A Dodecameric Porphyrin Wheel

Peng, Xiaobin; Aratani, Naoki; Takagi, Atsuko; Matsumoto, Takuya; Kawai, Tomoji; Hwang, In Wook; Ahn, Tae Kyu; Kim, Dongho; Osuka, Atsuhiro

doi:10.1021/ja0392972

Cited by 126 publications

(79 citation statements)

References 20 publications

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“…In recent years, metal-ligand coordination has been extensively investigated by many organic chemists. 38,39,[135][136][137][138][139][140] The key to coordination-based self-assembly is the ability to manipulate the process of molecular recognition and to generate an enormous variety of rigid framework assemblies featuring well-defined nano-scale cavities. This is a considerable promising approach for the recognition and binding phase of small molecule sensing.…”

Section: Discussionmentioning

confidence: 99%

Molecular Assemblies of Functional Molecules on Gold Electrode Surfaces Studied by Electrochemical Scanning Tunneling Microscopy: Relationship between Function and Adlayer Structures

Yoshimoto

2006

Bulletin of the Chemical Society of Japan

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In this research, molecular assembly and function of aromatic thiols, porphyrins, phthalocyanines, and fullerenes on gold single crystal surfaces was studied by electrochemical methods and scanning tunneling microscopy (STM). Surface functions of promoter molecules such as pyridinethiols, pyrimidinethiols, and benzenethiol for cytochrome c electrochemistry were characterized by electrochemical techniques. Adlayer structures of those molecules were investigated by in situ STM, and molecular orientations for each molecule on the Au surfaces were clarified at molecular level. Adlayers of porphyrins and phthalocyanines for electrocatalytic reduction of dioxygen were examined to elucidate the relationship between activity and adlayer structure. Stable two-dimensional arrays of cobalt porphyrins indicated two-electron reduction of O 2 to H 2 O 2 , whereas two-step four-electron reduction of O 2 to H 2 O occurred because of highly mobile porphyrinatoiron molecules on the surface. Furthermore, well-defined adlayers of crown-substituted phthalocyanine for host-guest interface and binary array consisting of porphyrin and phthalocyanine for the design of supramolecular nanoarchitectures were clearly visualized by STM. Finally, a unique approach for controlling molecular orientation was found by the formation of supramolecular assemblies consisting of porphyrin and fullerene. The electrochemical redox reaction of carbonyl and ferrocene moieties was promoted by using the simple method for the construction of a 1:1 supramolecular assembled film consisting of C 60 derivative and octaethylporphyrinatometal on Au single crystal surfaces.In the field of electrochemistry, surface modification is often used for controlling electron-transfer reactions and catalytic activity. Especially, the electron-transfer reaction of a metalloprotein is currently one of the most active areas in bioelectrochemistry and related fields.

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Section: Discussionmentioning

confidence: 99%

Molecular Assemblies of Functional Molecules on Gold Electrode Surfaces Studied by Electrochemical Scanning Tunneling Microscopy: Relationship between Function and Adlayer Structures

Yoshimoto

2006

Bulletin of the Chemical Society of Japan

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“…It has been reported that the hydrodynamic volumes of ring-shaped polymers are generally smaller than the corresponding linear-shaped polymers, even if the molecular weights are the same, because of the rigidity of the ring. 5,6 This should be the same in the present case. Figure 5 shows plots of KSEC vs. log MW for the mononuclear rhenium(I) complexes.…”

Section: Analysis Of Rhenium(i) Multinuclear Diimine Complexesmentioning

confidence: 66%

“…Neutral oligomers and polymers with rhenium(I) diimine, 4 platinum(II) ethynylarene 5 and metal porphyrins 6,7 as repetition units can be analyzed using gel permeation chromatography (GPC) with THF, toluene, and CH3Cl. For polynuclear metal complexes with high positive charge, however, this method cannot be used because such complexes have low solubility in solvents of low polarity.…”

Section: Introductionmentioning

confidence: 99%

Analysis and Isolation of Cationic Rhenium(I) and Ruthenium(II) Multinuclear Complexes Using Size-Exclusion Chromatography

et al. 2006

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Various cationic rhenium(I) and ruthenium(II) mono-and multinuclear complexes were successfully separated by sizeexclusion chromatography (SEC), using a 50:50 (v/v) mixture of methanol and acetonitrile with CH3CO2NH4 as an eluent. The logarithms of the molecular weights were accurately linear in the distribution coefficients: for linear-shaped rhenium(I) multinuclear complexes, log MW = -2.86KSEC + 5.24 (r = -0.990 and n = 15); for ring-shaped rhenium(I) multinuclear complexes, log MW = -2.94KSEC + 5.40 (r = -0.999; n = 5); for bimetallic complexes including ruthenium(II), log MW = -0.40KSEC + 3.37 (r = -0.959; n = 6). This separation method is applicable to the preparativescale separation of cationic multinuclear complexes from a mixture.

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“…Intramolecular cyclization of porphyrin dodecamers to a porphyrin wheel has also been achieved (Peng et al 2004). Classic examples for structural models of the photosynthetic reaction center are the cofacial bisporphyrins or bischlorins (Kalish et al 1998), which model the structural arrangement of the special pair in the reaction center (Brettar et al 2001, Pascard et al 1993, Fletcher and Therien 2002.…”

Section: Light-harvesting Complexes and Reaction Center Modelsmentioning

confidence: 99%

Photochemical Transformations Involving Porphyrins and Phthalocyanines

Sergeeva¹,

Senge²

2012

CRC Handbook of Organic Photochemistry and Photobiology, Third Edition - Two Volume Set

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A Dodecameric Porphyrin Wheel

Abstract: A dodecameric porphyrin wheel was prepared by Ag(I)-promoted intramolecular coupling of a linear porphyrin dodecamer and was observed by scanning tunneling microscopy (STM). Efficient energy hopping along the array was revealed by femtosecond transient anisotropy measurements.

Cited by 126 publications

References 20 publications

Molecular Assemblies of Functional Molecules on Gold Electrode Surfaces Studied by Electrochemical Scanning Tunneling Microscopy: Relationship between Function and Adlayer Structures

Molecular Assemblies of Functional Molecules on Gold Electrode Surfaces Studied by Electrochemical Scanning Tunneling Microscopy: Relationship between Function and Adlayer Structures

Analysis and Isolation of Cationic Rhenium(I) and Ruthenium(II) Multinuclear Complexes Using Size-Exclusion Chromatography

Photochemical Transformations Involving Porphyrins and Phthalocyanines

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