- Synthesis of meso substituted porphyrins in air without solvents or catalysts
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meso-Tetraarylporphyrins are synthesized from pyrrole and aryl aldehydes cleanly and efficiently in one step without solvents or catalysts by reactions at temperatures 10-15°C above the boiling point of the starting aldehydes using air as oxidant.
- Drain, Charles M.,Gong, Xianchang
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- Synthesis of new azido porphyrins and their reactivity in copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction with alkynes
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We report herein the preparation of two novel porphyrins substituted with an azido group born either on the para-position of one phenyl meso-susbtituent of a tetraaryl zinc porphyrin (1) or directly on the meso-position of a trisaryl nickel porphyrin (2).
- Séverac, Marjorie,Pleux, Lo?c Le,Scarpaci, Annabelle,Blart, Errol,Odobel, Fabrice
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- Photocatalytic CO2 Reduction Mediated by Electron Transfer via the Excited Triplet State of Zn(II) Porphyrin
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A porphyrin/rhenium complex dyad, ZnP-phen=Re, in which the 2-position of the 1,10-phenanthroline (phen) of fac-Re(phen)(CO)3Br is directly connected with the meso-position of zinc(II) porphyrin, showed phosphorescence from the zinc porphyrin part under Ar, even at room temperature. The phosphorescence was efficiently quenched by 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole (BIH) used as an electron donor, under Ar, with the Stern-Volmer constant KSV = 180a?000 M-1, indicating that the quantitative photoinduced electron transfer occurred from BIH to the excited triplet state (T1) of ZnP-phen=Re. The system affords CO with a high turnover number (>1300) and >99.9% CO selectivity in the photocatalytic CO2 reduction.
- Kuramochi, Yusuke,Fujisawa, Yoshitaka,Satake, Akiharu
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- Design and synthesis of porphyrins bearing rigid hydrogen bonding motifs: Highly versatile building blocks for self-assembly of polymers and discrete arrays
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Two aldehydes, 2,6-diacetamido-4-formylpyridine (7) and 1-butyl-6-formyluracil (11), are used to synthesize five pyridyl and four uracyl meso-subsituted porphyrins. With these complementary porphyrin building blocks, it is possible to build various types of multi-porphyrin supramolecules with different spatial relationships in predefined geometries. The formation and properties of self-complementary dimers and a dosed tetrameric square are presented as a basis of comparison to the latter system in the solid state. An X-ray structure of 5,10-bis(4-tert-butylphenyl)-15,20-bis-(3,5-diacetamido-4-pyridyl)porphyrin confirms its molecular structure and reveals a hydrogen-bonded supramolecular organization mediated by water molecules.
- Shi,Barkigia,Fajer,Drain
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- Oxidative Cyclodehydrogenation Reactions with Tetraarylporphyrins
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The extension of the aromatic π-system of porphyrins is a powerful method to alter their optoelectronic properties. Herein, aryl substituents were fused to porphyrin cores by Scholl oxidation reactions that selectively produced mono- and doubly-fused porphyrins in yields of up to 69 %. Several different aryl substituents attached to the porphyrin were investigated with respect to their reactivity under Scholl conditions. The fused products were fully characterized, i.e., by UV/Vis absorption spectroscopy, which showed drastic changes in the electronic features. Insight into the solid-state behavior was obtained by X-ray crystallography. Our approach represents a novel option for the late-stage functionalization of porphyrin-based compounds.
