimide derivative and the polymer, measured in water:ethanol (4:1, v/v) mixture, were different: −0.88 for P24‐E and 1.41 for 24 .…”

Section: Sensors For Anionsmentioning

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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“…are used as a signal fragment in the design of PET sensor systems [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. Very important among these are the derivatives of 1,8-naphthalimide, which depending on the nature of the C-4 substituents, may emit blue or yellow-green fluorescence [ 14 , 15 , 16 , 17 ]. In most cases, this position contains receptor fragments that can react with the analytes tested, which determines the color of the fluorescence emitted by the sensor [ 4 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Photophysical Characterization, and Sensor Activity of New 1,8-Naphthalimide Derivatives

Yordanova

Cheshmedzhieva

Stoyanov

et al. 2020

Sensors

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Three new 1,8-naphthalimide derivatives M1–M3 with different substituents at the C-4 position have been synthesized and characterized. Their photophysical properties have been investigated in organic solvents of different polarity, and their fluorescence intensity was found to depend strongly on both the polarity of the solvents and the type of substituent at C-4. For compounds M1 and M2 having a tertiary amino group linked via an ethylene bridge to the chromophore system, high quantum yield was observed only in non-polar media, whereas for compound M3, the quantum efficiency did not depend on the medium polarity. The effect of different metal ions (Ag+, Ba2+, Cu2+, Co2+, Mg2+, Pb2+, Sr2+, Fe3+, and Sn2+) on the fluorescence emission of compounds M1 and M2 was investigated. A significant enhancement has been observed in the presence of Ag+, Pb2+, Sn2+, Co2+, Fe3+, as this effect is expressed more preferably in the case of M2. Both compounds have shown significant pH dependence, as the fluorescence intensity was low in alkaline medium and has been enhanced more than 20-fold in acidic medium. The metal ions and pH do not affect the fluorescence intensity of M3. Density-functional theory (DFT) and Time-dependent density-functional theory (TDDFT) quantum chemical calculations are employed in deciphering the intimate mechanism of sensor mechanism. The functional properties of M1 and M2 were compared with polyamidoamine (PAMAM) dendrimers of different generations modified with 1,8-naphthalimide.

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Surface modification of poly(ethylene-butyl acrylate) copolymers by microwave methodology and functionalization with 4-dimethylamino- N -(2-hydroxyethyl)-1,8-naphthalimide for acidity sensing

Cited by 12 publications

References 38 publications

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

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

Naphthalimide‐Based Fluorescent Polymers for Molecular Detection

Synthesis, Photophysical Characterization, and Sensor Activity of New 1,8-Naphthalimide Derivatives

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