22112-87-4

Usage

Uses

Used in Photodynamic Therapy for Cancer Treatment:
5,10,15,20-tetra-2-thienyl-Porphine is used as a photosensitizer for photodynamic therapy, a non-invasive cancer treatment method. Its ability to absorb light and generate reactive oxygen species upon light irradiation makes it effective in inducing cell death in cancerous tissues, while minimizing damage to surrounding healthy cells.
Used in Organic Semiconductors and Materials for Optical and Electronic Devices:
5,10,15,20-tetra-2-thienyl-Porphine is utilized as a key component in the development of organic semiconductors and materials for various applications in the fields of optics and electronics. Its unique molecular structure and properties, such as light absorption and charge transport capabilities, make it a promising candidate for creating advanced materials with improved performance in devices like solar cells, light-emitting diodes, and field-effect transistors.
Used in Chemical Research:
In the field of chemistry, 5,10,15,20-tetra-2-thienyl-Porphine is employed as a model compound for studying the properties and behavior of porphyrin-based systems. Its unique structure allows researchers to investigate the effects of thienyl substitution on the electronic, optical, and redox properties of porphyrins, providing valuable insights into the design and synthesis of novel porphyrin derivatives with tailored properties for specific applications.
Used in Biological Research:
5,10,15,20-tetra-2-thienyl-Porphine is also used in biological research to explore its interactions with biological systems, such as its binding affinity to heme proteins and its potential use as a fluorescent probe for studying protein structure and function. Its unique optical properties make it a valuable tool for investigating biological processes and mechanisms at the molecular level.
Used in Materials Science:
In materials science, 5,10,15,20-tetra-2-thienyl-Porphine is employed in the development of novel materials with enhanced properties for various applications. Its incorporation into polymers, nanoparticles, and other composite materials can lead to the creation of materials with improved electrical conductivity, light-harvesting capabilities, and other desirable characteristics, opening up new possibilities for technological advancements in areas such as energy conversion, sensing, and information processing.

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 109-97-7 pyrrole 
• 645420-44-6 furan-2,5-diylbis(thien-2-ylmethanol) 
• 645420-42-4 2,5-bis[2-thienyl(hydroxy)methyl]thiophene 
• 4521-33-9 5-nitro-2-thiophenecarboxaldehyde 

Relevant academic research and scientific papers

Nitrothienylporphyrins: Synthesis, crystal structure and, the effect of position and number of nitro groups on the spectral and electrochemical properties

This article describes the investigation on the effect of orientation of the meso thienyl groups of porphyrins in deciding the site of nitration. The thienyl rings present at the meso position is found to be more susceptible for electrophilic nitration reaction than the pyrrole β-position in the molecules where there is a better conjugation between the thienyl rings and the porphyrin π-system. Signal corresponding to the imino hydrogens in the proton NMR spectrum of meso nitrothienylporphyrins get shifted to upfield with increase in the number of nitro groups on the porphyrin. This is also due to the extended conjugation of the porphyrins π-system with the meso thienyl rings. The above observations are also supported by the redox potentials of those compounds.

Photophysicochemical properties and photodynamic therapy activity of chloroindium(III) tetraarylporphyrins and their gold nanoparticle conjugates

Novel chloroindium(III) complexes of tetra(4-methylthiophenyl)porphyrin (2a) and tetra-2-Thienylporphyrin (2b) dyes have been synthesized and characterized. The main goal of the project was to identify fully symmetric porphyrin dyes with Q-band regions th

Synthesis and Structural Characterization of meso-Thienyl Core-Modified Porphyrins

A series of meso-thienyl-substituted porphyrins with different porphyrin cores such as N3S, N2S2 and N3O were synthesized and characterized. The thienyl groups at the meso-carbon atoms change the electronic properties of the porphyrin ring. The X-ray structure solved for the N2S2 porphyrin with four meso-thienyl groups showed supramolecular assembly formation in the solid state due to C-H...N hydrogen bonding between the CH group of the meso-thienyl group of one porphyrin ring with the pyrrole N atom of another porphyrin ring. The X-ray analysis of the N3S porphyrin with two mesothienyl groups and two meso-aryl groups did not show any supramolecular assembly formation in the solid state. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Porphyrin compound, preparation method thereof, and application thereof in secondary battery positive electrode material

The invention discloses a porphyrin compound, a preparation method thereof, and an application thereof in a secondary battery positive electrode material. According to the invention, different activefunctional groups are introduced into a porphyrin structural unit, and the porphyrin molecular structure contains multiple active sites, so that the porphyrin molecular structure has ultrahigh theoretical specific capacity, discharge voltage and power density as an electrode active material. The porphyrin compound disclosed by the invention is stable in structure, good in thermal stability, commonand easily available in materials and low in production cost. When the porphyrin compound is applied to an alkali metal ion battery or an alkaline-earth metal ion battery, the result shows that the obtained battery has good specific discharge capacity and excellent cycling stability, excellent energy density and power density. The compound has potential application value in the field of electrochemical energy storage.

