Searching for fluorescent nanocrystals in aqueous solutions of 7-methoxycoumarin

Fery–Forgues, Suzanne; Cantuel, Martine; Fournier‐Noël, Clara

doi:10.1016/j.dyepig.2010.04.002

Cited by 12 publications

(3 citation statements)

References 32 publications

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“…During the reprecipitation process, absorbance was markedly decreased, which indicates the formation of particles. Meanwhile, the shape of the absorption spectrum hardly changed with time, as already observed during the formation of nanocrystals from other organic dyes. , No further evolution of the spectrum was detected after 10 min, which suggests that the reprecipitation process was achieved.…”

Section: Resultsmentioning

confidence: 53%

“…To obtain smaller particles, the reprecipitation method was used . This simple and soft method, based on a solvent exchange, has been widely developed during the past few years and has proved to be very useful in the group to prepare nano- and microcrystals of various organic dyes. , It generally consists in dissolving the organic compound in a hydrophilic solvent, and then pouring a small volume of this concentrated solution into a large volume of water. The organic compound then precipitates, thus leading to the formation of particles in aqueous suspension.…”

Section: Resultsmentioning

confidence: 99%

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Spontaneous Formation of Fluorescent Nanofibers and Reticulated Solid from Berberine Palmitate: A New Example of Aggregation-Induced Emission Enhancement in Organic Ion Pairs

et al. 2011

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The salt formed between the large aromatic berberine cation and the long-chain palmitate anion was synthesized and used to prepare aqueous suspensions of particles owing to a solvent-exchange method. Under these conditions, elongated particles were readily obtained. They were studied by transmission microscopy with polarized light, as well as by fluorescence and electron microscopy. They were shown to be probably crystallized nanofibers, which were stable in suspension. Unexpectedly, upon filtration and drying, these fibers evolved to give a reticulated solid. The fluorescence properties of the compound were analyzed in solution, in aqueous suspension and in the powder crystalline state. Interestingly, berberine palmitate is virtually not fluorescent in aqueous solution because of the quenching effect of water, but transition to the solid state was accompanied by a strong increase in fluorescence intensity. This phenomenon was explained by the original molecular arrangement in the solid state. Actually, in the crystal, the anions form a distinct layer, which limits parallel-stacking of the fluorescent cations. Moreover, the berberine cations are protected from the access of water molecules, and so no quenching effect can take place. This example confirms that the newly introduced concept of ion-pair aggregation-induced fluorescence enhancement can be extended to a variety of structures. It also shows the interest of ion pairs for preparing fluorescent nanofibers and reticulated solids using a solvent-exchange method that is particularly easy to implement.

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Section: Resultsmentioning

confidence: 53%

Section: Resultsmentioning

confidence: 99%

Spontaneous Formation of Fluorescent Nanofibers and Reticulated Solid from Berberine Palmitate: A New Example of Aggregation-Induced Emission Enhancement in Organic Ion Pairs

et al. 2011

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“…However, the presence of aggregates is entirely possible. It was shown recently with methoxycoumarin derivatives that an abundant formation of nanocrystals in a suspension could be unnoticed by routine spectroscopic measurements 37. All of these observations indicate that the DAC moieties undergo constraints in the doubly labeled compounds.…”

Section: Discussionmentioning

confidence: 93%

Interaction of Fluorescently Labeled Triethyleneglycol and Peptide Derivatives with β‐Cyclodextrin

Alouini¹,

Moustoifa²,

Rubio-Albenque³

et al. 2014

ChemPhysChem

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A triethyleneglycol (TEG) chain, a linear peptide, and a cyclic peptide labeled with 7-methoxycoumarin-3-carboxylic acid (MC) and 7-diethylaminocoumarin-3-carboxylic acid (DAC) were used to thoroughly study Förster resonance energy transfer (FRET) in inclusion complexes. (1) H NMR evidence was given for the formation of a 1:1 inclusion complex between β-cyclodextrin (β-CD) and the fluorophore moieties of model compounds. The binding constant was 20 times higher for DAC than for MC derivatives. Molecular modeling provided additional information. The UV/Vis absorption and fluorescence properties were studied and the energy transfer process was quantified. Fluorescence quenching was particularly strong for the peptide derivatives. The presence of β-CDs reduced the FRET efficiency slightly. Dye-labeled peptide derivatives can thus be used to form inclusion complexes with β-CDs and retain most of their FRET properties. This paves the way for their subsequent use in analytical devices that are designed to measure the activity of matrix metalloproteinases.

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Small Iminocoumarin Derivatives as Red Emitters: From Biological Imaging to Highly Photoluminescent Non‐doped Micro‐ and Nanofibres

Khemakhem

Soulié

Brousses

et al. 2015

Chemistry A European J

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The fluorescence properties of four derivatives of 3-thienyl-2-(N-dicyanovinyl)iminocoumarin, bearing a diethylamino group in the 7-position or a methoxy group in the 6, 7 and 8 positions, were compared in solution and in the solid state. The 7-diethylamino derivative was strongly fluorescent in various solvents, with marked solvatochromism. Its fluorescence was quenched by aggregation. In contrast, the methoxy derivatives were only moderately or weakly fluorescent in solution, but two of them were strongly photoluminescent in the crystalline state, owing to favourable molecular packing. The 6-methoxy derivative even exhibited spectacular crystallization-enhanced emission, examples of which are particularly rare for this type of dyes. Dyes were tested for biological use. The 7-diethylamino derivative led to particularly strong fluorescence staining of the cytoplasm of HCT-116 colon cancer cells. No fading was observed over prolonged illumination by the microscope light beam, but a phototoxic effect was detected. The use of the dyes as red-emitting materials was also investigated. Using easy-to-implement preparation methods, the compounds self- assembled to give one-dimensional nano- and microsized particles, including millimeter-long microfibres that exhibited clear wave-guiding properties. This study shows the value of these low molecular-weight molecules for the preparation of new orange and red-emitting fluorescent materials based on totally pure dye.

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Searching for fluorescent nanocrystals in aqueous solutions of 7-methoxycoumarin

Cited by 12 publications

References 32 publications

Spontaneous Formation of Fluorescent Nanofibers and Reticulated Solid from Berberine Palmitate: A New Example of Aggregation-Induced Emission Enhancement in Organic Ion Pairs

Spontaneous Formation of Fluorescent Nanofibers and Reticulated Solid from Berberine Palmitate: A New Example of Aggregation-Induced Emission Enhancement in Organic Ion Pairs

Interaction of Fluorescently Labeled Triethyleneglycol and Peptide Derivatives with β‐Cyclodextrin

Small Iminocoumarin Derivatives as Red Emitters: From Biological Imaging to Highly Photoluminescent Non‐doped Micro‐ and Nanofibres

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