Molecular engineered silica surfaces with an assembled anthracene monolayer as a fluorescent sensor for organic copper(II) salts

Lu, Fu-Hsing; Gao, Lining; Li, Huihui; Ding, Liping; Fang, Yu

doi:10.1016/j.apsusc.2006.09.038

“…Hence, the major non‐radiative decay route for macrocycles corresponds to the one involving intersystem crossing (ISC) . A similar reduction of fluorescence emission has been previously reported for Cu(II)‐ porphyrin complexes …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin and (Zn²⁺, Mn²⁺, Sn²⁺, Ni²⁺, Al³⁺, V³⁺)‐Derivatives: Photophysical and DFT study

Espitia-Almeida

¹

,

Díaz‐Uribe

²

,

Vallejo

³

et al. 2019

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A novel family of porphyrins based on 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin (1) and six metallo‐derivatives (Zn2+(2), Sn2+(3), Mn2+ (4), Ni2+ (5), Al3+ (6) and V3+ (7)) were synthesized via the Alder‐cols method (synthesis yield between 59%‐75%) and characterized through 1H‐ and 13C‐ NMR, MALDI‐TOF mass spectrometry and FT‐IR assay. Photophysical study was carried out by UV‐Vis and fluorescence spectrophotometry with the aim of assessing their potential as dye sensitizers for photodynamic therapy (PDT). In this regard, fluorescence quantum yield values are between 0.002‐0.38, being the macrocycle 3, the porphyrin with the highest fluorescence quantum yield while the derivative 7 showed the lowest value. Quantum chemical calculations were carried out to study the molecular structure of the porphyrins and to get insight of the luminescent process for 1, which is the free metal system and 3 which includes Sn2+ as metal center. Results indicated that the emissive states involve the transitions with LLCT character for 1, while for 3 it is ML–LCT. This fact evidenced the metal effects on their photophysical properties. Finally, optical and spectroscopic properties and besides, DFT study suggest that 3 could be used as sensitizer in photodynamic therapy applications.

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“…The field of research on new substances with challenging properties in medicine and pharmacology is an important topic, which has become more relevant due to the appearance of resistant and emerging microorganisms. [74][75][76] The compounds (1) and (2) have been used to evaluate their effects on the viability of L. panamensis using the MTT method. The results are presented as cell viability of L. panamensis after exposure to different concentrations of ( 1) and (2) during incubation periods of 24, 48 and 72 hours, in darkness and under irradiation.…”

Section: Electrochemical Characterizationmentioning

confidence: 99%

Photophysical study and in vitro approach against Leishmania panamensis of dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV)

Espitia-Almeida

¹

,

Díaz‐Uribe

²

,

Vallejo

³

et al. 2021

F1000Res

0

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Background: Photodynamic therapy activity against different biological systems has been reported for porphyrins. Porphyrin modifications through peripheral groups and/or by metal insertion inside the ring are main alternatives for the improvement of its photo-physical properties. In this study, we synthesized and characterized 5,10,15,20-tetrakis(4-bromophenyl)porphyrin and the dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV). Methods: Metal-free porphyrin was synthesized using the Alder method, while the Sn(IV)-porphyrin complex was prepared by combining metal-free porphyrin with stannous chloride in DMF; the reaction yields were 47% and 64% respectively. Metal-free porphyrin was characterized by UV-Vis, FT-IR, ESI-mass spectrometry and 13C-NMR. Additionally, the Sn(IV) -porphyrin complex was characterized using UV-Vis and FT-IR. Cyclic voltammetry tests in four different solvents. The fluorescence quantum yield (Φf) was measured using fluorescein as a standard, the singlet oxygen quantum yield (ΦD) was estimated using the standard 5,10,15,20-(tetraphenyl)porphyrin (H2TPP) and the quencher of singlet oxygen 1,3-diphenylisobenzofuran (DPBF). Results: UV-Vis assay showed typical Q and Soret bands for porphyrin and its metallo-porphyrin complex. Compounds showed photoluminescence at the visible range of electromagnetic spectrum. The inclusion of the metal in the porphyrin core changed the Φf from 0.15 to 0.05 and the ΦD increased from 0.55 to 0.59. Finally, the effect of the compounds on the viability of L. panamensis was evaluated by means of the MTT test. The results showed that both compounds decreased the viability of the parasite; this inhibitory activity was greater under light irradiation; the porphyrin compound had IC50 of 16.5 μM and the Sn(IV)-porphyrin complex had IC50 of 19.2 μM. Conclusion: The compounds were synthesized efficiently, their characterization was carried out by different spectroscopy techniques and their own signals were evidenced for both structures, both compounds decreased the cell viability of L. panamensis.

