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Near infrared-absorbing self-encapsulated phthalocyanine-cored polycaprolactone star polymeric nanoparticles J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2024-02-19 Aymen Nabeel Yaseen, Atefeh Emami, Haifa Ben Aziza, Merve Dandan Doganci, Ümit İşci, Ayşe Gül Gürek, Erdinc Doganci, Fabienne Dumoulin
An octahydroxylated photosensitizing Zn phthalocyanine has been used as an initiator in ring-opening polymerization of 𝜀-caprolactone. Three different phthalocyanine-core star polymers have been obtained, with each arm functionalized with either 20, 30, or 40 units. To benefit from the absorption of these polymers in the first near-infrared (NIR) phototherapeutic window, the phthalocyanine cores have
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Bismuth porphyrin anchored reduced graphene oxide nanocomposites as a fascinating photocatalyst for rhodamine B dye degradation J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2024-02-19 Rehana Yasmeen, Gauri Devi Bajju, Haq Nawaz Sheikh
Herein, two porphyrins with bismuth metal incorporated in the porphyrinic core were synthesized having peripheral carboxyl and hydroxyl functional groups. The successful synthesis of free base porphyrin and their bismuth-integrated metalloporphyrins was identified using 1H NMR spectroscopy, UV-visible and Fourier transform infrared (FT-IR). Further, these bismuth porphyrins complexes were doped with
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Structural, photophysical, and electrochemical redox properties of meso-tetrakis(pentafluorophenyl)porphyrins J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2024-02-15 Ankit Kumar Deval, Muniappan Sankar
This study delineates the synthesis and comprehensive characterization of metal complexes of meso-tetrakis(pentafluorophenyl)porphyrin (H2TPF20P, 1) with first-row transition metal ions (M = Mn(III) 2, Fe(III) 3, Co(II) 4, Ni(II) 5, Cu(II) 6, and Zn(II) 7) to elucidate their structural, electronic spectral, and electrochemical redox properties. Co, Ni, Cu and Zn Complexes exhibit planar structure (Δ24
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Liquid crystalline behaviors of porphyrin iron(III) chloride complexes with different alkyl chain lengths J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2024-02-15 Dumrongsak Aryuwananon, Suttinun Phongtamrug, Buncha Pulpoka
Two novel porphyrin liquid crystals were designed and synthesized. Their structures were characterized by NMR, FT-IR, UV-visible, and mass spectroscopies. The liquid crystalline properties were investigated by DSC, POM and XRD analyses. The C12 and C18 alkyl chains porphyrin iron(III) complex (1-2) displayed three liquid crystalline transitions in a wide temperature range. Both long alkyl chain porphyrin
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Photodynamic antimicrobial activities of a series of meso-substituted 2,6-dibrominated 1,3,5,7-tetramethylBODIPY dyes J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2024-01-24 Aviwe K. May, Bokolombe P. Ngoy, John Mack, Tebello Nyokong
The photodynamic antimicrobial chemotherapy (PACT) activities of seven 1,3,5,7-tetramethyl-2,6-dibromoBODIPY dyes with 4-acetamidophenyl (2a), 2-iodophenyl (2b), 3-iodophenyl (2c), 4-iodophenyl (2d), 2-bromophenyl (2e), 5-bromothien-2-yl (2f), and methylphenyl ester (2g) meso-substituents were studied against Staphylococcus aureus through irradiation with a 530 nm Thorlabs M530L3 light emitting diode
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Electrocatalytic oxidation of petroleum, toluene and xylene on the Ni-porphyrin-modified graphite electrode J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-12-22 Arezo Bahrami, Majid Jafarian, Ghodsiyeh Sadat Ferdowsi, Saeed Rayati
In this study, electrochemical oxidation of petroleum was performed for the first time. Since petroleum is a rich source of hydrocarbons, its oxidation and electron production resulting in the production of electricity which is green energy is much more efficient than burning it. Electrochemical oxidation of petroleum with Ni-porphyrin-modified graphite electrode in alkaline media and by cyclic voltammetry
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Structure, acidic properties and the coordination ability of sapphyrin with an unsymmetric substitution system J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-12-08 Yulia B. Ivanova, Svetlana G. Pukhovskaya, Mikhail M. Lukanov, Aleksandr S. Semeikin, Arthur S. Vashurin, Sergey A. Syrbu
Synthesis of unsymmetrically substituted 2,3,7,13,16,17,22,23-octamethyl-8,12-di-n-butylsapphyrin dichloride (H5P2+Cl2) was carried out. The synthesized compound was identified by electron absorption, 1H NMR spectroscopy, and mass spectrometry. The stability of the anionic complex and the acidic properties of H5P2+Cl2 were studied by spectrophotometric titration. The parameters of the electronic absorption
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Bacteriochlorin syntheses – Status, problems, and exploration J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-08-23 Vy-Phuong Tran, Pengzhi Wang, Nobuyuki Matsumoto, Sijia Liu, Haoyu Jing, Phattananawee Nalaoh, Khiem Chau Nguyen, Masahiko Taniguchi, Jonathan S. Lindsey
Bacteriochlorins – Nature’s near-infrared (NIR) chromophores – are distinguished by an intense (𝜀∼105 M−1cm−1) long-wavelength absorption band in the ∼700–1000 nm. The development of routes to prepare synthetic, tailorable bacteriochlorins holds promise for multiple disciplines where NIR-light-promoted photoactivity is of interest. A de novo route to bacteriochlorins equipped with a stabilizing gem-dimethyl
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Pyrrole-contained fused-ring compounds J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-08-07 Zhi-Ao Li, Li-Jun Peng, Xin-Yue Wang, Han-Yuan Gong
Three series of pyrrole-contained fused ring compounds are summarized. In recent years, these compounds attracted wide attention with their special and elegant structures. Furthermore, they have played important roles in new optoelectronic materials and guest receptors due to their excellent photoelectric effects and unique properties with nitrogen atom doping.
