- Polyether-bridged sexithiophene as a complexation-gated molecular wire for intramolecular photoinduced electron transfer
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The porphyrin-sexithiophene-fullerene triad 2, where the two central thiophene units of the sexithiophene spacer are bridged with a crown-ether-like polyether chain, undergoes efficient intramolecular electron transfer from the photoexcited porphyrin moie
- Oike, Takuro,Kurata, Tomoyuki,Takimiya, Kazuo,Otsubo, Tetsuo,Aso, Yoshio,Zhang, Huimin,Araki, Yasuyuki,Ito, Osamu
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- A Synthetic Strategy for Cofacial Porphyrin-Based Homo- and Heterobimetallic Complexes
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We present a straightforward and generally applicable synthesis route for cofacially linked homo- and heterobimetallic porphyrin complexes. The protocol allows the synthesis of unsymmetrical aryl-based meso-meso as well as β-meso-linked porphyrins. Our method significantly increases the overall yield for the published compound known as o-phenylene-bisporphyrin (OBBP) by a factor of 6.8. Besides the synthesis of 16 novel homobimetallic complexes containing MnIII, FeIII, NiII, CuII, ZnII, and PdII, we achieved the first single-crystal X-ray structure of an unsymmetrical cofacial benzene-linked porphyrin dimer containing both planar-chiral enantiomers of a NiII2 complex. Additionally, this new methodology allows access to heterobimetallic complexes such as the FeIII-NiII containing carbon monoxide dehydrogenase active site analogue. The isolated species were investigated by various techniques, including ion mobility spectrometry, DFT calculations, and UV/Vis spectroscopy. This allowed us to probe the influence of interplane distance on Soret band splitting.
- Schissler, Christoph,Schneider, Erik K.,Felker, Benjamin,Weis, Patrick,Nieger, Martin,Kappes, Manfred M.,Br?se, Stefan
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p. 3047 - 3054
(2021/01/20)
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- Novel Cofacial Porphyrin-Based Homo- and Heterotrimetallic Complexes of Transition Metals
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We present a straightforward and generally applicable synthesis route for cofacially linked homo- and heterotrimetallic trisporphyin complexes. The protocol encompasses synthesising the first aryl-based, trans-o-phenylene trisporphyrin starting from pyrrole and benzaldehyde with an overall yield of 3.6 %. It also allows investigating the respective cis-isomer as the first conformationally restricted planar-chiral trisporphyrin. The free-base ligand was used in subsequent metalation reactions to afford the corresponding homotrimetallic Mn(III)-, Fe(III)-, Ni(II)-, Cu(II)-, Zn(II)- and Pd(II) complexes – additionally, a small adaptation of the protocol resulted in the defined Ni(II)Fe(III)Ni(II) complex in a total yield of 2.3 %. By monitoring Ni(II) insertion into the empty trimeric ligands, we affirmed that the outer porphyrin rings are filled before the internal ring. The molecular species were characterised by 1H NMR, UV-Vis, photoluminescence, IR, MS, CID, and high-resolution IMS measurements.
- Schissler, Christoph,Schneider, Erik K.,Lebedkin, Sergei,Weis, Patrick,Niedner-Schatteburg, Gereon,Kappes, Manfred M.,Br?se, Stefan
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p. 15201 - 15207
(2021/08/23)
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- Central zinc metal-controlled regioselective: meso -bromination of zincated β-silylporphyrins - rapid access to meso,β-dual-functionalized porphyrins
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A convenient method for the preparation of meso,β-dual-functionalized porphyrin was developed. The bromination of zincated β-silylporphyrin with NBS selectively yielded meso-bromo-β-silylporphyrin, whereas, the bromination of free-base β-silylporphyrin selectively yielded β-bromoporphyrin via an ipso-substitution of the silyl group. These meso,β-dual-functionalized porphyrins could be used as multipurpose synthons for fabricating various porphyrin derivatives. This journal is
- Hayashi, Satoshi,Takamatsu, Rina,Takeda, Shiori,Noji, Masahiro,Takanami, Toshikatsu
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supporting information
p. 9791 - 9795
(2021/01/05)
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- Metal-catalyzed direct heteroarylation of C-H (: Meso) bonds in porphyrins: Facile synthesis and photophysical properties of novel meso -heteroaromatic appended porphyrins
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A simple and rapid microwave-assisted synthesis of heteroaromatic appended porphyrins using the Pd/Cu-catalyzed C-C coupling of meso-bromoporphyrins with various five- and six-membered heteroaromatic azoles has been successfully developed. The prepared he
- Khandagale, Santosh B.,Pilania, Meenakshi,Arun,Kumar, Dalip
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p. 2097 - 2104
(2018/03/26)
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- Selective halogenation of CH bonds on porphyrin rings using NaX/H2O2
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The selective oxidative halogenation of CH bonds on porphyrins by halides/H2O2 is achieved. Different activities are observed for the three types of aromatic CH bonds on porphyrin ring: meso-H is halogenated preferentially, the β'-H
- Tian, Mi,Chen, Shi,Sheng, Wenbing,Huang, Hui,Guo, Cancheng
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supporting information
p. 1383 - 1385
(2015/11/17)
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- Atropisomeric chiral probes to study the supramolecular organization in porphyrin self-assemblies
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A noncatalysed nucleophilic aromatic substitution was used to prepare the (bacterio)chlorophyll mimics 2-Zn, 3-Zn, 4-Zn and 5-Zn. The localisation of the two recognition groups on the same side of the porphyrin macrocycles in 2-Zn, 4-Zn and 5-Zn produces, through metal-ligand interactions, oligomers that display both H-and J-type aggregates. These supramolecular architectures were confirmed by the introduction of optically pure atropisomers in 5-Zn, which produces chiral aggregates. The UV/Vis and electronic circular dichroism spectra of all aggregates are used to propose an excitonic splitting mode that would correspond to this dual type of chromophoric self-assembly.
