Publication

Modification of Supramolecular Binding Motifs Induced By Substrate Registry: Formation of Self-Assembled Macrocycles and Chain-Like Patterns

Fendt, L-A., Stöhr, M., Wintjes, N., Enache, M., Jung, T. A. & Diederich, F., 2009, In : Chemistry. 15, 42, p. 11139-11150 12 p.

Research output: Contribution to journalArticleAcademicpeer-review

APA

Fendt, L-A., Stöhr, M., Wintjes, N., Enache, M., Jung, T. A., & Diederich, F. (2009). Modification of Supramolecular Binding Motifs Induced By Substrate Registry: Formation of Self-Assembled Macrocycles and Chain-Like Patterns. Chemistry, 15(42), 11139-11150. https://doi.org/10.1002/chem.200901502

Author

Fendt, Leslie-Anne ; Stöhr, Meike ; Wintjes, Nikolai ; Enache, Mihaela ; Jung, Thomas A. ; Diederich, François. / Modification of Supramolecular Binding Motifs Induced By Substrate Registry : Formation of Self-Assembled Macrocycles and Chain-Like Patterns. In: Chemistry. 2009 ; Vol. 15, No. 42. pp. 11139-11150.

Harvard

Fendt, L-A, Stöhr, M, Wintjes, N, Enache, M, Jung, TA & Diederich, F 2009, 'Modification of Supramolecular Binding Motifs Induced By Substrate Registry: Formation of Self-Assembled Macrocycles and Chain-Like Patterns', Chemistry, vol. 15, no. 42, pp. 11139-11150. https://doi.org/10.1002/chem.200901502

Standard

Modification of Supramolecular Binding Motifs Induced By Substrate Registry : Formation of Self-Assembled Macrocycles and Chain-Like Patterns. / Fendt, Leslie-Anne; Stöhr, Meike; Wintjes, Nikolai; Enache, Mihaela; Jung, Thomas A.; Diederich, François.

In: Chemistry, Vol. 15, No. 42, 2009, p. 11139-11150.

Research output: Contribution to journalArticleAcademicpeer-review

Vancouver

Fendt L-A, Stöhr M, Wintjes N, Enache M, Jung TA, Diederich F. Modification of Supramolecular Binding Motifs Induced By Substrate Registry: Formation of Self-Assembled Macrocycles and Chain-Like Patterns. Chemistry. 2009;15(42):11139-11150. https://doi.org/10.1002/chem.200901502


BibTeX

@article{e0cc3309db9d4cdd8282646bd813a8bf,
title = "Modification of Supramolecular Binding Motifs Induced By Substrate Registry: Formation of Self-Assembled Macrocycles and Chain-Like Patterns",
abstract = "The self-assembly properties of two Zn(II) porphyrin isomers on Cu(111) are studied at different coverage by means of scanning tunneling microscopy (STM). Both isomers are substituted in their meso-positions by two voluminous 3,5-di(tert-butyl)phenyl and two rod-like 4'-cyanobiphenyl groups, respectively. In the trans-isomer, the two 4'-cyanobiphenyl groups are opposite to each other, whereas they are located at right angle in the cis-isomer. For coverage up to one monolayer, the cis-substituted porphyrins self-assemble to form oligomeric macrocycles held together by antiparallel CN center dot center dot center dot CN dipolar interactions and CN center dot center dot center dot H-C(sp(2)) hydrogen bonding. Cyclic trimers and tetramers occur most frequently but everything from cyclic dimers to hexamers can be observed. Upon annealing of the samples at temperatures >150 degrees C, dimeric macrocyclic structures are observed, in which the two porphyrins are bridged by Cu atoms, originating from the surface, under formation of two CN center dot center dot center dot Cu center dot center dot center dot NC coordination bonds. The trans-isomer builds up linear chains on Cu(111) at low coverage, whereas for higher coverage the molecules assemble in a periodic, densely packed structure. Both cis- and trtins-bis(4'-cyanobiphenyl)-substituted Zn(II) porphyrins behave very differently on Cu(111) compared to similar porphyrins in literature on less reactive surfaces such as Au(111) and Ag(111). On the latter surfaces, there is no signal visible between molecular orientation and the crystal directions of the substrate, whereas on Cu(I 11), very strong adsorbate-substrate interactions have a dominating influence on all observed structures. This strong porphyrin-substrate interaction enables a much broader variety of structures, including also less favorable intermolecular bonding motifs and geometries.",
keywords = "porphyrinoids, scanning probe microscopy, self-assemby, supramolecular chemistry, surfaces, SCANNING-TUNNELING-MICROSCOPY, PORPHYRIN MOLECULES, SURFACES, NANOMATERIALS, CONFORMATION, NETWORKS, DYNAMICS, AG(111)",
author = "Leslie-Anne Fendt and Meike St{\"o}hr and Nikolai Wintjes and Mihaela Enache and Jung, {Thomas A.} and Fran{\cc}ois Diederich",
note = "Relation: https://www.rug.nl/zernike/ Rights: University of Groningen, Zernike Institute for Advanced Materials",
year = "2009",
doi = "10.1002/chem.200901502",
language = "English",
volume = "15",
pages = "11139--11150",
journal = "Chemistry",
issn = "0947-6539",
publisher = "WILEY-V C H VERLAG GMBH",
number = "42",

}

RIS

TY - JOUR

T1 - Modification of Supramolecular Binding Motifs Induced By Substrate Registry

T2 - Formation of Self-Assembled Macrocycles and Chain-Like Patterns

AU - Fendt, Leslie-Anne

AU - Stöhr, Meike

AU - Wintjes, Nikolai

AU - Enache, Mihaela

AU - Jung, Thomas A.