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Removal of heavy and toxic metals from wastewater using porphyrin-based covalent-organic frameworks: An emerging Field J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-08-07 Pierre D. Harvey
This mini-review assembles the current advances in the adsorption of heavy elements and toxic metals, namely Cr(VI), Mn(II), Ni(II), Cu(II), Tc(VII), Cd(II), Re(VII), Pt(IV), Au(III), Hg(II), Pb(II), and U(VI), bromate (BrO3−), and iodine (I2) in water, as well as the visible-light-driven heterogeneous photocatalytic reduction of highly harmful metal ions into less hazardous or soluble metallic cations
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A porphyrin-based conjugated microporous polymer as a nanozyme for glucose colorimetric sensing J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-08-04 Qi Liu, Qiqi Sun, Jingshun Shen, Yuming Zhang, Hao Li, Sirong Yu, Yanli Chen, Xiyou Li, Jianzhuang Jiang
The development of peroxidase mimics with enhanced peroxidase-like activity is critical to building a convenient and fast glucose colorimetric sensor. Herein, a porphyrin-based conjugated microporous polymer (FePCMP) was synthesized through a Pd-/CuI catalyzed Sonogashira coupling reaction. The FePCMP exhibited specific and superior POD-like activity evaluated by the fast oxidation of 3,3′,5,5′-tetramethylbenzidine
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Redox-responsive 1D-assembly built from cucurbit[8]uril and a water-soluble metalloporphyrin-based tecton J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-08-07 Shagor Chowdhury, Paul Hennequin, Olivier Cala, Sandrine Denis-Quanquin, Éric Saint-Aman, Denis Frath, Floris Chevallier, Christophe Bucher
A linear porphyrin-based tecton bearing two 4,4′bipyridinium units (viologens) and two monomethyl-ether triethylene glycol-substituted phenyl substituents at the meso positions was synthesized and characterized. The latter was involved in the redox-triggered formation of linear supramolecular assemblies with cucurbit[8]uril (CB[8]) cavitands in aqueous media. The CB[8]-promoted intermolecular π-dimerization
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Distortion effect on the ligation of imidazoles to water-insoluble iron(III) porphyrin J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-07-31 Hirofumi Konno, Yoichi Nonomura, Yasushi Kishimoto
Axial ligands control the various chemical reactions triggered by heme proteins. Thus, studies on the reaction of iron porphyrin with ligands are important for understanding their functions. Here, a spectroscopic investigation was performed to clarify the distortion effect of the porphyrin ring on the ligation of imidazoles (imidazole (Im), 1-methyl- and 2-methylimidazole (1-MeIm and 2-MeIm)) to iron(III)
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Electrochemistry of tri-N-methylpyridyl porphyrins J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-07-28 W. Ryan Osterloh, Tatevik Chilingaryan, Benoit Habermeyer, Céline Frochot, Philippe Arnoux, Roger Guilard, Karl M. Kadish
Trisubstituted porphyrin derivatives [(TriMPyP)M]3+(Cl−)3 (where M = 2H, ZnII or PdII) containing three N-methyl-4-pyridyl (N-MePy+) groups were synthesized and characterized electrochemically and spectroscopically in DMSO containing 0.1 M tetrabutylammonium salts. The effect of specific counter-anions, type of metal ion and number of meso-N-MePy+ groups on the redox behavior and spectroscopic properties
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Porphycene conjugates for biomedical applications J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-07-24 David Sánchez-García
The aim of this review is to offer a brief account of the functionalization of porphycenes for the preparation of conjugates useful as photosensitizers for biomedical applications.