Gallium porphyrin axial functionalized graphene oxide multi-element nano hybrid material, and preparation method and application thereof

The invention discloses a gallium porphyrin axial functionalized graphene oxide multi-element nano hybrid material, and a preparation method and application thereof. The multi-element nano hybrid material is prepared by modifying graphene oxide through ax

Electronic and conformational features of derivatives of meso-thien-2-ylporphyrins on protonation and perbromination

The effect of substituents at the meso-position on the electronic and stereochemical properties of thienylporphyrins has been investigated by analyzing the spectra of series of porphyrins. The role of conformation in dictating the extent of electronic pro

Chemical transformations and photophysical properties of meso-tetrathienyl-substituted porphyrin derivatives

The chemistry of meso-tetrathienyl-substituted porphyrin derivatives was explored, including synthesis and subsequent metalation, nitration and 1,3-dipolar cycloaddition reactions. Mono- and tetra-nitro-meso- tetrathienylporphyrins were prepared selectively under mild nitration conditions with NaNO2 and trifluoroacetic acid, and the corresponding chlorins and bacteriochlorins were also obtained by reaction with 1,3-dipoles. The products were characterized in detail and their preliminary photophysical properties were evaluated. Copyright

Synthesis and pharmacological screening of novel meso-substituted porphyrin analogs

A novel series of mesotetrakis[aryl]-21H,23H-porphyrin derivatives 2a-j was synthesized from the condensation of aldehyde derivatives 1a-j with pyrrole in the presence of p-toluenesulfonic acid. The synthesized porphyrins were considered as a model to stu

Effects of substituents on the photophysical properties of symmetrical porphyrins

Porphyrin compounds having groups that mimic the phenolic moiety of m- and p-isomers of 5,10,15,20-tetrakis(hydroxyphenyl) porphyrin (THPP) have been synthesized along with 5,10,15,20-tetrakis(heteroaryl) porphyrins bearing 2-thienyl and 5-thiazolyl groups. Absorption and fluorescence spectroscopy, including fluorescence lifetime (τf) and quantum yield (Φf) measurements, were employed to characterize the singlet excited state of all compounds, using 5,10,15,20-tetraphenylporphyrin (H 2TPP) as a standard (Φf = 0.12 in DMF). The generation of singlet oxygen by each porphyrin photosensitizer was measured as the singlet oxygen quantum yield (ΦΔ), using H2TPP as a standard (ΦΔ = 0.64 in DMF). Partition coefficients were determined using 2-octanol as the organic phase and PBS solution as the aqueous phase. Fluorescence quantum yields ranged from 0.01 to 0.18 for all compounds, with heteroaryl porphyrins having the lowest values. Singlet oxygen quantum yields ranged from 0.40 to 0.65, with heteroaryl porphyrins having the highest values, showing them to be better sensitizers than m- and p-THPP. Log P values were all >1 showing higher solubility in the 2-octanol layer.

Synthesis of 3,4-diarylpyrroles and conversion into dodecaarylporphyrins; a new approach to porphyrins with altered redox potentials

3,4-Diarylpyrroles (1) have been directly prepared in 20-50% yield by the reaction of β-nitrostyrenes with aqueous TiCl3 in 1,4-dioxane. Pyrroles 1 were also prepared via Barton-Zard pyrrole synthesis using the reaction of α-nitrostilbenes with ethyl isocyanoacetate followed by de-ethoxycarbonylation. 3,4-Diarylpyrroles have been converted into dodecaarylporphyrins by reaction with aromatic aldehydes. Various aryl groups are readily introduced at the periphery of porphyrins by this method. Phenyl substitution at any of the positions of pyrroles decreases E1/2ox while E1/2red is almost unchanged. On the other hand, substitution of the 2-thienyl group affects both the HOMO and LUMO energies, and the UV-vis spectra of dodeca-2-thienylporphyrins (4f or 4i) are extremely red-shifted.