57450-61-0Relevant academic research and scientific papers
Multi-component supramolecular gels induce protonation of a porphyrin exciplex to achieve improved collective optical properties for effective photocatalytic hydrogen generation
Feng, Xuenan,Jiang, Jianzhuang,Lin, Chenxiang,Wang, Tianyu,Yang, Gengxiang
, p. 527 - 530 (2020)
Towards mimicking natural photosystems, supramolecular gels containing two types of porphyrins were developed for photocatalysis. Protonation and J-aggregation of porphyrins within gels expand the absorption to a wide range of visible wavelengths. Porphyrin exciplex formation renders a smaller bandgap for photo-induced electron generation. These features induce effective photocatalytic hydrogen generation.
Enhanced photodynamic therapy through supramolecular photosensitizers with an adamantyl-functionalized porphyrin and a cyclodextrin dimer
Xia, Lei,Wu, Jian,Huang, Baoxuan,Gao, Yun,Tian, Jia,Zhang, Weian
supporting information, p. 11134 - 11137 (2020/10/05)
A supramolecular photosensitizer was constructed using a tetra-adamantane-functionalized porphyrin and a dimer of permethyl-β-cyclodextrin through host-guest interaction and self-assembly. The porphyrin/cyclodextrin alternating structure of supramolecular
Porphyrin-Based Probe for Simultaneous Detection of Interface Acidity and Polarity during Lipid-Phase Transition of Vesicles
Majumder, Rini,Roy, Snigdha,Okamoto, Kentaro,Nagao, Satoshi,Matsuo, Takashi,Parui, Partha Pratim
, p. 426 - 434 (2020/01/09)
Biochemical activities at a membrane interface are affected by local pH/polarity related to membrane lipid properties including lipid dynamics. pH and polarity at the interface are two highly interdependent parameters, depending on various locations from the water-exposed outer surface to the less polar inner surface. The optical response of common pH or polarity probes is affected by both the local pH and polarity; therefore, estimation of these values using two separate probes localized at different interface depths can be erroneous. To estimate interface pH and polarity at an identical interface depth, we synthesized a glucose-pendant porphyrin (GPP) molecule for simultaneous pH and polarity detection by a single optical probe. pH-induced protonation equilibrium and polarity-dependent π-πstacking aggregation for GPP are exploited to measure pH and polarity changes at the 1,2-dimyristoyl-sn-glycero-3-phospho-(1′-rac-glycerol) (DMPG) membrane interface during DMPG phase transition. An NMR study confirmed that GPP is located at the interface Stern layer of DMPG large unilamellar vesicle (LUV). Using UV-vis absorption studies with an adapted analysis protocol, we estimated interface pH, or its deviation from the bulk phase value (ΔpH), and the interface polarity simultaneously using the same spectra for sodium dodecyl sulfate micelle and DMPG LUV. During temperature-dependent gel to liquid-crystalline phase transition of DMPG, there was ～0.5 unit increase in ΔpH from approximately -0.6 to -1.1, with a small increase in the interface dielectric constant from ～60 to 63. A series of spectroscopic data indicate the utility of GPP for evaluation of local pH/polarity change during lipid phase transition of vesicles.
Photodynamic effect of meso-(aryl)porphyrins and meso-(1-methyl-4-pyridinium)porphyrins on HaCaT keratinocytes
Slomp, Amanda M.,Barreira, Sandra M.W.,Carrenho, Luise Z.B.,Vandresen, Camila C.,Zattoni, Ingrid F.,Ló, Stephanie M.S.,Dallagnol, Juliana C.C.,Ducatti, Diogo R.B.,Orsato, Alexandre,Duarte, M. Eugênia R.,Noseda, Miguel D.,Otuki, Michel F.,Gon?alves, Alan G.
supporting information, p. 156 - 161 (2016/12/27)
Sixteen porphyrins, including neutral, anionic and cationic meso-(aryl)porphyrins and meso-(1-methyl-4-pyridinium)porphyrins were herein evaluated in terms of their photosensitizing properties against HaCaT keratinocytes. After an initial screening, the cationic porphyrins were studied in more details, by both determining their log POWand performing PDT assays in lower porphyrin concentrations. Porphyrins presenting two or more adjacent positively charged groups, directly linked to the macrocycle meso positions, appeared to be the most effective photosensitizers. The present study also included the dicationic 5,10-diphenyl-15,20-di(1-methylpyridinium-4-yl)porphyrin (14b), which has previously shown promising results on a psoriasis-like in vivo model. Overall results indicated that the beneficial effect related to porphyrins on psoriasis can be related to the decreasing of keratinocyte viability. Furthermore, some of the cationic porphyrins studied appeared as candidates to be utilized as photosensitizers for psoriasis treatment.
Effects of substituents on the photophysical properties of symmetrical porphyrins
Ormond, Alexandra B.,Freeman, Harold S.
, p. 440 - 448 (2013/02/23)
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 meso-tetraarylporphyrins using SeO2 as oxidant
Ló, Stephanie M.S.,Ducatti, Diogo R.B.,Duarte, M. Eugênia R.,Barreira, Sandra M.W.,Noseda, Miguel D.,Gonalves, Alan G.
experimental part, p. 1441 - 1443 (2011/06/10)
The oxidative step of the two-step, one-flask synthesis of meso-tetraarylporphyrins is herein conducted with heterogeneous oxidant SeO 2 instead of the usual quinones DDQ or p-chloranil. Evaluation of BF3O(Et)2 or I2 amount for the condensation of the first step combined with the excess of SeO2 defined porphyrin synthesis conditions employing benzaldehydes and pyrrole (or 5-phenyldipyrromethane) as starting materials. The simplicity of the workup, allied with reaction mild conditions, makes this method a good option for the synthesis of this kind of compound.
Solvent-free synthesis of meso-tetraarylporphyrins in air: Product diversity and yield optimization
Nia, Shabnam,Gong, Xianchang,Drain, Charles Michael,Jurow, Matthew,Rizvi, Waqar,Qureshy, Meroz
scheme or table, p. 621 - 629 (2011/10/11)
The scope and optimization of a solvent-free method for the rapid preparation and facile purification of technologically important meso-substituted aryl porphyrins, such as 5,10,15,20-tetraphenylporphyrin is presented. This one-step method involves heating the aromatic aldehyde to ～200°C in a vial fitted with a septum-lined cap, followed by addition of the pyrrole and maintaining the temperature for about 20 minutes. The dioxygen in air serves as the oxidant. Present results show that the addition of benzoic acid as a catalyst improves the yield of 5,10,15,20-tetraphenylporphyrin from 22% to 32% and of para halogenated phenylporphyrins from 10% to ～25%. Herein is also presented an examination of the many factors that influence the yield, the ease of purification, and the ability to scale up the reaction. Since the tarry by-products from this method are much less soluble than in most other synthetic strategies, much less solvent is required for purification; simple extraction is often sufficient. This method can be scaled in the lab to > 300 mg, and provides an attractive route to many meso-substituted porphyrins because of its minimal waste generation in terms of both solvent and chromatography support.