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Sn(IV)-corroles reversibly bind carboxylates in the axial position J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-07-21 Helle Ø. Bak, Paolo Cavigli, Andrew Bond, Theis Brock-Nannestad, Michael Pittelkow, Elisabetta Iengo
We present the synthesis of Sn(IV)-corrole complexes that bind to carboxylate moieties reversibly, via axial ligation. The systems have been predominantly characterized using 1H NMR spectroscopy, X-ray crystallography, and MALDI mass spectrometry. The dynamic nature of the Sn(IV)−O2CR bond has been studied in solution using 2D-NMR spectroscopy.
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Perylenemonoimide-subphthalocyanine derivatives: Synthesis, characterization and photovoltaic performance as non-fullerene acceptors in bulk heterojunction solar cells J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-07-21 Jorge Labella, José García-Calvo, Magaly Ramírez-Como, Josep Pallares, Lluis F. Marsal, Tomás Torres
Imide-based Subphthalocyanines (SubPcs) is gaining momentum as non-fullerene acceptors in organic solar cells (OSCs). Herein we report the synthesis, characterization, and photovoltaic performance of Perylenemonoimide (PMI)-SubPc conjugates in which the PMI is linked to the SubPc core by either alkynes or direct C-C bond. These derivatives are prepared via palladium-catalyzed cross-coupling reactions
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Enhanced photoelectrochemical water oxidation of a BiVO4/tetra(amino)phthalocyanine composite photoanode J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-07-19 M. Shire Sudi, Long Zhao, Yuqin Dou, Xin Yang, Qi Wang, Aijian Wang, Weihua Zhu
We present a method for synthesizing a BiVO4 composite photoanode using electrodeposition on FTO glass and show how the incorporation of tetra(amino)phthalocyanine (TAPC) improves its photoelectrochemical water oxidation properties. The conducted photocatalytic tests show that the incorporation of TAPC improved photocurrent generation, electron-hole generation, and separation as well as the stability
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Primary amines as ligands and linkers in complexes of tripyrrindione radicals J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-07-19 Iva Habenšus, Ameen Ghavam, Clayton J. Curtis, Andrei V. Astashkin, Elisa Tomat
Biopyrrin pigments, which result from the degradation of heme in biological settings, feature three or two pyrrole rings and characteristic pyrrolin-2-one termini. These scaffolds serve as redox-active ligands and electron reservoirs in coordination compounds. Tripyrrin-1,14-dione coordinates divalent transition metals as a dianionic ligand hosting a delocalized radical. Herein, we report the synthesis
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Instability of 9-aminoporphycenes J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-07-19 Idaresit Mbakara, Agnieszka Gajewska, Krzysztof Nawara, Jacek Waluk
9-aminoporphycenes degrade over time, yielding products that emit in a similar spectral region as the parent compounds. This leads to a triple fluorescence pattern, with relative intensities changing with time, solvent, excitation wavelength, and irradiation. The decomposition products were analyzed using chromatography coupled with mass spectrometry, absorption, and emission measurements. The spectra
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Investigating axial ligand impact on pinch-porphyrin peroxidase activity with [bis(o-methylpyridino) (dimethylesterprotoporphyrinato)Fe(III)] chloride J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-07-10 Alejandra Romero-Morán, Samuel Hernández-Anzaldo, Hugo Vazquez-Lima, Yasmi Reyes-Ortega
The synthesis and characterization of a novel hexacoordinated compound as a product of the reaction between chlorodimethylesterprotoprphyrin–Fe(III) 1 and 2–methylpiridine (2–CH3Py) was performed. The [bis(o–methylpyridino)(dimethylesterprotoporphyrinato)Fe(III)] chloride 2 is a compound of the family of the pinch–porphyrins, a model of peroxidase enzymes. We analyzed 2 using UV-Vis, 1H NMR, and EPR
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β-Unsubstituted 5-monoazaporphyrin and its derivatives J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-07-06 Rong Yuan, Le Liu, Bangshao Yin, Ling Xu, Mingbo Zhou, Yutao Rao, Jianxin Song
β-Unsubstituted 5-monoazaporphyrin (MAP) copper complex 10,15,20-tritolyl-5-monoazaporphyrinato copper(II) (Cu-MAP) 3 was synthesized by reaction of 1,19-dibromotetrapyrrane with NaN3-CuI in good yield. Following successive reactions of demetallation, metallation and bromination, the important precursor 3,7-dibromo-10,15,20-tritolyl-5-monoazaporphyrinato nickel(II) (β,β′-dibromo Ni-MAP) 6 was prepared
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Expanding Pnictogen-Assisted Self-Assembly of Disulfide Macrocycles to Include Heteroarenes J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-07-05 Luca J. Zocchi, Willow A. Davis, Lev N. Zakharov, Darren W. Johnson
