Supramolecular architectures of porphyrins on surfaces: The structural evolution from 1D to 2D to 3D to devices

Mohnani, Stefan; Bonifazi, Davide

doi:10.1016/j.ccr.2010.05.006

Cited by 169 publications

(136 citation statements)

References 108 publications

Supporting

Mentioning

134

Contrasting

Unclassified

Order By: Relevance

“…The readers' attention shall also be drawn to existing review articles containing information about porphyrin and phthalocyanine structures in two dimensions: A concise overview of porphyrins at interfaces was given by Auwärter et al [186]. Supramolecular nanostructures of porphyrins on surfaces have been reviewed by Mohnani and Bonifazi [187] and, with particular focus on the co-adsorption with fullerenes, by Yoshimoto and Itaya [4]. Examples of more recent work about porphyrins and fullerenes at solid/liquid and electrochemical interfaces can be found in Refs.…”

Section: Structure Dynamics and Manipulation: Supramolecular Orderinmentioning

confidence: 99%

Surface chemistry of porphyrins and phthalocyanines

Gottfried

2015

Surface Science Reports

571

586

View full text Add to dashboard Cite

Section: Structure Dynamics and Manipulation: Supramolecular Orderinmentioning

confidence: 99%

Surface chemistry of porphyrins and phthalocyanines

Gottfried

2015

Surface Science Reports

571

586

View full text Add to dashboard Cite

“…From the point of view that the orientation of bacteriochlorophylls is associated with strong electronic coupling, the well-organised porphyrin antenna systems with sophisticated three-dimensional structures play central roles to ensure the coverage of solar energy wavelength. In this respect, supramolecular self-assembly is ideally suited for creating well-defined nanostructures as a result of their high specificity and directionality (8)(9)(10)(11). Since the properties of the components largely dominate the function of assembled structures in general, the self-assembled architectures of newly designed porphyrins would constitute a great importance for applications in optical switches, energy conversion devices and nonlinear optical materials (12)(13)(14)(15)(16)(17)(18)(19)(20).…”

Section: Introductionmentioning

confidence: 99%

Supramolecular dimeric structures of pyrazole-containing meso-oxo carbaphlorin analogues

Ishida

Fujimoto

Morimoto

et al. 2016

Supramolecular Chemistry

View full text Add to dashboard Cite

Synthesis and properties of a novel meso-oxo carbaphlorin analogue embedded with an N-free pyrazole moiety are described. The N-benzyl precursor was prepared by a [3 + 1]-MacDonald condensation of N-benzyl pyrazole dialdehyde and β-alkyl-substituted tripyrrane dicarboxylic acid and subsequent oxidation by ferric chloride. Upon deprotection of the benzyl group, the resulting N-free oxophlorin analogue formed a unique supramolecular dimer through mutual hydrogen bonding interactions between the pyrazole NH and meso-carbonyl group. The assembled behaviour was characterised by various spectroscopies, X-ray crystallographic analysis and vapour pressure osmometry. Under the similar reaction conditions, the condensation of meso-phenyl-substituted tripyrrane derivative afforded an unprecedented tetrapyrrolic macrocycle fused with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone unit at their α-pyrrolic positions. The X-ray crystallographic analysis of the macrocycle revealed a twisted core structure, and nonaromatic nature was elucidated.

show abstract

“…Intermolecular electronic communication in their programmed arrays particularly has attracted a lot of interests in a wide range of fields, from photomaterials [8] to pigments, [9] molecular devices, [10] and catalysts.…”

mentioning

confidence: 99%

Switchable Intermolecular Communication in a Four‐Fold Rotaxane

et al. 2011

View full text Add to dashboard Cite

In biological systems, precise intermolecular electronic communication occurs in, and is regulated by, proteins and their complexes. For example, light-harvesting complexes have metal ions or metal complexes, such as manganese clusters, and organic cofactors, such as chlorophylls, carotenoids, or ubiquinones, in the "right" spatial arrangement so that electrons and energy can be efficiently transferred. [1, 2] Electronic communication between molecules is sensitive to their relative orientation. Large molecular scaffolds of proteins provide precise frameworks for molecular arrays as well as the ability of dynamic switching intermolecular communication, accomplished by conformational changes induced by external stimuli. These natural molecular frameworks are programmed as sequences of amino acids, but we could achieve flexible intermolecular communication in a simpler molecular architecture by using mechanically interlocked supramolecular motives, such as catenanes and rotaxanes, in which two or more molecular components are inseparable but their interactions are flexibly convertible. [3,4] Syntheses of rotaxanes have been well-established, and a large variety of fascinating examples of rotaxane-based molecular systems has been reported. [3][4][5] As a specific example of switchable rotaxanes, Stoddart, Credi and co-workers reported elevatorlike motion of a molecule with crown ethers along the strings on another molecule in a three-fold rotaxane, in which the relative position between the molecules was switchable by redox or acid-base reactions.[6] Sauvage and co-workers made a porphyrin dimer in a cyclic [4]rotaxane and showed its ability to act as switchable receptor.[7] Porphyrin, phthalocyanine, and their metal complexes have been applied to a broad range of functionalized molecular systems. Intermolecular electronic communication in their programmed arrays particularly has attracted a lot of interests in a wide range of fields, from photomaterials [8] to pigments, [9] molecular devices, [10] and catalysts.[11]Herein, we report a mechanically linked cofacially stacked dimer of a metalloporphyrin and metallophthalocyanine units by formation of a four-fold rotaxane and its switchable spin-spin communication induced by external stimuli. A rotaxane consisting of a secondary ammonium ion and a crown ether has been recognized as a versatile building block for supramolecular systems. R 2 NH 2 + ions are complexed by dibenzo [24]crown-8 in a threaded manner as a result of electrostatic stabilization and hydrogen bonds between the negatively charged interior of the crown ether and the cationic ammonium moiety.[12] We designed a porphyrin unit with four alkylammonium chains [1·4 H] 4+ and phthalocyanine unit with peripheral crown ethers 2 which are expected to form a facially stacked dimer through formation of a four-fold rotaxane (Figure 1) [13] ) and the phthalocyanine 2 in chloroform and acetone at a ratio of 4:1, followed by locking through Staudinger-phosphite reaction, which converts the azide groups to larger ph...

show abstract

Supramolecular architectures of porphyrins on surfaces: The structural evolution from 1D to 2D to 3D to devices

Cited by 169 publications

References 108 publications

Surface chemistry of porphyrins and phthalocyanines

Surface chemistry of porphyrins and phthalocyanines

Supramolecular dimeric structures of pyrazole-containing meso-oxo carbaphlorin analogues

Switchable Intermolecular Communication in a Four‐Fold Rotaxane

Contact Info

Product

Resources

About