- Hampel, Frank,Jux, Norbert,Martin, Max M.,Oleszak, Christoph
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supporting information
p. 6758 - 6762
(2020/11/23)
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- PHOTOSENSITIVE RESIN COMPOSITION AND PHOTOSENSITIVE RESIN LAYER USING THE SAME, ADHESIVE COMPOSITION AND ADHESIVE FILM USING THE SAME, COLOR FILTER, POLARIZING PLATE AND OPTICAL DISPLAY DEVICE
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The present invention is related to a photosensitive resin composition and an adhesive composition including a compound represented by Chemical Formula 1, a photosensitive resin layer and an adhesive film manufactured using the composition, a color filter
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Paragraph 0187-0188
(2020/02/18)
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- Formation Reaction and Chemical Structure of a Novel Supramolecular Triad Based on Cobalt(II) 5,10,15,20-(Tetra-4-Tert-Butylphenyl)-21Н,23Н-Porphyrin and 1-Methyl-2-(Pyridin-4′-Yl)- 3,4-Fullero[60]Pyrrolidine
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Results of chemical kinetic/thermodynamic and spectroscopic studies of the reaction of cobalt(II) 5,10,15,20-(tetra-4-tert-butylphenyl)-21Н,23Н-porphyrin (CoIITBPP) with 1-methyl-2-(pyridin-4′-yl)-3,4- fullero[60]pyrrolidine (PyF) in toluene at
- Bichan,Ovchenkova,Gruzdev,Lomova
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p. 711 - 719
(2018/07/13)
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- Facile synthesis of β-functionalized “push-pull” Zn(II) porphyrins for DSSC applications
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Three new β-substituted “push-pull” Zn(II) porphyrin dyes with various electron donors at meso-positions and cyanoacetic acid as acceptor at β-position have been designed and synthesized. These porphyrins have been characterized by UV-Vis, Fluorescence,
- Prakash, Kamal,Manchanda, Shweta,Sudhakar, Vediappan,Sharma, Nidhi,Sankar, Muniappan,Krishnamoorthy, Kothandam
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- Serial compounds with triptycene as framework and in bridge connection with metalloporphyrin through pyrene tetrone and preparation method therefor
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The invention discloses serial compounds with triptycene as a framework and in bridge connection with metalloporphyrin through pyrene tetrone and a preparation method therefor, and belongs to the photoelectric conversion material field. The compound molec
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Paragraph 0088
(2017/01/31)
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- METHODS AND COMPOSITIONS COMPRISING MACROCYCLES
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The present invention relates generally to methods and compositions comprising macrocycles. In some embodiments, the present invention provides methods for modifying macrocycles comprising a pendant group. In some cases, the pendent group comprises a hydrolyzable group. The present invention also provides methods for metallating a macrocycle using microwave energy, in some embodiments.
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Page/Page column 13
(2011/06/26)
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- MnO2 instead of quinones as selective oxidant of tetrapyrrolic macrocycles
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Porphyrins and chlorins were generated through dehydrogenation of the corresponding porphyrinogen and bacteriochlorin precursors using activated manganese dioxide and focused microwave irradiation. The application of this inexpensive heterogeneous oxidant under microwave heating conditions, instead of the quinones usually employed in conventional methodologies, allowed short reaction times, simple overall work-ups and good yields.
- Nascimento, Bruno F.O.,Rocha Gonsalves, António M.d'A.,Pineiro, Marta
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experimental part
p. 395 - 398
(2010/06/12)
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- Efficient synthesis of hangman porphyrins
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Chemical equation presented A two-step synthetic method has been designed to furnish hangman porphyrins In good yields from easily available starting materials. The use of the microwave Irradiation technique has been found to be valuable for delivering the car boxy lie acid hanging group in a much simplified and less time-consuming basic ester hydrolysis (4 h vs 7 days under harsh acidic conditions). The new route facilitates the synthesis of various hangman porphyrins that previously had limited or no access.
- Dogutan, Dilek K.,Kwabena Bediako,Teets, Thomas S.,Schwalbe, Matthias,Nocera, Daniel G.
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supporting information; experimental part
p. 1036 - 1039
(2010/06/15)
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- Solvent-free synthesis of meso-tetraarylporphyrins in air: Product diversity and yield optimization
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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.
- Nia, Shabnam,Gong, Xianchang,Drain, Charles Michael,Jurow, Matthew,Rizvi, Waqar,Qureshy, Meroz
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scheme or table
p. 621 - 629
(2011/10/11)
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- Synthesis of tetraphenylsubstituted porphyrins by interaction of 5-aryldipyrromethanes with 4-substituted benzaldehydes
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Synthesis of tetraphenyl substituted porphyrins with tert-butyl and methoxycarbonyl groups in meso-aryl radicals is described. It is shown that, during the condensation of dipyrromethanes with substituted benzaldehydes, a rearrangement occurs with the formation of a mixture of isomeric porphyrins. The character of these rearrangements depends on the position of substituents in the starting compounds.