New routes to the formation of macrocyclic molecules are of high interest to the supramolecular chemistry community and the chemistry community at large. Here we describe the incorporation of heterocyclic core units into discrete macrocycles via the utilization of a pnictogen-assisted self-assembly technique. This method allows for the rapid and efficient formation of discreet macrocyclic units from
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The mechanism of novel potential porphyrin photosensitizer mediated phototherapy in SH-SY5Y cell lines and the effect of TMeQ[6] self-assembly in therapy J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-07-01 Zhouxia Lu, Yan Guo, Conghui Wang, Song Xiao
Porphyrin PSs, possessing high photosensitivity and stability, have widespread use in phototherapy. Furthermore, the use of Q[n]s as a carrier for PSs has contributed to enhancing the efficacy of photodynamic therapy. In the present study, we synthesized 2TMeQ[6]-TPPPA self-assembled compounds, comprising TMeQ[6] and 5, 10, 15, 20-tetra (4-pyridyl, N-propyl ammonia) porphyrin derivatives (TPPPA) (in
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Synthesis, characterization and electrochemistry of mono- and dirhodium(I) meso-diaryl dibenzoporphyrin(2.1.2.1) complexes J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-30 Bentian Xiao, W. Ryan Osterloh, Xiaojuan Lv, Yuanyuan Fang, Daiki Kuzuhara, Naoki Aratani, Hiroko Yamada, Fengxian Qiu, Songlin Xue, Karl M. Kadish
A series of mono- and dirhodium(I) meso-diaryl dibenzoporphyrin(2.1.2.1) complexes containing p-tolyl, phenyl or pentafluorophenyl meso-substiuents were synthesized and characterized as to their electrochemical and spectroscopic properties in organic solvents and the data compared to that for same series of free base dibenzoporphyrins in their neutral and protonated forms. The redox behavior of the
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Watson-Crick hydrogen-bonded macrocycles self-assembled from Z-shaped dinucleoside monomers J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-29 David Serrano-Molina, Marina González-Sánchez, Alberto de Juan, Maria J. Mayoral, David González-Rodríguez
The self-assembly of two lipophilic dinucleoside molecules that have a common structure, comprising a bent “Z-shaped” central block substituted at the edges with complementary G and C nucleobases, are studied in this work by a combination of 1D and 2D NMR experiments, as well as by absorption, fluorescence and circular dichroism measurements as a function of the temperature and the concentration. Watson-Crick
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Synthesis of the new bis-pyridine adduct [TTDPzFe(py)2]⋅2H2O, and its detailed solid state properties examined by its magnetic behavior J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-29 Maria Pia Donzello, Keith S. Murray, Claudio Ercolani
The air-stable hydrated FeII species [TTDPzFe(py)2]⋅2H2O (1; TTDPz = tetrakis(thiadiazole)- porphyrazinato dianion) is reproducibly obtained by reaction of the corresponding unmetalated species [TTDPzH2] with the FeII salt (NH4)2Fe(SO4)2⋅6H2O. Experimental interconnection between the bis-pyridine derivative 1 and the bis-adduct of known crystal structure [TTDPzFe(DMSO)2] (2) and the desolvated complex
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Protein-conjugated iron complexes for catalyzing asymmetric carbene insertions into S-H and Si-H bonds J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-28 Irena Saltsman, Zeev Gross
Demonstrated herein are two conceptually different approaches for enantioselective activation of S-H and Si-H bonds, by using protein-conjugated iron complexes for catalyzing the reactions of carbenoids with either racemic thiol or non-chiral silane to form enantiomerically enriched products. Catalysts examined were native myoglobin and transferrin and the spontaneously formed conjugates of serum albumins
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Synthesis of styrene, phenyl acrylate and allyloxyphenyl-functionalized porphyrins, and preliminary exploration of their utility for assembling multiple porphyrin units J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-27 Rohan Bhimpuria, Kiran Reddy Baddigam, Felix Xu, Jordann A. L. Wells, K. Eszter Borbas
Three free-base and two Zn(II) porphyrins carrying one alkene-substituted meso-aryl group and three solubilizing pentyl groups were prepared via mixed aldehyde-type syntheses. A meso p-allyloxyphenyl porphyrin was obtained via the corresponding 5-(p-allyloxyphenyl) dipyrromethane. The porphyrins were fully characterized using a combination of NMR spectroscopy, high-resolution mass spectrometry, and
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Advances in efficacy enhancement of photosensitizer-mediated photodynamic antimicrobial chemotherapy J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-26 Benard M. Isaiah, Edith K. Amuhaya, Clare I. Muhanji
The fight against pathogenic microorganisms has in recent decades been met with fierce setbacks owing to the antimicrobial resistance phenomenon. Conventional antimicrobials have thus weakened in their effectiveness against microbes, calling for the development of innovative strategies to combat the emerging global health crisis. A promising therapy for filling this gap is photodynamic antimicrobial
