- Synthesis and cycloaddition reactions of pyrrole-fused 3-sulfolenes: A new versatile route to tetrabenzoporphyrins
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Pyrrole-fused 3-sulfolenes 2a,b were prepared from the corresponding α,β-unsaturated sulfone 1. These pyrroles undergo thermal extrusion of sulfur dioxide to produce highly reactive o-quinodimethanes which can be trapped in Diels-Alder reactions. The resulting pyrroles are important starting reagents in porphyrin synthesis.
- Vicente, Maria G. H.,Tome, Augusto C.,Walter, Andreas,Cavaleiro, Jose A. S.
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- Synthesis of extremely soluble precursors of tetrabenzoporphyrins
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This paper describes the preparation of dimethylbicyclo[2.2.2]octadiene-fused porphyrins as extremely soluble precursors of tetrabenzoporphyrins and thermal conversion of the precursors to tetrabenzoporphyrins.
- Okujima, Tetsuo,Hashimoto, Yusuke,Jin, Guangnan,Yamada, Hiroko,Uno, Hidemitsu,Ono, Noboru
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- Synthesis and spectral characteristics of (tetrabenzoporphyrinato) chloromanganese(III)
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A method is developed of synthesis of (tetrabenzoporphyrinato) chloromanganese(III) from tetrabenzoporphyrinatocadmium( II) (as a donor of the macrocyclic ligand) and the salts, manganese acetate MnAc2 and dichloromanganese MnCl2, in boiling dimethylformamide in the presence of atmosperic oxygen in 80% yield. It is found that under the conditions of the synthesis tetrabenzoporphyrinatomanganese(II) is formed which can be oxidized by the atmospheric oxygen to (tetrabenzoporphyrinato)chloromanganese(III). Absorption spectra in the visible and infrared regions, R f and the data of elemental analysis characterizing the resulting compound are given.
- Sheinin,Chizhov,Romanova
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- SNAr reactions of β-substituted porphyrins and the synthesis of meso substituted tetrabenzoporphyrins
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Reaction of 2,3,7,8,12,13,17,18-octaethylporphyrin with LiR reagents containing functional groups readily yields meso substituted derivatives suitable for further transformations with residues such as -p-C 6H5Br, -p-C6Hsu
- Senge, Mathias O.,Bischoff, Ines
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- Acid-Responsive Conductive Nanofiber of Tetrabenzoporphyrin Made by Solution Processing
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While cofacial one-dimensional (1-D) π stacking of a planar aromatic molecule is ideal for the construction of conduction systems, such molecules, including tetrabenzoporphyrin (BP), prefer to form edge-to-face stacking through CH-π interactions. We report here that the BP molecules spontaneously form a 1-D cofacial stack in chloroform containing 1% trifluoroacetic acid (TFA) and that a bundle of the formed nanofiber shows acid-responsive 1-D conductivity as high as 1904 S m-1. A small fraction (2.7%) of BP in the fiber exists in a cation radical state, and 1.5 equiv of TFA is located in an intercolumnar void. Dedoping and redoping of TFA with trimethylamine vapor results in 1300-2700-fold decreases and increases, respectively, in the conductivity and also the amount of the radical cation. The conductivity of the fiber also shows a correlation with the pKa of acid dopants.
- Zhen, Yonggang,Inoue, Kento,Wang, Zongrui,Kusamoto, Tetsuro,Nakabayashi, Koji,Ohkoshi, Shin-Ichi,Hu, Wenping,Guo, Yunlong,Harano, Koji,Nakamura, Eiichi
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- Effect of copper metalation of tetrabenzoporphyrin donor material on organic solar cell performance
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The effects of copper metalation of tetrabenzoporphyrin on the properties and performance of organic solar cells are studied. Tetrabenzoporphyrin (BP) and copper tetrabenzoporphyrin (CuBP) are both solution processed from soluble precursor materials and thermally converted in the thin film. Despite high field-effect hole mobility above 1 cm2 V-1 s-1, the power conversion efficiency (PCE) of solar cell devices with CuBP is severely diminished compared to those with BP. Conducting atomic force microscopy (c-AFM) is used to show that CuBP films are highly conductive in the direction perpendicular to the substrate, relative to those comprising BP. By analyzing the donor absorption characteristics as well as the external quantum efficiency and short-circuit current density of bilayer OPV devices as a function of donor layer thickness, it is determined that the differences in performance are likely due to a prohibitively short effective exciton diffusion length (LD) in the metalated derivative. By modeling the external quantum efficiency of bilayer OPV devices, we are able to approximate this difference in effective LD to be 15 nm for BP and 2 nm for CuBP. This journal is the Partner Organisations 2014.
- Guide, Michele,Lin, Jason D. A.,Proctor, Christopher M.,Chen, Jingrun,Garcia-Cervera, Carlos,Nguyen, Thuc-Quyen
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- Columnar structure in bulk heterojunction in solution-processable three-layered p-i-n organic photovoltaic devices using tetrabenzoporphyrin precursor and silylmethyl[60]fullerene
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(Chemical Equation Presented) A new solution-processable fabrication protocol using a soluble tetrabenzoporphyrin (BP) precursor and bis(dimethylphenylsilylmethyl)[60]fullerene (SIMEF) created three-layered p-i-n photovoltaic devices, in which the i-layer possesses a well-defined bulk heterojunction structure in which columnar BP crystals grow vertically from the bottom p-layer. The device showed a power conversion efficiency of 5.2% (V OC = 0.75 V; JSC = 10.5 mA/cm2; FF = 0.65).
