Structural Characterization of Mono and Dihydroxylated Umbelliferone Derivatives

Seoane-Rivero, Rubén; Ruiz-Bilbao, Estibaliz; Navarro, Rodrigo; Laza, José Manuel; Cuevas, José María; Artetxe, Beñat; Gutiérrez‐Zorrilla, Juan M.; Vilas-Vilela, José Luis; Marcos‐Fernández, Ángel

doi:10.3390/molecules25153497

Cited by 12 publications

(10 citation statements)

References 45 publications

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“…While the open variant has a significant absorption at wavelengths longer than 300 nm, due to the strong π–π*-transition of the pyrone structure, this absorbance band is missing for dimeric coumarin structures. The value of the absorbance maximum above 300 nm is directly connected to the degree of cyclization and can be used for detection . In Figure , absorption spectra of the open and closed configuration thin films with the marked absorption band at wavelength 321 nm are shown.…”

Section: Resultsmentioning

confidence: 99%

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Intramolecular Coumarin-Dimer Containing Polyurethanes: Optical Tuning via Single- and Two-Photon Absorption Processes

et al. 2022

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The synthesis of an isomer-pure intramolecular coumarin dimer (ICD) in virtually unlimited amounts using a photo flow reactor is described. Based on this compound, polyurethanes with different ratios of hexamethylene diisocyanate and polytetrahydrofuran were synthesized and characterized. The reversibility of the photoinduced cycloaddition and cycloreversion reactions, one of the critical features, was compared for polymers prepared from closed ICDs and open ICDs. It was found that closed ICDs lead to a pre-orientation of the photoactive groups in the polymers, which results in a reduced loss in photoswitchable absorption. By varying the ICD content of the polymers, refractive indices ranging from 1.47 to 1.59 were achieved. With illumination, refractive index changes of Δn ≥ 0.02, as well as fluorescence changes, were achieved. Photoreactions induced by both single-photon absorption (SPA) and two-photon absorption (TPA) were studied. For the TPA-induced reaction, an autocatalytically sensitized mechanism was found. These novel polymers based on an intramolecular dimeric coumarin compound have great potential as optical materials with light-switchable properties, in particular, by TPA processes.

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Section: Resultsmentioning

confidence: 99%

“…The value of the absorbance maximum above 300 nm is directly connected to the degree of cyclization and can be used for detection. 36 In Figure 4 another dimer. Associated with these three main questions are the occurrence of the isomeric distributions and cross-linking reactions.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Intramolecular Coumarin-Dimer Containing Polyurethanes: Optical Tuning via Single- and Two-Photon Absorption Processes

et al. 2022

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“…The band at 273 nm of CM and the shoulder at 294 nm of 7OHCM are attributed to the π → π* transitions of the conjugated electrons of the benzene ring, while the bands at 312 and 320 nm are attributed to the π → π* transitions of the pyrone nucleus. 43 In the presence of copper, it is observed that both bands increase in intensity, indicating the perturbation of the ligand's orbitals in the presence of the metal.…”

Section: Coppermentioning

confidence: 99%

Electrochemistry Applied to the Evaluation of the Interaction between Coumarins and the Copper Metal Ion: An Experimental Study with a DFT-Based Analysis

Ferreira¹,

Bettanin²,

Honório³

et al. 2022

J. Electrochem. Soc.

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Coumarin belongs to the benzopyrones family commonly found in vegetables such as Guaco. These compounds have a diversity of applications, especially in medicine, because they have vasodilatory, anti-inflammatory, anti-asthmatic, and anti-allergic properties. In addition, metal complexes using coumarins in their structures have been widely studied for therapeutic purposes. Due to the importance of these molecules, in this work, was studied the interaction between coumarin (CM) and 7-hydroxycoumarin (7OHCM), the main metabolite of coumarin, with the metal ion copper (II), which is naturally present in the environment. Cyclic voltammetry studies showed a reduction peak at 0.39 V and an oxidation peak at 0.47 V for the Cu-CM complex under pencil graphite electrode. Cu-7OHCM showed a reduction peak at 0.40 V and an oxidation peak at 0.49 V, both with reversible process characteristics. In the presence of coumarin, Cu+ is stabilized in solution. Theoretical data suggest the formation of the complex and stabilization of Cu+ in solution. After the interaction, a decrease in the energy of the system occurs, as well as an overlap of the HOMO orbitals of the two species was observed. Furthermore, the studies indicated that the Cu-CM complex is more stable than the Cu-7OHCM complex.

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“…The band above 300 nm, centered at about 318 nm, absent in the spectrum of poly(EDMA) (Figure S4), is characteristic of the 2-pyrone structure of coumarins, while the band below 300 nm, centered at about 280 nm, is characteristic of π−π* transitions of the aromatic structures present in both the CouMA and EDMA moieties. 44,45 The decrease of the intensity of the signal at 318 nm during irradiation with UVA reflects the opening of the 3,4 double bond in the 2-pyrone structure to form the cyclobutane ring when coumarin dimers are formed. 45,46 The photocycloaddition of the coumarin pendant moieties proceeded during irradiation with UVA.…”

Section: ■ Introductionmentioning

confidence: 99%

Biobased Composites from Eugenol- and Coumarin-Derived Methacrylic Latex and Hemp Nanocellulose: Cross-Linking via [2 + 2] Photocycloaddition and Barrier Properties

Dalle Vacche,

Molina-Gutiérrez,

Ferraro

et al. 2024

ACS Sustainable Chem. Eng.

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A novel-biobased latex was synthesized by redoxinitiated emulsion copolymerization of ethoxy dihydroeugenyl methacrylate with 5 wt % of a photosensitive methacrylate containing a coumarin group. A stable copolymer latex having 16 wt % solids content and a particle size of 53 nm was obtained. The copolymer had a T g of 29 °C and was soluble in acetone. Coatings were obtained, and the effect of UVA irradiation was tested: the light-induced cross-linking of the copolymer by [2 + 2] cycloaddition of the coumarin pendant moieties was demonstrated by UV−visible spectroscopy. As a consequence of UVA-induced cross-linking, the copolymer became insoluble in acetone. The copolymer latex was combined with hemp-derived nanocellulose to obtain composite self-standing films by simple mixing in an aqueous medium followed by casting, evaporation of water, and hot pressing. The composite films were also successfully cross-linked by [2 + 2] cycloaddition, with an enhancement of barrier properties. The water vapor transmission rate of the cross-linked composite films with up to 45 wt % nanocellulose was 5 times lower than that of the hemp nanocellulose film, while further addition of nanocellulose increased permeability.

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Structural Characterization of Mono and Dihydroxylated Umbelliferone Derivatives

Cited by 12 publications

References 45 publications

Intramolecular Coumarin-Dimer Containing Polyurethanes: Optical Tuning via Single- and Two-Photon Absorption Processes

Intramolecular Coumarin-Dimer Containing Polyurethanes: Optical Tuning via Single- and Two-Photon Absorption Processes

Electrochemistry Applied to the Evaluation of the Interaction between Coumarins and the Copper Metal Ion: An Experimental Study with a DFT-Based Analysis

Biobased Composites from Eugenol- and Coumarin-Derived Methacrylic Latex and Hemp Nanocellulose: Cross-Linking via [2 + 2] Photocycloaddition and Barrier Properties

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