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Giant Porphyrin Disks: Control of Their Self‐Assembly at Liquid–Solid Interfaces through Metal–Ligand Interactions
Author(s) -
Lensen Marga C.,
Elemans Johannes A. A. W.,
van Dingenen Sandra J. T.,
Gerritsen Jan W.,
Speller Sylvia,
Rowan Alan E.,
Nolte Roeland J. M.
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700131
Subject(s) - porphyrin , highly oriented pyrolytic graphite , crystallography , molecule , ligand (biochemistry) , self assembly , chemistry , intermolecular force , covalent bond , denticity , metal , materials science , scanning tunneling microscope , nanotechnology , photochemistry , organic chemistry , biochemistry , receptor , crystal structure
The synthesis and self‐assembly behaviour of porphyrin dodecamers 1 H 2 and Zn– 1 , which consist of twelve porphyrins that are covalently attached to a central aromatic core, is described. According to STM, 1D and 2D NMR studies, and molecular modelling calculations, the porphyrin dodecamers have a yo‐yo‐shaped structure. Their large π surface, in combination with their disk‐like shape, allows them to form self‐assembled structures, which in the case of Zn– 1 can be tuned by adding bidentate ligands. The self‐assembly of the molecules at the liquid–solid interface of 1‐phenyloctane with highly oriented pyrolytic graphite or Au(111) was imaged by using STM. The porphyrin disks in the self‐assembled arrays have an edge‐on orientation on the surface. The addition of bidentate axial ligands to the Zn –1 molecules in the arrays allows their intermolecular distance to be precisely controlled.