- Matsuo, Yutaka,Sato, Yoshiharu,Niinomi, Takaaki,Soga, Iwao,Tanaka, Hideyuki,Nakamura, Eiichi
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- FULLERENE COMPOUND, SEMICONDUCTOR DEVICE, SOLAR CELL AND SOLAR CELL MODULE
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PROBLEM TO BE SOLVED: To provide a new semiconductor material. SOLUTION: The present invention provides a fullerene compound having a structure represented by formula (I). The present invention provides a fullerene compound having 1-5 structure(s) represe
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Paragraph 0162-0163
(2017/05/11)
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- Synthesis and spectral properties of lanthanide double-decker complexes with tetrabenzoporphyrin and phthalocyanine
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Mixed-ligand double-decker complexes containing tetrabenzoporphyrin and phthalocyanine fragments were synthesized by reaction of phthalocyanine dilithium salt with tetrabenzoporphyrin complexes of lutetium, dysprosium, gadolinium, neodymium, and lanthanum. A relation was found between spectral parameters of the obtained sandwich complexes and radii of the central metal ions.
- Galanin, N. E.,Shaposhnikov, G. P.
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p. 851 - 857,7
(2020/08/31)
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- Synthesis of benzoporphyrins with one or two meso-substitutents via substitution reactions
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Reaction of either free base benzoporphyrin, its zinc(II) complex orβ-bicyclo(2,2,2)octeno appended precursor porphyrins with LiR reagents gave an entry into mono- and soluble di-meso-substituted benzoporphyrins.
- Senge, Mathias O.,Bischoff, Ines
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p. 879 - 886
(2007/10/03)
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- Organic semiconductor material and organic electronic device
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An organic semiconductor material comprising a compound which has a generalized porphyrin skeleton and which has a molecular structure such that the distance from the generalized porphyrin ring plane to the center of each atom forming the generalized porp
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- A new synthesis of benzoporphyrins using 4,7-dihydro-4,7-ethano-2H- isoindole as an isoindole equivalent
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Various benzoporphyrins and their metal complexes were obtained in 100% yield by heating porphyrins fused with bicyclo[2.2.2]octadiene at 200 °C. This thermal (retro Dieis-Alder) reaction proceeds very cleanly to give pure benzoporphyrins without further
- Ito, Satoshi,Ochi, Naoyuki,Murashima, Takashi,Uno, Hidemitsu,Ono, Noboru
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p. 399 - 411
(2007/10/03)
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- A new synthesis of benzoporphyrins using 4,7-dihydro-4,7-ethano-2H-isoindole as a synthon of isoindole
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Heating 4,7-dihydro-4,7-ethano-2H-isoindole at 200 °C induces the retro-Diels-Alder reaction to give isoindole in essentially quantitative yield, which can be applied to a new synthesis of tetrabenzoporphyrins and monobenzoporphyrins.
- Ito, Satoshi,Murashima, Takashi,Uno, Hidemitsu,Ono, Noboru
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p. 1661 - 1662
(2007/10/03)
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- Alkyl ether analogues of benzoporphyrin derivatives
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Compounds having properties superior to known photosensitizers defined by the following chemical formula: STR1 including R groups R1, R2, R3, and R4, wherein R1 and R2 are methyl or --CH(O--(CH2)n CH3)CH3 or are joined together to form the group D and wherein R3 and R4 are methyl or --CH(O--(CH2)n CH3)CH3 or are joined together to form the group D; provided that one of R1 and R2 or R3 and R4 are joined together to form the group D wherein one of the remaining R groups is methyl and one of the remaining R groups is --CH(O--(CH2)n CH3)CH3, where n is an integer of 5 through 7 and group D is: STR2 and R5 is independently at each occurrence --OR6 where R6 is lower alkyl of 1 through 7 carbon atoms or R6 is an amino acid residue.
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- Preparation and Spectroscopic Properties of Pure Tetrabenzoporphyrins
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Cadmium tetrabenzoporphyrin, tetrabenzoporphyrin, and the bispyridine complex of magnesium tetrabenzoporphyrin were synthesized.As judged from the visible absorption spectra these compounds are not contaminated with porphyrin-like impurities. 100-MHz 1H Fourier-transform n.m.r. spectra of the above mentioned compounds are presented.From the low-temperature e.s.r. spectra it can be concluded that the lowest triplet state of biligated magnesium tetrabenzoporphyrin exhibits a static Jahn-Teller distortion resulting in a loss of four-fold molecular symmetry.
- Koehorst, Rob B. M.,Kleibeuker, Joop F.,Schaafsma, Tjeerd J.,Bie, Dick A. de,Geurtsen, Bart,et al.
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p. 1005 - 1009
(2007/10/02)
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