Push–Pull Amino Succinimidyl Ester Thiophene‐Based Fluorescent Dyes: Synthesis and Optical Characterization

Sotgiu, Giovanna; Galeotti, Matteo; Samorì, Cristian; Bongini, Alessandro; Mazzanti, Andrea

doi:10.1002/chem.201100142

Cited by 23 publications

(18 citation statements)

References 70 publications

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“…Compounds 1-2 and 7-8 were synthesized by means of the Suzuki cross-coupling reaction 8 in aqueous solvents. Although similar products have already been synthesized in our laboratory by the Stille reaction, 9,10 the Suzuki coupling is by far a better reaction to prepare ultrapure fluorophores. Enabling techniques such as microwave 11 and ultrasound 12 assistance make the preparation rapid (minutes instead of hours) and the yields high.…”

Section: Resultsmentioning

confidence: 99%

Live cell cytoplasm staining and selective labeling of intracellular proteins by non-toxic cell-permeant thiophene fluorophores

et al. 2014

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A structurally correlated series of cell-permeant thiophene fluorophores, characterized by intense green or red fluorescence inside live mouse embryonic fibroblasts, was developed. The fluorophores displayed rapid internalization, excellent retention inside the cells, and high optical stability in the cytosolic environment and did not alter cell viability and reproducibility. Depending on the molecular structure, they experienced distinct fate inside the cells: from bright and lasting staining of the cytoplasm to selective tagging of a small set of globular proteins.

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Section: Resultsmentioning

confidence: 99%

Live cell cytoplasm staining and selective labeling of intracellular proteins by non-toxic cell-permeant thiophene fluorophores

et al. 2014

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“…Design and synthesis of red emitting dyes are gaining interest in recent years [34][35][36][37][38]. The molecules of coumarin class are known to be highly fluorescent [39] with moderate to good quantum yields [40] and are used in biological applications such as fluorescent markers for proteins [41], cellular imaging [42] and lasers [43].…”

Section: Introductionmentioning

confidence: 99%

Red Emitting Coumarins: Insights of Photophysical Properties with DFT Methods

et al. 2015

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Red emitting dyes are of interest in various technological applications. Coumarins, though being an important class of fluorescent molecules, those with red emission, have been rarely studied theoretically. The structural and electronic aspects of three novel red emitting coumarins were studied using DFT and TD-DFT methods. The functionals employed were the hybrid functionals B3LYP, CAM-B3LYP, PBE0 and the highly parameterized empirical functional M06. The geometry at ground state reveals the electron donor N,N-diethylamino group is coplanar with the chromophoric system and the nitrile group induces a red shift to the absorption and emission. The electronic energies and dipole moments were solvent dependent. The basis sets and functionals were benchmarked for their performance with these molecules. B3LYP has been proved to be more efficient in computations whereas the basis sets do not have noticeable effect on the electronic properties. However, adding a polarization function to the basis set has improved the calculation of vertical excitation. The B3LYP functional gives maximum absolute deviation of 0.20 eV in calculating the vertical excitations and 0.18 eV for emission.

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“…The red emitting dyes are of importance in OLEDs to complement their blue and green counterparts, in bio-labelling to achieve greater penetration [10,11] and more cell viability. Design and synthesis of red emitting dyes are gaining interest in recent years [12][13][14][15]. To achieve a red shift in the coumarin molecule there has been a few strategies.…”

Section: Introductionmentioning

confidence: 99%

NLOphoric Red Emitting Bis Coumarins with O-BF2-O core - Synthesis, Photophysical Properties and DFT Studies

Tathe

Sekar

2015

J Fluoresc

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The red emitting dyes were synthesized by employing coumarin core as a donor and boron-bonded coumarin as an acceptor. 7-(N,N-Diethylamino)-coumarin 3-aldehyde was reacted with 3-acetyl-4-hydroxy-coumarin, 7-(N,N-diethylamino)-3-acetyl-4-hydroxy-coumarin and 3-acetyl-4-hydroxy-1-methyl-quinolone to form the corresponding chalcones. The synthesized chalcones were though red shifted as compared to the parent coumarin, and were not emitting in red region. The BF2-complexation was used as a tool to introduce a red shift in the molecules. The BF2-complexes synthesized were found to be red emitting and show higher one photon absorption cross section. The solvatochromism shown by these dyes was studied in the light of solvent polarity parameters. DFT calculations were used to understand the photophysical properties of the synthesized dyes. NLO properties of the dyes were estimated by solvatochromic and computational methods. All the molecules synthesized were characterised with the HRMS and NMR spectral Analysis.

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Push–Pull Amino Succinimidyl Ester Thiophene‐Based Fluorescent Dyes: Synthesis and Optical Characterization

Cited by 23 publications

References 70 publications

Live cell cytoplasm staining and selective labeling of intracellular proteins by non-toxic cell-permeant thiophene fluorophores

Live cell cytoplasm staining and selective labeling of intracellular proteins by non-toxic cell-permeant thiophene fluorophores

Red Emitting Coumarins: Insights of Photophysical Properties with DFT Methods

NLOphoric Red Emitting Bis Coumarins with O-BF2-O core - Synthesis, Photophysical Properties and DFT Studies

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