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Electrochemical and spectroelectrochemical behavior of methyl pheophorbide a - zinc phthalocyanine dyad J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-26 Ekaterina O. Moiseeva, Stanislav A. Trashin, Irina O. Balashova, Anton D. Kosov, Tatiana V. Dubinina, Victor E. Pushkarev
The electrochemical properties of a covalently linked conjugate (Dyad) composed of methyl pheophorbide a (Pheoa) and zinc(II) 2-(2-hydroxymethylbenzyloxy)-9(10),16(17),23(24)-tri-tert-butylphthalocyaninate (ZnPc) were studied. Cyclic voltammetry (CV) and square wave voltammetry (SWV) measurements revealed three reductions at -1.59, 1.78 and -2.03 V vs. Fc+/Fc and four oxidations at 0.06, 0.47, 0.57
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β-Pyrrole functionalized push-pull BODIPYs: Synthesis, photophysical, electrochemical, thermal and computational studies J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-26 Indresh Singh Yadav, Rajneesh Misra
A series of β-pyrrole functionalized push-pull BODIPYs BDP 1-06 were designed and synthesized via Palladium-catalyzed Suzuki cross-coupling reaction and by increasing the oxidation state of the sulfur atom in the thiazine ring. The effect of various donor entities on the photophysical, electrochemical, thermal, and computational studies of the BODIPY was investigated. The absorption spectra of the
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Synthesis, dark and photoinduced cytotoxicity of a deuteroporphyrin IX derivative with two galactose fragments on the macrocycle periphery J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-26 Tatyana K. Rocheva, Elena S. Belykh, Marina V. Mal’shakova, Yana I. Pylina, Dmitry V. Belykh
A deuteroporphyrin IX derivative with two D-galactose fragments with an ester bond between macrocycle and carbohydrate fragments was synthesized. The synthesis was done by esterifying both ester groups of deuteroporphyrin IX with diacetone-D-galactose using 2-chloro-1-methylpyridinium iodide (Mukayama reagent) followed by the removal of the isopropylidene protection of carbohydrate fragments by the
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Highly NIR-II luminescent erbium porphyrinoids J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-26 Li-Jun Guo, Jun-Long Zhang
Erbium (Er3+) ion exhibits efficient broadband emission at 1.53 μm (4f optical transition 4I13/2 → 4I15/2), which is promising to achieve better clarity and deeper penetration depth for biological imaging. However, because of the relatively low luminescent level (4I13/2, ca. 6500 cm−1) and the tendency of being facile to be quenched by high-energy oscillators such as N-H, C-H, or O-H groups, achieving
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Density functional theory investigation of the coordination of Zn(II)-tetraphenylporphyrin with 1,2,3-triazole ligands J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-23 Jean-François Nierengarten
In this paper, we report density functional theory (DFT) studies to fully understand the coordination interactions between 1,4-disubstituted 1,2,3-triazole derivatives and the metal center of Zn(II)-porphyrins. Coordination through the most electron-rich N3 atom of the triazole heterocycle is more favorable. However, the energy difference between the N2- and N3-coordinated isomers is moderate and the
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Post-synthetic DNA modification with porphyrins for DNA-templated supramolecular assemblies J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-23 Vasilis Nikolaou, James W. Wood, Georgios Charalambidis, Athanassios Coutsolelos, Eugen Stulz
The use of azide-alkyne cycloaddition (“click chemistry”), both Cu-catalysed and Cu-free, was probed to attach different porphyrins onto oligodeoxynucleotides (ODNs), and the efficiency was compared to amide coupling reaction. Terminal attachment using the different methodologies provides porphyrin-ODNs in varying yields, and the porphyrin-ODNs can be transformed into multiporphyrin arrays using DNA-templated
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A porphyrin-based ion pair receptor constructed through click chemistry J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-19 Xiaoyan Dong, Wei Lin, Shuping Wang, Haotian Zhang, Zibin Zhang, Chunsong Xie, Shijun Li
A novel heteroditopic porphyrin-based ion pair receptor with four ureas and four triazoles on the same side of the porphyrin ring was synthesized through click chemistry. This receptor showed high affinity to complex with the ion pairs KCl, NaCl and NH4Cl in 1:1 binding stoichiometries with association constants of 2.48 (± 0.43) × 104, 1.06 (± 0.02) × 105, and 1.97 (± 0.04) × 105 M−1, respectively
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Teaching with Arduino: Porphyrinoids’ fluorescence in olive oil J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-19 Frédéric Bolze