AU - Diederich, François

N1 - Relation: https://www.rug.nl/zernike/ Rights: University of Groningen, Zernike Institute for Advanced Materials

PY - 2009

Y1 - 2009

N2 - The self-assembly properties of two Zn(II) porphyrin isomers on Cu(111) are studied at different coverage by means of scanning tunneling microscopy (STM). Both isomers are substituted in their meso-positions by two voluminous 3,5-di(tert-butyl)phenyl and two rod-like 4'-cyanobiphenyl groups, respectively. In the trans-isomer, the two 4'-cyanobiphenyl groups are opposite to each other, whereas they are located at right angle in the cis-isomer. For coverage up to one monolayer, the cis-substituted porphyrins self-assemble to form oligomeric macrocycles held together by antiparallel CN center dot center dot center dot CN dipolar interactions and CN center dot center dot center dot H-C(sp(2)) hydrogen bonding. Cyclic trimers and tetramers occur most frequently but everything from cyclic dimers to hexamers can be observed. Upon annealing of the samples at temperatures >150 degrees C, dimeric macrocyclic structures are observed, in which the two porphyrins are bridged by Cu atoms, originating from the surface, under formation of two CN center dot center dot center dot Cu center dot center dot center dot NC coordination bonds. The trans-isomer builds up linear chains on Cu(111) at low coverage, whereas for higher coverage the molecules assemble in a periodic, densely packed structure. Both cis- and trtins-bis(4'-cyanobiphenyl)-substituted Zn(II) porphyrins behave very differently on Cu(111) compared to similar porphyrins in literature on less reactive surfaces such as Au(111) and Ag(111). On the latter surfaces, there is no signal visible between molecular orientation and the crystal directions of the substrate, whereas on Cu(I 11), very strong adsorbate-substrate interactions have a dominating influence on all observed structures. This strong porphyrin-substrate interaction enables a much broader variety of structures, including also less favorable intermolecular bonding motifs and geometries.

AB - The self-assembly properties of two Zn(II) porphyrin isomers on Cu(111) are studied at different coverage by means of scanning tunneling microscopy (STM). Both isomers are substituted in their meso-positions by two voluminous 3,5-di(tert-butyl)phenyl and two rod-like 4'-cyanobiphenyl groups, respectively. In the trans-isomer, the two 4'-cyanobiphenyl groups are opposite to each other, whereas they are located at right angle in the cis-isomer. For coverage up to one monolayer, the cis-substituted porphyrins self-assemble to form oligomeric macrocycles held together by antiparallel CN center dot center dot center dot CN dipolar interactions and CN center dot center dot center dot H-C(sp(2)) hydrogen bonding. Cyclic trimers and tetramers occur most frequently but everything from cyclic dimers to hexamers can be observed. Upon annealing of the samples at temperatures >150 degrees C, dimeric macrocyclic structures are observed, in which the two porphyrins are bridged by Cu atoms, originating from the surface, under formation of two CN center dot center dot center dot Cu center dot center dot center dot NC coordination bonds. The trans-isomer builds up linear chains on Cu(111) at low coverage, whereas for higher coverage the molecules assemble in a periodic, densely packed structure. Both cis- and trtins-bis(4'-cyanobiphenyl)-substituted Zn(II) porphyrins behave very differently on Cu(111) compared to similar porphyrins in literature on less reactive surfaces such as Au(111) and Ag(111). On the latter surfaces, there is no signal visible between molecular orientation and the crystal directions of the substrate, whereas on Cu(I 11), very strong adsorbate-substrate interactions have a dominating influence on all observed structures. This strong porphyrin-substrate interaction enables a much broader variety of structures, including also less favorable intermolecular bonding motifs and geometries.

KW - porphyrinoids

KW - scanning probe microscopy

KW - self-assemby

KW - supramolecular chemistry

KW - surfaces

KW - SCANNING-TUNNELING-MICROSCOPY

KW - PORPHYRIN MOLECULES

KW - SURFACES

KW - NANOMATERIALS

KW - CONFORMATION

KW - NETWORKS

KW - DYNAMICS

KW - AG(111)

U2 - 10.1002/chem.200901502

DO - 10.1002/chem.200901502

M3 - Article

VL - 15

SP - 11139

EP - 11150

JO - Chemistry

JF - Chemistry

SN - 0947-6539

IS - 42

ER -

ID: 2677325