Synthesis, spectral properties, and application of 1,8‐naphthalimide fluorophores for modified polymers

Philipova, Tz.; Петков, Иван

doi:10.1002/app.1283

Cited by 7 publications

(2 citation statements)

References 5 publications

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“…The presence of an epoxy group in the structure of 1,8-naphthalimide fluorophores allows for the synthesis of molecules with novel qualities by covalent attachment to polyamide and epoxy oligomers. The development of new 1,8-naphthalimide fluorophore containing an active epoxy group to color polyamide textiles was explored in [68]. Using a standard calibration curve, colorimetric analysis revealed that 85-98% of the initial amount of fluorophore was efficiently integrated into the polyamide 6.…”

Section: Fluorescent Polymers In Fluorescent Fabricsmentioning

confidence: 99%

Fluorescence in Smart Textiles

Patti

Acierno²

2023

Encyclopedia

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Fluorescence has been identified as an advantageous feature in smart fabrics, notably for the protection of humans during outdoor athletic activities, as well as for preventing counterfeiting and determining authenticity. Fluorescence in smart fabrics is achieved using dendrimers, rare earth metal compounds, and fluorescent dye. The principal method for producing fluorescent fabrics is to immerse the sample in a solution containing fluorescent agents. However, covalent connections between fluorophores and textile substates should be established to improve the stability and intensity of the fluorescent characteristics. Fabric can be fluorescent throughout, or fluorescent fibers can be woven directly into the textile structures, made of natural (cotton, silk) or synthetic (polyamide- and polyester-based) fibers, into a precise pathway that becomes visible under ultraviolet irradiation.

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Section: Fluorescent Polymers In Fluorescent Fabricsmentioning

confidence: 99%

Fluorescence in Smart Textiles

Patti

Acierno²

2023

Encyclopedia

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“…Figure 1.12 A boronic acid-containing coumarin aldehyde sensor for glucosamine.During our work on development of new fluorescent chemosensors, we also became interested in the photophysical properties of 1,8-naphthalimides due to its highly fluorescent behavior along with excellent thermal and photochemical stabilities. They have been used as optical brighteners[67,68] and optoelectronic materials[69]. We previously studied the effect of substituent on fluorescence quantum efficiencies for this class of compounds[70] and demonstrated the application of 1,8-naphthalimides as signal transducer in a selective fluorescent sensor for Au(III) ion[71], while others have functionalized this material to become sensors for Cu(II)[72], Hg(II)[73], Cd(II)[74], Zn(II)[75], and trivalent cations[76].…”

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confidence: 99%

Novel fluorescent sensors based on 8-aminoquinoline receptor

Vongnam

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Two series of amidoquinoline-based fluorescent sensors are designed and synthesized for the selective detection of glucosamine and zinc ion in aqueous media. For the glucosamine sensors, three amidoquinoline-naphthalimide dyads are designed and synthesized in 67–73% overall yields in 3 steps from commercially available starting materials. Compounds with unsubstituted and nitro-naphthalimide show excellent selective ﬂuorescent responses towards glucosamine with the enhancement of ﬂuorescence quantum yields by 14 folds. The determination of HOMO-LUMO levels by linear sweep voltammetry suggests that the sensing mechanism likely involves the inhibition of photo-induced electron transfer (PET) between the aminoquinoline and naphthalimide moieties by glucosamine. The association constants of 1.55x104 and 1.45x104 M-1, along with the glucosamine detection limits of 1.06 and 0.29 µM are determined for unsubstituted and nitro-naphthalimide, respectively. The application of the nitro-naphthalimide derivative as a ﬂuorescent probe for real-time detection of cellular glucosamine at micromolar level in living Caco-2 cells is also demonstrated. For the zinc ion sensors, four derivatives of 8-amidoquinolines have been successfully synthesized by extension of the p-conjugated system on the quinoline ring and incorporation of either the salicylaldimine or its reduced amino form. All four compounds show selective fluorescence enhancement by zinc (II) ion, attributing to chelation-enhanced fluorescence (CHEF) effects, in which the deprotonation of the amido –NH and phenolic -OH causes the internal charge transfer (ICT) process and results in the bathochromic shift of the emission spectra. The fluorescent signals of the four compound are observed at different wavelengths in the range of 320 to 390 nm depending on the p-conjugated systems. The sensing mechanism is verified by 1H-NMR titration, Mass Spectrometry, and the X-ray crystal structure of the sensor with salicylaldimine and unsubstituted aminoquinoline, which suggests a 1:1 binding stoichiometry between this fluorophore and zinc ion. The detection limits of 0.024 to 0.431 µM and the association constants ranging from 7.0x 103 to 1.2x 104 M-1 are estimated for the four sensors.

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Preparation and fluorescent properties of poly(vinyl alcohol) bearing coumarin

Wang

Guan

et al. 2007

Polymers for Advanced Techs

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A novel water-soluble fluorescent material was prepared via ring-opening reaction between 4-methyl-7-(2,3-expoxypropoxy) coumarin (MEC) and poly(vinyl alcohol) (PVA). The fluorescent behaviors of this material (PVA-MEC) in solution, solid and film were studied in detail. The results showed that the fluorescence of PVA-MEC arose from isolated dye molecules and had a good film forming ability. In addition, the effects of acid/base environments on PVA-MEC were studied and the results showed that it was less affected by environment than 7-HMC. Moreover, relative fluorescence intensity of PVA-MEC had an excellent linear response in the temperature range of 0-60-C. These observations suggest that PVA-MEC is an excellent fluorescent macromolecular material with a convenient method of preparation and had a good water-soluble ability.

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Synthesis, spectral properties, and application of 1,8‐naphthalimide fluorophores for modified polymers

Cited by 7 publications

References 5 publications

Fluorescence in Smart Textiles

Fluorescence in Smart Textiles

Novel fluorescent sensors based on 8-aminoquinoline receptor

Preparation and fluorescent properties of poly(vinyl alcohol) bearing coumarin

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