Organic Fluorescent Nanofibers and Sub-Micrometer Rods

Fery–Forgues, Suzanne; Fournier‐Noël, Clara

doi:10.5772/8164

Cited by 8 publications

(13 citation statements)

References 99 publications

(104 reference statements)

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“…For instance, the first two members of the series must be selected if the aim is to obtain microfibers for use as active components in microsystems or for the authentication of precious documents. [37][38][39][40] With regard to nanoparticles, the smallest and most stable ones can be obtained using the compounds whose alkyl chain comprises between four and eight carbon atoms. The biological behavior of the compounds also depends on the chain length.…”

Section: Resultsmentioning

confidence: 99%

Conjugates of Benzoxazole and GFP Chromophore with Aggregation‐Induced Enhanced Emission: Influence of the Chain Length on the Formation of Particles and on the Dye Uptake by Living Cells

Carayon

Ghodbane

Gibot

et al. 2016

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Six conjugates of benzoxazole and green fluorescent protein chromophore that differ by the length of their alkyl chain (from C1 to C16) are investigated. They exhibit rigidofluorochromism and clear aggregation-induced emission enhancement (AIEE) behavior with emission in the orange-red that is specific to the solid state. A preparation method based on solvent exchange is used to prepare particles. The self-association properties of these molecules depend on the length of the alkyl chain. Microfibers, platelets, and rounded microparticles are successively obtained by increasing the chain length. The same method is used to prepare nanoparticles (NPs) that are fully characterized. In particular, homogeneous populations of stable NPs measuring around 70 nm are obtained with the analogs whose chains contain four to eight carbon atoms. The behavior with respect to living cells is also influenced by the nature of the compounds. Only the dyes with intermediate hydrophobicity are efficiently uptaken by both normal and tumor cells, and fluorescence only originates from dispersed dye molecules. There is no evidence for incorporation of NPs into cells. This work shows that small variations of the chemical structure must be taken into account for making the best use of AIEE compounds in view of precise applications.

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Section: Resultsmentioning

confidence: 99%

Conjugates of Benzoxazole and GFP Chromophore with Aggregation‐Induced Enhanced Emission: Influence of the Chain Length on the Formation of Particles and on the Dye Uptake by Living Cells

Carayon

Ghodbane

Gibot

et al. 2016

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“…Various types of fluorescent nanofibers exist, based on polymers, peptides, and DNA or made of small organic molecules that are more or less prone to self-organization according to their structure, as already said above. To our knowledge, the present case is the first example of fluorescent nanofibers obtained from an organic salt, in which the fluorophore is associated with an oppositely charged aliphatic moiety.…”

Section: Discussionmentioning

confidence: 99%

“…In particular, nanofibers are of high demand for miniaturized optoelectronic devices where they could be used as active components to generate or transmit light. 1,2 However, the preparation of these nanomaterials is still quite delicate. On the one hand, they must be homogeneous in size, deprived of defects, and prepared in sufficient amount with relatively low costs.…”

Section: ' Introductionmentioning

confidence: 99%

“…Because of the recent development of microtechnologies, the design and preparation of nano- and microsized luminescent materials made of crystallized organic dyes is becoming of acute interest. In particular, nanofibers are of high demand for miniaturized optoelectronic devices where they could be used as active components to generate or transmit light. , However, the preparation of these nanomaterials is still quite delicate. On the one hand, they must be homogeneous in size, deprived of defects, and prepared in sufficient amount with relatively low costs.…”

Section: Introductionmentioning

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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“…(vi) Finally, some recrystallized 2-phenyl-benzoxazole derivatives give acicular crystals, and it is interesting to see if this tendency will be retained in microparticles. Straightforward access to nanofibers could be of high interest for subsequent applications …”

Section: Introductionmentioning

confidence: 99%

Facile Access to Highly Fluorescent Nanofibers and Microcrystals via Reprecipitation of 2-Phenyl-benzoxazole Derivatives

Ghodbane¹,

D’Altério²,

Saffon³

et al. 2011

Langmuir

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2-Phenyl-benzoxazole and five derivatives bearing an alkyl or alkoxy substituent on the phenyl ring were used to prepare aqueous suspensions of particles via a solvent-exchange method. In these conditions, the methyl and methoxy derivatives spontaneously gave nanofibers, while the other compounds led to microcrystals. This shows that minor chemical changes are enough to direct the formation of a given type of particle. From a spectroscopic viewpoint, all compounds strongly emit blue light in the solid state, with spectra much broader than those registered in n-heptane and ethanol solutions. The photoluminescence quantum yields reached 38% and were slightly affected in aqueous suspension by the polarity of the environment. The molecular arrangement, deduced from X-ray analysis for the methyl and methoxy derivatives, was used to explain the fluorescence properties in the solid state. This work shows that 2-phenyl-benzoxazole derivatives are interesting candidates for applications as fluorescent nanomaterials, including in aqueous and biological media.

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Organic Fluorescent Nanofibers and Sub-Micrometer Rods

Cited by 8 publications

References 99 publications

Conjugates of Benzoxazole and GFP Chromophore with Aggregation‐Induced Enhanced Emission: Influence of the Chain Length on the Formation of Particles and on the Dye Uptake by Living Cells

Conjugates of Benzoxazole and GFP Chromophore with Aggregation‐Induced Enhanced Emission: Influence of the Chain Length on the Formation of Particles and on the Dye Uptake by Living Cells

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

Facile Access to Highly Fluorescent Nanofibers and Microcrystals via Reprecipitation of 2-Phenyl-benzoxazole Derivatives

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