Dynamic combinatorial olefin metathesis: templated synthesis of porphyrin boxes

Gerven, Paul C. M. van; Elemans, Johannes A. A. W.; Gerritsen, Jan W.; Speller, S.; Nolte, Roeland J. M.; Rowan, Alan E.

doi:10.1039/b503619d

Cited by 54 publications

(40 citation statements)

References 32 publications

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“…This is a considerable promising approach for the recognition and binding phase of small molecule sensing. 141,142 However, it is not so easy to directly apply the knowledge of supramolecular chemistry to surfaces. The concepts of solution-based supramolecular chemistry would be appropriately modified to extend supramolecular assembly technique onto substrate.…”

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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“…The interaction between the template and the ringformation building blocks may be manifold: from covalent bonds [12,13] to complexation of ammonium ions [14] or complexation of transition metal ions. [15][16][17] In this work, we have investigated a polyol as template and boronic acids as building blocks for the macrocycle. Boronic acids [18] have been chosen due to their broad potential to be converted into other functionalities.…”

Section: Introductionmentioning

confidence: 99%

Polyols as Templates for the Synthesis of Macrocycles from Boronic Acid Building Blocks

Lüthje¹,

Bornholdt²,

Lüning³

2006

Eur J Org Chem

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“…[39] Suzuki coupling allowed the synthesis of pentamacrocycle with three porphyrin units, [40] while the metathesis reaction, which used the template effect of tetra-meso-pyridylporphyrin, allowed the synthesis of a huge tetraporphyrin macrocycle. [41] All these data clearly demonstrate efficiency and versatility of the catalytic approaches in the porphyrin transformations.…”

Section: Introductionmentioning

confidence: 73%

Transition Metal Catalysis in Porphyrin Modifications

Averin¹,

Yakushev²,

Beletskaya³

2016

MHC

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Dynamic combinatorial olefin metathesis: templated synthesis of porphyrin boxes

Abstract: A porphyrin macrocyclic square is efficiently prepared by a dynamic combinatorial approach to olefin metathesis and shown by scanning tunneling microscopy (STM) to self-assemble into highly ordered arrays on a graphite surface.

Cited by 54 publications

References 32 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

Polyols as Templates for the Synthesis of Macrocycles from Boronic Acid Building Blocks

Transition Metal Catalysis in Porphyrin Modifications

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