- Chappaz-Gillot, Cyril,Canard, Gabriel,Andreoli, Federico,Vanthuyne, Nicolas,Giorgi, Michel,Naubron, Jean-Valere,Monnier, Valerie,Rosas, Roselyne,Roussel, Christian,Balaban, Teodor Silviu
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p. 6526 - 6536
(2013/01/15)
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- Synthesis and characterization of original N-meso chiral substituted diarylporphyrins
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A first palladium catalyzed cross-coupling amination with chiral auxiliaries at the two meso positions of diarylporphyrins was reported. We noticed that, the non-metallation of porphyrins and steric hinderance of the chiral auxiliary play an essential rol
- Abada, Zahra,Ferrié, Laurent,Akagah, Bernardin,Lormier, Anh Tuan,Figadère, Bruno
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supporting information
p. 6961 - 6964
(2013/01/15)
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- Porphyrin dimers and arrays
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Current applications of porphyrins in medicine and optics, such as photodynamic therapy or nonlinear absorbers, increasingly require the use of far-red absorbing dyes. Modifications of the porphyrin structure to accommodate these conditions can be achieve
- Ryan, Aoife,Gehrold, Andreas,Perusitti, Romain,Pintea, Monica,Fazekas, Marijana,Locos, Oliver B.,Blaikie, Frances,Senge, Mathias O.
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p. 5817 - 5844
(2011/11/29)
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- Synthesis and ligand binding properties of triptycene-linked porphyrin arrays
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Multiporphyrin arrays are a complex class of molecules with numerous potential applications in energy transfer, photomedicine, and light harvesting. We have developed a facile/versatile route to a class of triptycene-linked porphyrin arrays via both Suzuk
- Finnigan, Eimear M.,Rein, Regis,Solladié, Nathalie,Dahms, Katja,G?tz, Daniel C.G.,Bringmann, Gerhard,Senge, Mathias O.
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body text
p. 1126 - 1134
(2011/03/22)
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- Bisporphyrin connected by pyrimidine: Synthesis and photo physical properties
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We report the synthesis of a series of zinc porphyrins conjugated with pyrimidine derivatives. V shaped porphyrin dimer with a pyrimidine central core exhibits a planar geometry according to DFT computational studies, presents an internal charge transfer upon excitation proved by typical solvatochromic behavior and moderate two-photon absorption properties. Such porphyrin conjugates can afford valuable advantages in applications of TPA materials such as in photodynamic therapy and imaging of biological entities.
- Achelle, Sylvain,Saettel, Nicolas,Baldeck, Patrice,Fichou, Marie-Paule Teulade,Maillard, Philippe
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scheme or table
p. 877 - 884
(2011/12/02)
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- The Heck reaction for porphyrin functionalisation: Synthesis of meso-alkenyl monoporphyrins and palladium-catalysed formation of unprecedented meso-β ethene-linked diporphyrins
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Palladium-catalysed coupling of the vinyl derivatives methyl acrylate, styrene and acrylonitrile with 5-bromo-10,15,20-triphenylporphyrin (MTriPPBr; M = 2H, Ni, Zn) and 5,15-dibromo-10,20-bis(3,5-di-tert-butylphenyl)porphyrin (MDAPBr2) produced
- Locos, Oliver B.,Arnold, Dennis P.
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p. 902 - 916
(2007/10/03)
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- Palladium-catalyzed cyanation of porphyrins utilizing cyanoethylzinc bromide as an efficient cyanide ion source
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(Chemical Equation Presented) Palladium-catalyzed cyanation of bromoporphyrins is now realized using cyanoethylzinc bromide as a specific cyanating agent. This new protocol provides an easy access to various cyanated Zn(II) porphyrins, including meso-mono
- Takanami, Toshikatsu,Hayashi, Mikiko,Chijimatsu, Hiroshi,Inoue, Wakaba,Suda, Kohji
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p. 3937 - 3940
(2007/10/03)
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