During the pandemic period, we were forced to reconsider teaching of practical labs, as students had mainly to work at home. It was the occasion to explore the use of cheap microcontroller kits for teaching chemistry and to work out some manipulations with household products. Back to normal life, it is important to valorize this equipment and work to design simple chemistry experiments which could
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Electronic properties and redox chemistry of N-confused metalloporphyrins J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-19 Frederico F. Martins, Marcel Swart
Here we study the effect of metals on the characteristic Soret band of N-confused porphyrins. We used DFT calculations to study how this low-lying region of the spectrum of the NCP-2H isomer is affected by the introduction of transition metals with various (d2, d3, d4 and d6) d-electron configurations. The spin ground state of these complexes is mostly dependent on the number of unpaired electrons
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Benzene-crosslinked hexaphyrin: Molecules of benzene in hexaphyrin J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-19 Hidemitsu Uno, Shogo Hata, Kohei Hashimoto, Kota Muramatsu, Hideyuki Nakano, Takahiro Takiue, Hiroki Uoyama, Yuma Tanioka, Shigeki Mori, Tetsuo Okujima, Masayoshi Takase
Two blueish materials were obtained in the acid-catalyzed condensation of 5-pentafluorophenyldipyrromethane-1,9-bis{(petafluorophenyl)-methanol} with 4,8-dihydro-4,8-ethanopyrrol[3,4-f]isoindole followed by oxidation, although the yields were low. Their structures were unambiguously determined by the X-ray analysis. One was ethylene-connected bisdipyrromethene and another was bicyclo[2.2.2]octene-crosslinked
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Osmium ester-hinged chlorin dimers J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-15 Nivedita Chaudhri, Sarina J. Dorazio, Lalith P. Samankumara, Pedro Daddario, Michelle L. Head, Matthias Zeller, Christian Brückner
A bis(dihydroxychlorin) osmate ester is formed as a side product in the osmylation of meso-tetraphenylporphyrin. The product can also be formed in good yield along well-known reaction pathways of osmate esters by treatment of the monomeric chlorin diol osmate ester bispyridine complex with acid. The dimer was spectroscopically characterized. The free base dimer can be metalated with zinc(II). The
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Pd(II)dipyrrinato complexes: Synthesis, crystal structure and their antibacterial applications J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-15 Neha Manav, Jaydeepsinh Chavda, Saqib Kidwai, Ramandeep Singh, Shigeki Mori, Iti Gupta
The synthesis and biological studies of a series of Pd(II)dipyrrinato complexes are reported. The thiogalactosyl and/or oligoethyleneglycol moieties were linked with themeso-aryl rings of the Pd(II)dipyrrinato complexes. The Pd(II)dipyrrinato complexes were characterized by MASS, IR, UV-Vis, and NMR spectroscopic techniques. Single crystal X-ray structure of the homoleptic Pd(II)dipyrrinato complex
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Photochemistry and photocatalysis of transition-metal porphyrin complexes and analogues J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-14 Young Hyun Hong, Yong-Min Lee, Wonwoo Nam, Shunichi Fukuzumi
Although photoexcited state lifetimes of transition-metal porphyrin complexes are usually too short to exhibit any appreciable reactivity in intermolecular redox reactions with substrates, there are several cases to show enough lifetimes of the photoexcited states of transition-metal porphyrins and analogues to be involved in intermolecular photoredox reactions. This minireview focuses on such examples
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Recent developments in corrole radicals J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-14 Hu Gao, Fan Wu, Kai Wang, Zhen Shen
Corrole is a tetrapyrrolic ring-contracted porphyrin analog with one direct pyrrole-pyrrole link. The corrole macrocycle is electron-rich and easily stabilized in its one electron oxidized radical state, especially when coordinated to some specific metal ions. The corrole radicals and their complexes have demonstrated excellent air stability, amphoteric redox properties, and diversified spin configurations
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Nanoarchitectonics of supramolecular porphyrins based on a bis(porphyrin) cleft molecule J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-14 Takehiro Hirao, Takeharu Haino
This account describes the construction of supramolecular constructs based on our bis(porphyrin) cleft molecule. The bis(porphyrin) cleft molecule was originally synthesized as a tweezer-shaped host molecule for planar guest molecules. A detailed study on the bis(porphyrin) cleft molecule revealed that the bis(porphyrin) cleft molecule forms two kinds of supramolecular structures. One structure is
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The influence of central metal in phthalocyanine for photodynamic therapy of glioblastoma J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-14 Ayça Tunçel Oral, A. Celil Yüzer, Derya Özel, Mine Ince, Fatma Yurt