- Rumyantseva,Khabarova,Cheshkov,Fedorova,Mironov
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experimental part
p. 762 - 767
(2009/04/18)
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- Reactions of nitroxides with metalloporphyrin alkyls bearing beta hydrogens: Aliphatic carbon-carbon bond activation by metal centered radicals
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Nitroxide-induced beta-hydrogen atom abstraction and beta-elimination of rhodium porphyrin alkyls have been observed. Rhodium(II) porphyrin radical were proposed intermediates to form first and subsequently reacted via aliphatic carbon-carbon bond activation with alkyl substituted nitroxides to yield rhodium porphyrin alkyl complexes.
- Chan, Kin Shing,Mak, Kin Wah,Tse, Man Kin,Yeung, Siu Kwan,Li, Bao Zhu,Chan, Yun Wai
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p. 399 - 407
(2008/03/18)
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- Synthesis and structural characterisation of the first N-heterocyclic carbene ligand fused to a porphyrin
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The functionalisation of two neighboring β-pyrrolic positions of a porphyrin by a fused N-heterocyclic carbene ligand, the subsequent metallation of this external coordination site by palladium(ii) and the structural characterisation of the resulting comp
- Richeter, Sebastien,Hadj-Aissa, Aurelie,Taffin, Celine,Van Der Lee, Arie,Leclercq, Dominique
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p. 2148 - 2150
(2008/02/09)
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- Microwave-assisted synthesis and reverse saturable absorption of phthalocyanines and porphyrins
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Soluble phthalocyanines, including tetrakis(2,9,16,23-cumylphenoxy) copper phthalocyanines (CuPc(β-CP)4), tetrakis(1,8,15, 22-cumylphenoxy) copper phthalocyanines (CuPc(α-CP)4) as well as tetrakis(2,9,16,23- tert -butyl) copper phthalocyanines (CuPc(β-t-butyl)4), and porphyrins (5,10,15,20-tetrakis (4- tert -butylphenyl)porphyrins; M(TBP), M=H2, Zn, Cu, Mg, InCl, AlCl) have been quickly synthesized by microwave irradiation. Furthermore, their reverse saturable absorption have also been investigated by dissolving them in solvent or incorporating them in polymer-silica hybrid material with a sol-gel process with polyvinyl butyral and tetraethyl orthosilicate as precursors. A new method for the preparation process of phthalocyanines and porphyrins in the solids has been successfully used.
- Liu, Mark O.,Tai, Chia-Hon,Wang, Wei-Ya,Chen, Jun-Rong,Hu, Andrew Teh,Wei, Tai-Huei
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p. 1078 - 1084
(2007/10/03)
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- o-(bromomethyl)-substituted tetraarylporphyrin building blocks
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matrix presented A series of novel poly-o-(bromomethyl)ated tetraarylporphyrins was synthesized. Their usefulness as building blocks for porphyrinic materials is demonstrated.
- Jux, Norbert
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p. 2129 - 2132
(2007/10/03)
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- Synthesis, spectroscopy, and semiempirical study of a novel porphyrin- flavin dyad
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A new synthetic methodology for the preparation of donor-bridge-acceptor compounds incorporating a porphyrin donor and an all-aromatic oligo(diazaphenylene) bridge is introduced. This approach allows the controlled preparation of photosynthetic model compounds with well-defined spacer structure and properties. The synthesis of the porphyrin-flavin dyads 1a-c is described to exemplify the strategy. This type of structure has a number of interesting spectroscopic and photophysical properties. The aromatic bridge results in a well-defined donor-acceptor distance; it can favor conjugation and at the same time be nonabsorbing in the visible and near-UV range. The choice of a flavin as the acceptor unit opens the way to a spectroscopic study by excitation of the acceptor in addition to the usual porphyrin donor excitation. Based on these premises, a spectroscopic, photophysical and semiempirical study of the dyad 1 a has been performed in three solvents of varying polarity. The results demonstrate energy transfer from flavin to porphyrin with unit efficiency at high solvent polarity. In solvents of medium polarity an additional internal conversion pathway is opened following excitation of the flavin moiety. Spectroscopic, cyclovoltammetric, and semiempirical results all suggest that this pathway involves the intermediate population of a short-lived charge-separated state.
- Hermann, Dominik T.,Schindler, Anne Christina,Polborn, Kurt,Gompper, Rudolf,Stark, Susanne,Parusel, Andreas B. J.,Grabner, Gottfried,Koehler, Gottfried
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p. 3208 - 3220
(2007/10/03)
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