Synthesis, Spectral-Luminescent Properties, and Photostability of Zn(II) Complexes With Dipyrrins Modified by the Periphery and meso-Spacer

Дудина, Н. А.; Nikonova, A. Yu.; Antina, Ye. V.; Berezin, Mikhail Y.; V’yugin, A. I.

doi:10.1007/s10593-014-1426-2

Cited by 16 publications

(3 citation statements)

References 15 publications

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“…Electronic absorption spectrum (λ max , nm (logε)): 508 ( Homoleptic Zn(II) complexes 4-6 were prepared according to Scheme 2 by modified procedure reported in [32]. (4); R = Ph, Х = СН (5); R = Ph, Х = N (6); ROH -is the corresponding alcohol.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, spectral-luminescent properties of B(III) and Zn(II) complexes with alkyl- and aryl-substituted dipyrrins and azadipyrrins

Антина

Berezin

Дудина

et al. 2014

Russ. J. Inorg. Chem.

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Effect of complexing atom, molecular structure of dipyrrolylmethene and its aza analog on spec tral luminescent properties of heteroleptic boron(III) and homoleptic zinc(II) complexes with 3,3',5,5' tet ramethyl 2,2' dipyrrolylmethene, 3,3',5,5' tetraphenyl 2,2' dipyrrolylmethene, and 3,3',5,5' tetraphenyl ms aza 2,2' dipyrrolylmethene in organic solvent solutions was studied. The complexes were found to exhibit strong chromophore (λ = 350-690 nm, ε ~ 10 5 L/mol cm) and fluorescent properties. Quantum yield (γ fl ) for fluoroborate complexes reaches 100% and is weakly dependent on medium nature. The value of γ fl for phenyl and alkyl substituted zinc(II) dipyrrolylmethenates in nonpolar solvents is not higher 0.3 and 0.03, respectively; complete fluorescence quenching is observed in electron donating solvents. Aza substitution at the meso spacer causes considerable shift of electronic absorption and fluorescence spectra to the red region but completely quenches fluorescence of zinc(II) chelates and decreases γ fl of boron(III) complex to 0.04.

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Section: Methodsmentioning

confidence: 99%

Synthesis, spectral-luminescent properties of B(III) and Zn(II) complexes with alkyl- and aryl-substituted dipyrrins and azadipyrrins

Антина

Berezin

Дудина

et al. 2014

Russ. J. Inorg. Chem.

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“…The dipyrrin ligands 1,3,7,9-tetramethyl-5-mesityldipyrromethene 30 and 2,8diiodo-1,3,7,9-tetramethyl-5-mesityldipyrromethene 23 were synthesized according to published procedures. Complexes 1 and 2 were synthesized according to a modified literature procedure, 38 as described below.…”

Section: ■ Introductionmentioning

confidence: 99%

Quantifying Triplet State Formation in Zinc Dipyrrin Complexes

2019

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Photocatalysis is a promising method to harness solar energy and use it to form fuels and other high-value chemicals, but most sensitizers used in photocatalytic reactions are complexes of rare and expensive metals such as ruthenium and iridium. Zinc dipyrromethene complexes have potential to be a more earth-abundant alternative, but their photophysical properties are largely unexplored. In this study, triplet state formation was quantified in two zinc dipyrromethene complexes, with and without heavy atoms, by transient absorption spectroscopy. Without heavy atoms, the triplet quantum yield was 16% in toluene and 27% in THF. With the addition of heavy I atoms, the triplet quantum yield increased to 62−63% and was insensitive to solvent polarity. The fact that in the absence of heavy atoms the triplet yield is affected by solvent polarity and in the presence of heavy atoms it is not suggests that triplet formation occurs through different pathways in the two complexes. These triplet yields meet or exceed those of successful organic photosensitizers, illustrating the potential for zinc dipyrromethene complexes as photosensitizers.

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“…However, the fluorescent Boron derivatives from Schiff bases are sparse in fluorescent probes ( vide infra ) . The bio‐markers should show the following characteristics: able to enter cells, good solubility, biocompatibility, chemo‐, and photo‐stability, high brightness when internalized into cells and minimal cytotoxicity . However, at subcellular level most of the diseases are correlated to irregular levels of cellular pH, viscosity, and oxygen concentration …”

Section: Introductionmentioning

confidence: 99%

Organoboron Schiff bases as cell‐staining fluorescent probes: Synthesis, Chemio‐photophysical characterization, DFT, and X‐ray structures

Ibarra-Rodríguez

Muñoz‐Flores

Gómez-Treviño

et al. 2019

Applied Organom Chemis

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The fluorescence imaging technologies are becoming the most powerful and noninvasive diagnostic tools in cellular biology and modern medicine where abnormal cell arrangements are associated with diseases. Thus, these techniques require new fluorescent dyes with excellent chemical, physical, and photophysical properties. A series of four new Boron Schiff bases (1–4) has been prepared by condensation between phenylboronic acid with the corresponding ligand. The compounds were characterized by NMR (1H, 13C, and 11B), UV/vis, fluorescence spectroscopy, and high‐resolution mass spectrometry. The crystal structures of three compounds showed tetracoordinated Boron atoms with semiplanar skeleton ligands. Interesting organoboron response to viscosity on their fluorescence (Φ: more than 3‐fold). Additionally, compounds 1 and 2 were found to serve as a fluorescent dye for cell imaging (B16F10, CaCo, and A‐431 cells) since it has the capability to rapidly accumulate within the cells and gave bright green fluorescence, it showed low cytotoxicity activity and high photostability in solution. Additionally, the compounds have also been investigated using DFT.

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Synthesis, Spectral-Luminescent Properties, and Photostability of Zn(II) Complexes With Dipyrrins Modified by the Periphery and meso-Spacer

Cited by 16 publications

References 15 publications

Synthesis, spectral-luminescent properties of B(III) and Zn(II) complexes with alkyl- and aryl-substituted dipyrrins and azadipyrrins

Synthesis, spectral-luminescent properties of B(III) and Zn(II) complexes with alkyl- and aryl-substituted dipyrrins and azadipyrrins

Quantifying Triplet State Formation in Zinc Dipyrrin Complexes

Organoboron Schiff bases as cell‐staining fluorescent probes: Synthesis, Chemio‐photophysical characterization, DFT, and X‐ray structures

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