Synthesis of substituted meso-tetraphenylporphyrins in mixed solvent systems

Sun, Zheng; She, Yuanbin; Cao, Ming; Zhou, Qing; Lü, Xingmei; Zhang, Suojiang

doi:10.3998/ark.5550190.p008.097

Cited by 11 publications

(5 citation statements)

References 32 publications

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“…The flexibility and broad scope of the Lindsay method has led to its wide-spread use for porphyrin synthesis, but several challenges remain. Yields remain low due to the presence of multiple competing side reactions, as reported across a wide range of modifications to the method; i.e., the use of ionic liquids (15% yield), [24] Lewis acid catalysts (23% yield), [25] clay catalyst (20% yield), mixed solvent systems (45% yield), [26] microwave synthesis (24% yield), [27] and transition metal ion templating (44% yield) [28] all give yields that are similar to that reported for the original conditions (trifluoroacetic acid, typically 38%) [19].…”

Section: Methodsmentioning

confidence: 99%

Continuous flow synthesis of meso-substituted porphyrins with inline UV-Vis analysis

Parveen,

Morris,

West

et al. 2023

Preprint

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Porphyrin derivatives have found diverse applications due to their attractive photophysical and catalytic properties, but remain challenging to synthesize, particularly at scale. Porphyrin synthesis thus stands to benefit from the more controlled environment, opportunities for efficient optimization, and potential for scale-up available in flow. Here, we have transferred Lindsey porphyrin synthesis into flow, enabling controlled timing for oxidation and neutralization steps and real time monitoring of the reaction mixture with inline UV-Vis analysis. For tetraphenyl porphyrin (TPP), inline UV-Vis showed the presence of protonated TPP, formed due to residual acid catalyst. Thus, inline monitoring allowed optimization of the neutralization step to improve yield. Three further porphyrin substrates were produced in flow; in two cases, the yield from inline UV was significantly higher than the yield from post-purification, identifying further yield losses that could be recovered by modifying the purification step. The workflow presented here can be adapted to multiple substrates to systematically optimise porphyrin yield, reducing the time needed to develop scalable routes to these valuable compounds.

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Section: Methodsmentioning

confidence: 99%

Continuous flow synthesis of meso-substituted porphyrins with inline UV-Vis analysis

Parveen,

Morris,

West

et al. 2023

Preprint

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“…TPP was prepared by the standard Adler-Longo procedure in propionic acid [36] and recrystallized from CH 2 Cl 2 /MeOH. NMR spectra for compounds are in the Supplementary Materials.…”

Section: Methodsmentioning

confidence: 99%

5-Phenyl-10,15,20-Tris(4-sulfonatophenyl)porphyrin: Synthesis, Catalysis, and Structural Studies

2018

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A convenient protocol for the preparation of 5-phenyl-10,15,20-tris(4-sulfonatophenyl)porphyrin, a water-soluble porphyrin with unique aggregation properties, is described. The procedure relies on the one-pot reductive deamination of 5-(4-aminophenyl)-10,15,20-tris(4-sulfonatophenyl)porphyrin, that can be in turn easily obtained from 5,10,15,20-tetraphenylporphyrin by a known three-step sequence involving mononitration, nitro to amine reduction and sulfonation of the phenyl groups. This method provides the title porphyrin in gram scale, and compares very favorably with the up to now only described procedure based on the partial sulfonation of TPP, that involves a long and tedious chromatographic enrichment of the final compound. This has allowed us to study for the first time both the use of its zwitterionic aggregate as a supramolecular catalyst of the aqueous Diels–Alder reaction, and the morphology of the aggregates obtained under optimized experimental conditions by atomic force microscopy and also by transmission electron cryomicroscopy.

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“…The shift that occurs in the Soret band region can also be caused by the energy gap between HOMO and LUMO, which is small due to the presence of a booster group that can increase HOMO and Zn(II) metal ions that enter the porphyrin ring that can decrease LUMO. So that the energy required by the porphyrin ring to absorb energy becomes smaller in the process of electron excitation [20]. This complex compound undergoes a d-d transition, which is indicated by the absorption of wavelengths in the four Q bands.…”

Section: Characterization Of Zn(ii)-tpp Complex Compoundsmentioning

confidence: 99%

“…The Adler method is used in this research's synthesis because it is simple, inexpensive, and does not require pressure under nitrogen [20]. TiO2 is the semiconductor utilized in this study due to its high electron transport capacity, low toxicity, and good chemical stability [21].…”

Section: Introductionmentioning

confidence: 99%

Performance of complex compound Zn-TPP (5,10,15,20-tetrafenylporphyrin) as a dye sensitizer in increasing the current and voltage of dye sensitized solar cells

Darmokoesoemo,

Murwani,

Meirmaziza

et al. 2024

IOP Conf. Ser.: Earth Environ. Sci.

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Solar cell technology has been widely used, one of them is Dye Sensitized Solar Cell (DSSC), which is a semiconductor device that can convert sunlight into electrical energy. The objective of this research is to learn the character of metal complexes from derivatives porphyrin Zn-TPP (5,10,15,20-tetraphenylporphyrin) and apply it as a dye sensitizer in DSSC. Zn(II)-TPP complex compound showed a maximum wavelength at 423 nm on the Soret band. Zn-N bond formed between metal and ligand is indicated at 324,04 cm-1. Zn (II)-TPP complex compound is ionic and best used in DSSC applications. The performance (efficiency) of Zn (II)-TPP complex as dye sensitizer in DSSC shows a maximum current of 8 mA/cm2 with a maximum voltage of 0.60 V and an efficiency value of 9.43%.

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Synthesis of substituted meso-tetraphenylporphyrins in mixed solvent systems

Cited by 11 publications

References 32 publications

Continuous flow synthesis of meso-substituted porphyrins with inline UV-Vis analysis

Continuous flow synthesis of meso-substituted porphyrins with inline UV-Vis analysis

5-Phenyl-10,15,20-Tris(4-sulfonatophenyl)porphyrin: Synthesis, Catalysis, and Structural Studies

Performance of complex compound Zn-TPP (5,10,15,20-tetrafenylporphyrin) as a dye sensitizer in increasing the current and voltage of dye sensitized solar cells

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