show abstract

“…The field of research on new substances with challenging properties in medicine and pharmacology is an important topic, which has become more relevant due to the appearance of resistant and emerging microorganisms. [74][75][76] The compounds (1) and ( 2) have been used to evaluate their effects on the viability of L. panamensis using the MTT method. The results are presented as cell viability of L. panamensis after exposure to different concentrations of ( 1) and ( 2) during incubation periods of 24, 48 and 72 hours, in darkness and under irradiation.…”

Section: Electrochemical Characterizationmentioning

confidence: 99%

Photophysical study and in vitro approach against Leishmania panamensis of dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV)

Espitia-Almeida

¹

,

Díaz‐Uribe

²

,

Vallejo

³

et al. 2021

F1000Res

3

0

View full text Add to dashboard Cite

Background: Photodynamic therapy activity against different biological systems has been reported for porphyrins. Porphyrin modifications through peripheral groups and/or by metal insertion inside the ring are main alternatives for the improvement of its photo-physical properties. In this study, we synthesized and characterized 5,10,15,20-tetrakis(4-bromophenyl)porphyrin and the dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV). Methods: Metal-free porphyrin was synthesized using the Alder method, while the Sn(IV)-porphyrin complex was prepared by combining metal-free porphyrin with stannous chloride in DMF; the reaction yields were 47% and 64% respectively. Metal-free porphyrin was characterized by UV-Vis, FT-IR, ESI-mass spectrometry and 13C-NMR. Additionally, the Sn(IV) -porphyrin complex was characterized using UV-Vis and FT-IR. Cyclic voltammetry tests in four different solvents. The fluorescence quantum yield (Φf) was measured using fluorescein as a standard, the singlet oxygen quantum yield (ΦD) was estimated using the standard 5,10,15,20-(tetraphenyl)porphyrin (H2TPP) and the quencher of singlet oxygen 1,3-diphenylisobenzofuran (DPBF). Results: UV-Vis assay showed typical Q and Soret bands for porphyrin and its metallo-porphyrin complex. Compounds showed photoluminescence at the visible range of electromagnetic spectrum. The inclusion of the metal in the porphyrin core changed the Φf from 0.15 to 0.05 and the ΦD increased from 0.55 to 0.59. Finally, the effect of the compounds on the viability of L. panamensis was evaluated by means of the MTT test. The results showed that both compounds decreased the viability of the parasite; this inhibitory activity was greater under light irradiation; the porphyrin compound had IC50 of 16.5 μM and the Sn(IV)-porphyrin complex had IC50 of 19.2 μM. Conclusion: The compounds were synthesized efficiently, their characterization was carried out by different spectroscopy techniques and their own signals were evidenced for both structures, both compounds decreased the cell viability of L. panamensis.

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Molecular engineered silica surfaces with an assembled anthracene monolayer as a fluorescent sensor for organic copper(II) salts

Cited by 35 publications

References 43 publications

Synthesis and Characterization of 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin and (Zn²⁺, Mn²⁺, Sn²⁺, Ni²⁺, Al³⁺, V³⁺)‐Derivatives: Photophysical and DFT study

Synthesis and Characterization of 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin and (Zn²⁺, Mn²⁺, Sn²⁺, Ni²⁺, Al³⁺, V³⁺)‐Derivatives: Photophysical and DFT study

Photophysical study and in vitro approach against Leishmania panamensis of dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV)

Photophysical study and in vitro approach against Leishmania panamensis of dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV)

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Molecular engineered silica surfaces with an assembled anthracene monolayer as a fluorescent sensor for organic copper(II) salts

Cited by 35 publications

References 43 publications

Synthesis and Characterization of 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin and (Zn2+, Mn2+, Sn2+, Ni2+, Al3+, V3+)‐Derivatives: Photophysical and DFT study

Synthesis and Characterization of 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin and (Zn2+, Mn2+, Sn2+, Ni2+, Al3+, V3+)‐Derivatives: Photophysical and DFT study

Photophysical study and in vitro approach against Leishmania panamensis of dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV)

Photophysical study and in vitro approach against Leishmania panamensis of dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV)

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Synthesis and Characterization of 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin and (Zn²⁺, Mn²⁺, Sn²⁺, Ni²⁺, Al³⁺, V³⁺)‐Derivatives: Photophysical and DFT study

Synthesis and Characterization of 5,10,15,20‐Tetrakis(4‐ethylphenyl)porphyrin and (Zn²⁺, Mn²⁺, Sn²⁺, Ni²⁺, Al³⁺, V³⁺)‐Derivatives: Photophysical and DFT study