Glioblastoma multiforme (GBM) is an aggressive and fatal brain tumor that tends to occur in older adults and has several subtypes. The fact that the mechanisms of initiation and progression of glioblastoma are not yet known is an obstacle to the treatment of the disease. For this reason, studies have been carried out in recent years to develop new therapeutic approaches. Photodynamic therapy (PDT)
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Phenylboron(III) complexes of tripyrrins: A new class of macrocycles closed by hydrogen-bonding J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-14 Kyo Yamagata, Oscar Fernandez-Vera, Shu Seki, Takayuki Tanaka
Dianilinotripyrrin was condensed with phenylboronic acid at high temperature to give its phenylboron(III) complex in which the conjugation system changed to serve as a divalent ligand. As a result, two aniline moieties form an intramolecular hydrogen bond between the NH and iminic N sites, fixing the conformation to stand as a closed macrocycle. The structure of this macrocycle contains both cone-shaped
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Azacalixphyrin nanostructures J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-14 Daniel Ferry, Sabrina Pricl, Domenico Marson, Zhongrui Chen, Gabriel Canard, Simon Pascal, Aura Tintaru, Olivier Siri
Azacalixphyrins are used as building blocks to elaborate nanostructures with different shapes depending on the nature of the N-substituents. In this work, the formation of nanoribbons from N-alkyl azacalixphyrin 4, and nanodonuts from the N-aryl analogue 5, is presented and rationalized by molecular dynamics (MD) simulations. Indeed, MD revealed different modes of intermolecular interactions (defines
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Visible light-driven borylation of aryl halides by a B12 derivative based on a dual photoredox strategy J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-14 Kaito Sasaki, Keita Shichijo, Mamoru Fujitsuka, Hisashi Shimakoshi
Reductive dehalogenation of an aryl halide (Ar-X) subsequent coupling with bis(pinacolato)diboron (B2pin2) to form an arylboronate (Ar-Bpin) by the photo-excited B12 complex of the CoI oxidation state with an iridium photosensitizer (PS), [Ir(dtbbpy)(ppy)2]PF6, under anaerobic conditions was reported. The robust B12 complex and iridium PS provided the highest turnover numbers of over 3,800 for the
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Synthesis and optical properties of 3,5-bis(10-phenylanthracen-9-yl)benzene-appended porphyrins J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-14 Akane Umemiya, Haruyuki Nakano, Nanami Iwaya, Tadaaki Ikoma, Yoshihiro Matano
Singlet–singlet and triplet-triplet energy-transfer processes between anthracenes and porphyrins have received considerable attention in materials chemistry. Herein, we report the first examples of 3,5-bis(10-phenylanthracen-9-yl)benzene-appended porphyrins (BPABPs) designed to study intramolecular energy transfer between two chromophores. The Curtius rearrangement of 3,5-bis(10-phenylanthracen-9-yl)benzoyl
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Synthesis and aggregation-induced emission properties of α-perimidinyl 3-pyrrolyl BODIPY J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-14 Pinky Chauhan, Kanhu Charan Behera, Mangalampalli Ravikanth
A new dye called the α-perimidinyl 3-pyrrolyl BODIPY(PPyBODIPY) was synthesized readily by treating α-formyl 3-pyrrolyl BODIPY with 1,8-diamino naphthalene in ethanol at reflux. The PPyBODIPY was thoroughly characterized and studied by HR-MS, 1D & 2D NMR, absorption, fluorescence and DFT/TDDFT techniques. The PPyBODIPY absorbs strongly in the 500-600 nm region and emits weakly in the region of 550–650
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Synthesis and characterization of lead metallated non-peripherally substituted octa-octyl tetrabenzo(aza)porphyrins showing face-to-face columnar stacking in the crystal phase J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-14 Lydia Sosa Vargas, Simon J Coles, Graham J Tizzard, Isabelle Chambrier, Michael J Cook, Andrew N Cammidge
The full range of porphyrin-phthalocyanine hybrids can be synthesized by treatment of 1,4-dioctylphthalonitrile with varying equivalents of MeMgBr to produce mixtures favoring specific hybrid structures and the tetrabenzoporphyrin in the extreme case. The individual macrocycles can be isolated in pure form as their magnesium derivatives and subsequently demetallated to give the parent metal-free compounds
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Ethylbenzene oxidation by a hybrid catalysis system of reconstituted myoglobin and silica-protected PdAu nanoparticles under a hydrogen-oxygen mixed atmosphere J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-14 Koji Oohora, Yoshiyuki Kagawa, Yasutaka Kuwahara, Hiromi Yamashita, Takashi Hayashi
