Self-organized monolayer of meso-tetradodecylporphyrin coordinated to Au(111)

Nathalie Katsonis; Javier Vicario; Tibor Kudernac; Johan Visser; Michael M. Pollard; Ben Feringa

doi:10.1021/ja065823o

Self-organized monolayer of meso-tetradodecylporphyrin coordinated to Au(111)

Nathalie Katsonis
, Javier Vicario
, Tibor Kudernac
, Johan Visser
, Michael M. Pollard
, Ben Feringa

Stratingh Institute, University of Groningen

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

The structure of molecular monolayers formed at the interface between atomically flat surfaces and a solution of free-base meso-tetradodecylporphyrins (H2Ps) was examined by scanning tunneling microscopy (STM) at the liquid/solid interface. On the surface of graphite (HOPG), H2Ps form a well-ordered monolayer characterized by an oblique unit cell. On Au(111), H2Ps form a self-organized monolayer comprised of two distinct domain types. In both types of domains, the density of the porphyrin cores is increased in comparison to the arrangement observed on HOPG. Also, high-resolution STM images reveal that, in contrast to what is observed on HOPG, physisorption on Au(111) induces a distortion of the porphyrin macrocycle out of planarity. By using X-ray photoelectron spectroscopy, we demonstrate that this is likely to be due to the coordination of the lone pairs of the iminic (−CN−) nitrogen atoms of the porphyrin macrocycle to Au(111).

Original language	English
Pages (from-to)	15537 - 15541
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	128
Issue number	48
DOIs	https://doi.org/10.1021/ja065823o
Publication status	Published - 1 Nov 2006
Externally published	Yes

Keywords

molecular monolayers
structure
meso-tetradodecylporphyrins
scanning tunneling microscopy

Access to Document

10.1021/ja065823o

7 Article

Third-Generation Light-Driven Symmetric Molecular Motors
Kistemaker, J. C. M., Štacko, P., Roke, D., Wolters, A. T., Heideman, H., Chang, M.-C., Van der Meulen, P., Visser, J., Otten, E. & Feringa, B. L., 19 Jul 2017, In: Journal of the American Chemical Society. 139, 28, p. 9650 - 9661 12 p.
Research output: Contribution to journal › Article › Academic › peer-review

Open Access
From chaos to order: Chain-length dependence of the free energy of formation of meso-tetraalkylporphyrin self-assembled monolayer polymorphs
Reimers, J. R., Panduwinata, D., Visser, J., Chin, Y., Tang, C., Goerigk, L., Ford, M. J., Baker, M., Sum, T.-J., Coenen, M. J. J., Hendriksen, B. L. M., Elemans, J. A. A. W., Hush, N. S. & Crossley, M. J., 5 Jan 2016, In: Journal of Physical Chemistry C. 120, 3, p. 1739 - 1748 10 p.
Research output: Contribution to journal › Article › Academic › peer-review

Open Access
A priori calculations of the free energy of formation from solution of polymorphic self-Assembled monolayers
Reimers, J. R., Panduwinata, D., Visser, J., Tang, C., Goerigk, L., Ford, M. J., Sintic, M., Sum, T.-J., Coenen, M. J. J., Hendriksen, B. L. M., Elemans, J. A. A. W., Hush, N. S. & Crossley, M. J., 28 Oct 2015, In: Proceedings of the National Academy of Sciences. 112, 45, p. E6101 - E6110 10 p.
Research output: Contribution to journal › Article › Academic › peer-review

Open Access

1 Oral presentation

Electrosynthesis of furans from grass
Visser, J. (Speaker)
9 Oct 2018
Activity: Talk or presentation › Oral presentation

