167777-26-6

Basic information

• Product Name: 4,4’-(porphyrin-5,15-diyl)bisbenzoic acid
• CAS NO: 167777-26-6
• Molecular Weight: 550.573
• Mol File: 167777-26-6.mol

Chemical Properties

• Boiling Point: 1215.3±65.0 °C(Predicted)
• Density: 1.430±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4,4’-(porphyrin-5,15-diyl)bisbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4’-(porphyrin-5,15-diyl)bisbenzoic acid(167777-26-6)
• EPA Substance Registry System: 4,4’-(porphyrin-5,15-diyl)bisbenzoic acid(167777-26-6)

Safety Data

• Hazardous Substances Data: 167777-26-6(Hazardous Substances Data)

Usage

Uses

Used in Photodynamic Therapy:
4,4’-(porphyrin-5,15-diyl)bisbenzoic acid is used as a photosensitizer for photodynamic therapy, a medical treatment that involves the use of light to activate a drug to kill cells. Its porphyrin-based structure allows for efficient light absorption and energy transfer, making it effective in generating reactive oxygen species that can destroy diseased cells, particularly cancer cells.
Used in Organic Light-Emitting Diodes (OLEDs):
In the electronics industry, 4,4’-(porphyrin-5,15-diyl)bisbenzoic acid is used as a key component in the fabrication of organic light-emitting diodes (OLEDs). Its ability to absorb and emit light efficiently, along with its stability, makes it suitable for creating high-performance OLEDs with improved brightness, color quality, and energy efficiency.
Used in Materials Science:
4,4’-(porphyrin-5,15-diyl)bisbenzoic acid is utilized as a building block in materials science for the creation of new materials with unique properties. Its porphyrin-based structure and benzoic acid attachments provide opportunities for the development of advanced materials with potential applications in areas such as sensors, catalysts, and energy storage devices.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4,4’-(porphyrin-5,15-diyl)bisbenzoic acid is employed as a starting material for the synthesis of novel compounds with potential therapeutic applications. Its versatile chemical structure allows for the introduction of various functional groups and modifications, enabling the development of new drugs with improved efficacy and selectivity for treating various diseases.

Upstream product

• 109-97-7 pyrrole 
• 50-00-0 formaldehyd 
• 619-66-9 4-Carboxybenzaldehyde 
• 1571-08-0 methyl 4-formylbenzoate 
• 6287-86-1 p-ethoxycarbonylbenzaldehyde 
• 21211-65-4 di(pyrrol-2-yl)methane 

Relevant articles and documents

The influence of triphenylamine as a donor group on Zn-porphyrin for dye sensitized solar cell applications

Two donor-π-acceptor type dyes, Zn[10,20-(4-carboxyphenyl)porphyrin] (Ko-1) and Zn[5,15-diphenylaminophenyl-10,20-(4-carboxyphenyl)porphyrin] (Ko-2), with two different donor units were designed and synthesized for solar cell applications. TheKo-2dye contains the triphenylamine group as an electron donor group, the porphyrin unit acts as a π-bridge, and the carboxylic acid group acts as an anchoring group (electron acceptor unit). TheKo-2dye has a red-shifted absorption maxima owing to the introduction of the dimethylaminophenyl moiety at themesoposition of the porphyrin ring. The highly conjugated dimethylaminophenyl group efficiently donates electrons and the electronic interaction between the porphyrin and dimethylaminophenyl unit is better compared to hydrogen. A dye sensitized solar cell (DSSC) was made using commercial P25 TiO2material as a photoanode, the Zn-porphyrin derivatives as sensitizers, I?/I3?as an electrolyte, and platinum (Pt) as the counter electrode. The molar extinction coefficient, highest occupied molecular orbital (HOMO), and lowest unoccupied molecular orbital (LUMO) values of theKo-2dye are 1.73 × 105M?1cm?1, ?5.82 eV, and ?3.35 eV, respectively, which are more suitable for DSSC applications than those of theKo-1dye, which were 1.31 × 105M?1cm?1, ?6.16 eV, and ?3.60 eV, respectively. The solar cell performance of theKo-2-based DSSC reached 3.3% efficiency with an open circuit voltage (Voc) of 0.68 V, a short circuit photocurrent density (Jsc) of 9.69 mA cm?2, and a fill factor (FF) of 0.49; theKo-1-based DSSC reached 1.90% efficiency, aVocof 0.67 V, aJscof 5.51 mA cm?2, and a FF of 0.54 under AM 1.5 G irradiation.

