Investigations in the methoxy-iminocoumarin series: Highly efficient photoluminescent dyes and easy preparation of green-emitting crystalline microfibers

Abid-Jarraya, Nihel; Turki-Guermazi, Hamida; Khemakhem, Kacem; Abid, Souhir; Saffon, Nathalie; Fery–Forgues, Suzanne

doi:10.1016/j.dyepig.2013.09.043

Cited by 17 publications

(9 citation statements)

References 25 publications

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“…This behaviour was reminiscent of various coumarin derivatives studied so far in our team 30. However, the spontaneous formation of microfibres, such as those obtained by drop casting with compound 3 , was rarely encountered 12. 13 From a general viewpoint, as far as organic dyes are concerned, micro‐ and nanofibres are usually obtained from compounds that bear extended aromatic moieties associated to large alkyl moieties 31.…”

Section: Resultsmentioning

confidence: 99%

“…[30] However,t he spontaneous formation of microfibres, such as those obtained by drop casting with compound 3,w as rarely encountered. [12,13] From ag eneral viewpoint, as far as organic dyes are concerned,m icro-and nanofibres are usually obtained from compounds that bear extended aromatic moieties associated to large alkyl moieties. [31] Very few low-molecular weight molecules spontaneously assemble to give microfibres and additives such as CTAB may be necessary to increaseanisotropy.…”

Section: Preparation Of Nanofibresmentioning

confidence: 99%

“…Firstly,i nterest in their solidstate emission properties is quite recent. [7][8][9][10][11][12][13] Secondly,t hese small molecules have am oderately extended aromatic system, and so they emit in the blue and green regions.S imple substitutionsa re enough to tune their emission properties within this wavelength range. In contrast, shiftingt he emission spectrum to the red requires ad rastic modification of the conjugated p-electron system, and hence substantial synthetic effort.…”

Section: Introductionmentioning

confidence: 99%

“…The presence of at hiophener ing in the 3-position appeared to promote fluorescence properties in solution. [17] Moreover,a n iminocoumarin derivative bearing am ethoxy group in the 6positionw as shown to give green-emitting crystalline microfibres, and was recently reported as the first example of crystallization-enhanced emission (CEE)i nt his series of dyes, [12] thus pointingo ut the interest of the methoxy group for solid-state fluorescence. These observations, combined with literature data, prompted us to design new fluorophores that bear the thiophene and dicyanovinylamine groups in the 3-and2 -positions, respectively,a sw ell as am ethoxy group on the opposite side of the molecule.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

Section: Preparation Of Nanofibresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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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“…It was reported to exhibit enhanced emission in the solid state, but these properties have not been quantified. In compound 2, a methoxy group was introduced in the 5-position of PBO to slightly strengthen the electron donor character of the benzoxazole unit, and above all because this strongly structuring group may influence the PL properties [11][12][13][14]. A comparison was also made with the hydroxy analogue (3).…”

Section: Introductionmentioning

confidence: 99%

Effect of substitution on the solid-state fluorescence properties of styrylbenzoxazole derivatives with terminal dicyanomethylene group

Brémond¹,

Leygue²,

Jaouhari³

et al. 2021

Journal of Photochemistry and Photobiology A: Chemistry

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Three styrylbenzoxazole derivatives with terminal dicyanomethylene group were studied in order to understand how minor modifications brought to the benzoxazole ring influence the photoluminescence properties. The three compounds were weakly fluorescent in organic solution because of molecular motions around the styryl single bonds. The unsubstituted (1) and methoxy (2) derivatives showed clear solid-state luminescence enhancement (SLE) properties. Distinct emission characteristics were attributed to the formation of amorphous and crystalline particles owing to scanning electron microscopy. These two compounds were also strongly luminescent as microcrystalline powders. Compound 1 that crystallized as slip stacks was a better emitter than the methoxy derivative 2, in which intermolecular interactions are more numerous, according to X-ray diffraction analysis. In contrast, compound 3 was virtually not emissive, confirming that in this series of dyes the presence of the hydroxy group is detrimental to PL emission, as rarely observed among SLE-active fluorophores.

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Aggregation‐Induced Emission: The Whole Is More Brilliant than the Parts

et al. 2014

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"United we stand, divided we fall."--Aesop. Aggregation-induced emission (AIE) refers to a photophysical phenomenon shown by a group of luminogenic materials that are non-emissive when they are dissolved in good solvents as molecules but become highly luminescent when they are clustered in poor solvents or solid state as aggregates. In this Review we summarize the recent progresses made in the area of AIE research. We conduct mechanistic analyses of the AIE processes, unify the restriction of intramolecular motions (RIM) as the main cause for the AIE effects, and derive RIM-based molecular engineering strategies for the design of new AIE luminogens (AIEgens). Typical examples of the newly developed AIEgens and their high-tech applications as optoelectronic materials, chemical sensors and biomedical probes are presented and discussed.

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Investigations in the methoxy-iminocoumarin series: Highly efficient photoluminescent dyes and easy preparation of green-emitting crystalline microfibers

Cited by 17 publications

References 25 publications

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

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

Effect of substitution on the solid-state fluorescence properties of styrylbenzoxazole derivatives with terminal dicyanomethylene group

Aggregation‐Induced Emission: The Whole Is More Brilliant than the Parts

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