Cite this

@article{2b38fcc7dd4a4da1908c56430db92415,

title = "Self-organized monolayer of meso-tetradodecylporphyrin coordinated to Au(111)",

abstract = "The structure of molecular monolayers formed at the interface between atomically flat surfaces and a solution of free-base meso-tetradodecylporphyrins (H2Ps) was examined by scanning tunneling microscopy (STM) at the liquid/solid interface. On the surface of graphite (HOPG), H2Ps form a well-ordered monolayer characterized by an oblique unit cell. On Au(111), H2Ps form a self-organized monolayer comprised of two distinct domain types. In both types of domains, the density of the porphyrin cores is increased in comparison to the arrangement observed on HOPG. Also, high-resolution STM images reveal that, in contrast to what is observed on HOPG, physisorption on Au(111) induces a distortion of the porphyrin macrocycle out of planarity. By using X-ray photoelectron spectroscopy, we demonstrate that this is likely to be due to the coordination of the lone pairs of the iminic (−CN−) nitrogen atoms of the porphyrin macrocycle to Au(111).",

keywords = "molecular monolayers, structure, meso-tetradodecylporphyrins, scanning tunneling microscopy, moleculaire monolaag, structuur, meso-tetradodecylporfyrinen, scanning tunneling microscopie",

author = "Nathalie Katsonis and Javier Vicario and Tibor Kudernac and Johan Visser and Pollard, \{Michael M.\} and Ben Feringa",

year = "2006",

month = nov,

day = "1",

doi = "10.1021/ja065823o",

language = "English",

volume = "128",

pages = "15537 -- 15541",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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T1 - Self-organized monolayer of meso-tetradodecylporphyrin coordinated to Au(111)

AU - Katsonis, Nathalie

AU - Vicario, Javier

AU - Kudernac, Tibor

AU - Visser, Johan

AU - Pollard, Michael M.

AU - Feringa, Ben

PY - 2006/11/1

Y1 - 2006/11/1

N2 - The structure of molecular monolayers formed at the interface between atomically flat surfaces and a solution of free-base meso-tetradodecylporphyrins (H2Ps) was examined by scanning tunneling microscopy (STM) at the liquid/solid interface. On the surface of graphite (HOPG), H2Ps form a well-ordered monolayer characterized by an oblique unit cell. On Au(111), H2Ps form a self-organized monolayer comprised of two distinct domain types. In both types of domains, the density of the porphyrin cores is increased in comparison to the arrangement observed on HOPG. Also, high-resolution STM images reveal that, in contrast to what is observed on HOPG, physisorption on Au(111) induces a distortion of the porphyrin macrocycle out of planarity. By using X-ray photoelectron spectroscopy, we demonstrate that this is likely to be due to the coordination of the lone pairs of the iminic (−CN−) nitrogen atoms of the porphyrin macrocycle to Au(111).

AB - The structure of molecular monolayers formed at the interface between atomically flat surfaces and a solution of free-base meso-tetradodecylporphyrins (H2Ps) was examined by scanning tunneling microscopy (STM) at the liquid/solid interface. On the surface of graphite (HOPG), H2Ps form a well-ordered monolayer characterized by an oblique unit cell. On Au(111), H2Ps form a self-organized monolayer comprised of two distinct domain types. In both types of domains, the density of the porphyrin cores is increased in comparison to the arrangement observed on HOPG. Also, high-resolution STM images reveal that, in contrast to what is observed on HOPG, physisorption on Au(111) induces a distortion of the porphyrin macrocycle out of planarity. By using X-ray photoelectron spectroscopy, we demonstrate that this is likely to be due to the coordination of the lone pairs of the iminic (−CN−) nitrogen atoms of the porphyrin macrocycle to Au(111).

KW - molecular monolayers

KW - structure

KW - meso-tetradodecylporphyrins

KW - scanning tunneling microscopy

KW - moleculaire monolaag

KW - structuur

KW - meso-tetradodecylporfyrinen

KW - scanning tunneling microscopie

U2 - 10.1021/ja065823o

DO - 10.1021/ja065823o

M3 - Article

SN - 0002-7863

VL - 128

SP - 15537

EP - 15541

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 48

ER -

Self-organized monolayer of meso-tetradodecylporphyrin coordinated to Au(111)

Abstract

Keywords

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Research output

Third-Generation Light-Driven Symmetric Molecular Motors

From chaos to order: Chain-length dependence of the free energy of formation of meso-tetraalkylporphyrin self-assembled monolayer polymorphs

A priori calculations of the free energy of formation from solution of polymorphic self-Assembled monolayers

Activities

Electrosynthesis of furans from grass

Cite this