Synthesis of new TiO2/porphyrin-based composites and photocatalytic studies on methylene blue degradation

In this study, we synthesized porphyrin dyes and structurally characterized them using 1H and 13C NMR and FT-IR and high-resolution mass spectrometry. By using these porphyrins, new TiO2-porphyrin catalysts (TiO2/sub

Nanoscale metal-organic framework for highly effective photodynamic therapy of resistant head and neck cancer

Photodynamic therapy (PDT) is an effective anticancer procedure that relies on tumor localization of a photosensitizer followed by light activation to generate cytotoxic reactive oxygen species (e.g., 1O2). Here we report the rational design of a Hf-porphyrin nanoscale metal-organic framework, DBP-UiO, as an exceptionally effective photosensitizer for PDT of resistant head and neck cancer. DBP-UiO efficiently generates 1O2 owing to site isolation of porphyrin ligands, enhanced intersystem crossing by heavy Hf centers, and facile 1O2 diffusion through porous DBP-UiO nanoplates. Consequently, DBP-UiO displayed greatly enhanced PDT efficacy both in vitro and in vivo, leading to complete tumor eradication in half of the mice receiving a single DBP-UiO dose and a single light exposure. NMOFs thus represent a new class of highly potent PDT agents and hold great promise in treating resistant cancers in the clinic.

Modular Synthesis of trans-A2B2-Porphyrins with Terminal Esters: Systematically Extending the Scope of Linear Linkers for Porphyrin-Based MOFs

Differently functionalized porphyrin linkers represent the key compounds for the syntheses of new porphyrin-based metal–organic frameworks (MOFs), which have gathered great interest within the last two decades. Herein we report the synthesis of a large range of 5,15-bis(4-ethoxycarbonylphenyl)porphyrin derivatives, through Suzuki and Sonogashira cross-coupling reactions of an easily accessible corresponding meso-dibrominated trans-A2B2-porphyrin with commercially available boronic acids or terminal alkynes. The resulting porphyrins were fully characterized through NMR, MS, and IR spectroscopy and systematically investigated through UV/Vis absorption. Finally, selected structures were saponified to the corresponding carboxylic acids and subsequently proven to be suitable for the synthesis of surface-anchored MOF thin films.

Efficient Electrocatalytic Proton Reduction with Carbon Nanotube-Supported Metal-Organic Frameworks

Hydrogen production from Earth-abundant catalysts remains an important but difficult challenge. Here we report the growth of Hf12-porphyrin metal-organic frameworks (MOFs) on carbon nanotubes (CNTs) for electrocatalytic proton reduction. Covale

NANOPARTICLES FOR PHOTODYNAMIC THERAPY, X-RAY INDUCED PHOTODYNAMIC THERAPY, RADIOTHERAPY, CHEMOTHERAPY, IMMUNOTHERAPY, AND ANY COMBINATION THEREOF

Metal-organic frameworks (MOFs) comprising photosensitizers are described. The MOFs can also include moieties capable of absorbing X- rays and/or scintillation. Optionally, the photosensitizer or a derivative thereof can form a bridging ligand of the MOF. Further optionally, the MOF can comprise inorganic nanoparticles in the cavities or channels of the MOF or can be used in combination with an inorganic nanoparticle. Also described are methods of using MOFs and/or inorganic nanoparticles in photodynamic therapy or in X-ray induced photodynamic therapy, either with or without the co-administration of one or more immunotherapeutic agent and/or one or more chemotherapeutic agent.

Strong and directed association of porphyrins and iron(terpyridine)s using hydrogen bonding and ion pairing

The combination of cooperative hydrogen bonding and ion pairing between cationic iron(II)terpyridines and anionic porphyrins yielded remarkably stable neutral complexes even in the highly competitive solvent DMSO. Isothermal titration calorimetry (ITC) was used to compare association constants, enthalpies and entropies of binding between various combinations of the two molecular components that make up the complexes. Steady-state luminescence studies highlighted that, as expected, the fluorescence quenching of the porphyrin is maximized in the cases where the iron(terpyridine) is strapped the tightest across the macrocycle.