C–H bond oxidation using molecular oxygen as a terminal oxidant is an important reaction in molecular conversions. This reaction is achieved by several enzymes such as cytochrome P450s in biological systems, whereas artificial catalytic systems for this reaction are limited. In this work, the oxidation of ethylbenzene was promoted by a hybrid catalysis system consisting of myoglobin reconstituted with
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Investigation of antibacterial photodynamic inactivation in urea-doped TiO2 sensitized with porphyrin photocatalysis J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-06-06 Parisa Nosrati, Rahmatollah Rahimi, Mahboubeh Hosseini-Kharat
Choosing the right photosensitizers (PSs) as well as the right light source is very critical in antimicrobial photodynamic therapy (aPDT). Some light sources, such as ultraviolet, have high cytotoxicity and poor penetration and some PSs are hydrophobic with low solubility in water, and easy aggregation. To address these issues, we modified TiO2 nanoparticles with urea and TCPP (TCPP=tetra(4-carboxyphenyl)
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Identification of mitochondrial proteins associated with cyanine 5 using a combination of affinity-based photocrosslinking with bio-orthogonal supramolecular latching J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-05-31 Jaehwan Sim, Meng Li, Kyeng Min Park, Kimoon Kim
Visualization of mitochondria with cyanine dyes has been exploited to study the functions of mitochondria. However, proteins interacting with cyanine dyes have not been investigated clearly. Here, we report a chemical proteomics approach for the identification of mitochondrial proteins associated with cyanine dyes. This approach uses affinity-based photocrosslinking of Cy5-diazirine-alkyne (Cy5-DAyne)
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Identification of mitochondrial proteins associated with cyanine 5 using a combination of affinity-based photocrosslinking with bio-orthogonal supramolecular latching J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-05-31 Jaehwan Sim, Meng Li, Kyeng Min Park, Kimoon Kim
Visualization of mitochondria with cyanine dyes has been exploited to study the functions of mitochondria. However, proteins interacting with cyanine dyes have not been investigated clearly. Here, we report a chemical proteomics approach for the identification of mitochondrial proteins associated with cyanine dyes. This approach uses affinity-based photocrosslinking of Cy5-diazirine-alkyne (Cy5-DAyne)
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Reductive chemistry of pyrrolic macrocycles: A PCET dichotomy between metal and ligand J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-05-24 Dilek K. Dogutan, Daniel G. Nocera
Proton-coupled electron transfer (PCET) is central to the reactivity of porphyrins. The coupling of the electron to the proton is central to a porphyrin’s ability to catalyze energy conversion reactions of which the hydrogen evolution reaction (HER) is exemplary. To understand the mechanistic details of the PCET chemistry of porphyrins and related macrocyclic congeners, we have designed hangman constructs
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Orthogonal and twisted dimers of redox-active pyrrole-fused pentaazapolycyclic hydrocarbons J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-05-24 Tomoyuki Narita, Kazuki Fujiwara, Hidemitsu Uno, Motoko S. Asano, Tohru Nishinaga, Masayoshi Takase
Orthogonal and twisted dimers of pyrrole-fused pentaazapolycyclic hydrocarbons (pentaazacoronene analogs) were synthesized, linked either directly or by phenylenes. Although the dimers and the reference monomer did not have any substituents at the α-positions of the terminal pyrroles, two reversible oxidation waves were observed in the cyclic voltammograms. ESR measurements of the chemically generated
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Synthesis and photophysical properties of subphthalocyanine substituted with tetraphenylethylene moieties J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-05-12 Taniyuki Furuyama, Sho Shitanda, Tomoteru Fukumura, Nagao Kobayashi
Tetraphenylethylene-substituted phthalonitriles and corresponding subphthalocyanines have been synthesized. Mono- and di-substituted phthalonitriles could be prepared by a typical SNAr reaction. The crystallographic structures of phthalonitriles indicated that intermolecular π-π interactions were suppressed by the bulky tetraphenylethylene moieties. Subphthalocyanines substituted with tetraphenylethylenes
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Stoichiometry-controlled chirality inversion in the amide-linked zinc bisporphyrinates induced by amino acid esters J. Porphyr. Phthalocyanines (IF 1.5) Pub Date : 2023-05-12 Jiaxing Zhu, Fangfang Fu, Zhihao Zhang, Chuanjiang Hu, Yong Wang
We investigated chirality transfer processes with two amide-linked zinc bisporphyrinates as hosts and chiral amino acid esters as guests. The linkers in these hosts contain a coordination site (pyridyl nitrogen or amino nitrogen). CD spectra were measured after titration of these zinc bisporphyrinates with amino acid esters. The CD spectra show that the signals were inverted during the titration. This