Ordered Monolayers of Free-Standing Porphyrins on Gold

The controlled attachment of chromo­phores to metal or semi­conducting surfaces is a prerequisite for the construction of photonic devices and artificial surface-based light-harvesting systems. We present an approach to mount porphyrins in ordered monolayers on Au(111) by self-assembly and verify it...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-08, Vol.136 (32), p.11248-11251
Main Authors: Otte, Franziska L, Lemke, Sonja, Schütt, Christian, Krekiehn, Nicolai R, Jung, Ulrich, Magnussen, Olaf M, Herges, Rainer
Format: Article
Language:English
Subjects:
Adsorption
Dimerization
Gold - chemistry
Materials Testing
Metals - chemistry
Microscopy, Scanning Tunneling
Photons
Porphyrins - chemistry
Quantum Theory
Semiconductors
Spectrophotometry, Ultraviolet
Surface Properties
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Summary:The controlled attachment of chromo­phores to metal or semi­conducting surfaces is a prerequisite for the construction of photonic devices and artificial surface-based light-harvesting systems. We present an approach to mount porphyrins in ordered monolayers on Au(111) by self-assembly and verify it, employing STM, absorption spectroscopy, and quantum chemical calculations. The usual adsorption geometry of planar chromophores, flat on the surface or densely packed edge-on, is prevented by mounting the porphyrins upright on a molecular platform. An ethynyl unit as spacer and pivot joint provides almost free azimuthal rotation of the unsubstituted porphin. However, rotation of the larger tri­phenyl­porphyrin unit is sterically restricted: because the diameter of the substituted porphyrin is larger than the distance to its next neighbors, the phenyl substituents of neigboring molecules interact by dispersion force, which leads to an alignment of the azimuthal rotators.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja505563e