Self-Patterned Molecular Photoswitching in Nanoscale Surface Assemblies

Levy, Niv; Comstock, Matthew; Cho, Jongweon; Berbil-Bautista, L.; Kirakosian, A.; Lauterwasser, Frank; Poulsen, Daniel A.; Fréchet, Jean M. J.; Crommie, Michael F.

doi:10.1021/nl802632g

Cited by 31 publications

(32 citation statements)

References 24 publications

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“…It can only be explained in terms of commensurability between the molecular layer and the underlying substrate. A similar effect has been observed for the TBA adsorbed on Au (111) [47].…”

Section: Adsorbate/adsorbate-interactionsupporting

confidence: 82%

Optically and thermally induced molecular switching processes at metal surfaces

Tegeder

2012

J. Phys.: Condens. Matter

123

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Using light to control the switching of functional properties of surface-bound species is an attractive strategy for the development of new technologies with possible applications in molecular electronics and functional surfaces and interfaces. Molecular switches are promising systems for such a route, since they possess the ability to undergo reversible changes between different molecular states and accordingly molecular properties by excitation with light or other external stimuli. In this review, recent experiments on photo- and thermally induced molecular switching processes at noble metal surfaces utilizing two-photon photoemission and surface vibrational spectroscopies are reported. The investigated molecular switches can either undergo a trans-cis isomerization or a ring opening-closure reaction. Two approaches concerning the connection of the switches to the surface are applied: physisorbed switches, i.e. molecules in direct contact with the substrate, and surface-decoupled switches incorporated in self-assembled monolayers. Elementary processes in molecular switches at surfaces, such as excitation mechanisms in photoisomerization and kinetic parameters for thermally driven reactions, which are essential for a microscopic understanding of molecular switching at surfaces, are presented. This in turn is needed for designing an appropriate adsorbate-substrate system with the desired switchable functionality controlled by external stimuli.

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“…It can only be explained in terms of commensurability between the molecular layer and the underlying substrate. A similar effect has been observed for the TBA adsorbed on Au (111) [47].…”

Section: Adsorbate/adsorbate-interactionsupporting

confidence: 82%

Optically and thermally induced molecular switching processes at metal surfaces

Tegeder

2012

J. Phys.: Condens. Matter

123

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“…Photoisomerization of a molecular switch in direct contact with a metal surface has so far been demonstrated for a specifically designed azobenzene derivative, namely the 3,3 0 ,5,5 0 -tetra-tert-butyl-azobenzene (TBA) adsorbed on Au(111). [16][17][18] For TBA it is believed that the bulky tert-butylgroups lead to a decoupling of the functional azobenzene backbone from the metallic substrate. This allows for the photoinduced trans to cis conformational change and the thermally activated back reaction.…”

Section: Introductionmentioning

confidence: 99%

On the electronic and geometrical structure of the trans- and cis-isomer of tetra-tert-butyl-azobenzene on Au(111)

Schmidt

Hagen

Brete

et al. 2010

Phys. Chem. Chem. Phys.

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Near edge X-ray absorption fine structure and X-ray photoelectron spectroscopy have been employed to follow the reversible trans to cis isomerization of tetra-tert-butyl-azobenzene (TBA) adsorbed on Au(111). For one monolayer the molecules adopt an adsorption geometry characteristic of the trans-TBA isomer. The azo-bridge (N = N) is aligned nearly parallel to the surface and the phenyl rings exhibit a planar orientation with a small tilt angle

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“…[2][3] With a few exceptions, [4][5][6][7] most of these studies have focused on azobenzene derivatives on metal surfaces, where isomerization can be induced by light, [8][9] thermal energy, 9 and the tunneling current [10][11] or the electric field 12 from an STM tip. However, it has been shown that different substrates, 13 different surface orientations, 13 or even different areas of the same surface [14][15] can suppress the isomerization for the same molecules. In a recent report the surface has been suggested to lower the energy barrier for isomerization, but no specific mechanism could be identified.…”

mentioning

confidence: 99%

Charge-Transfer-Induced Isomerization of DCNQI on Cu(100)

et al. 2014

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This article reports on the temperature-controlled irreversible transition between the two isomeric forms of the strong electron acceptor dicyano-p-quinonediimine (DCNQI) on the Cu(100) surface. A combination of experiment (time-resolved, variable-temperature scanning tunneling microscopy, STM) and theory (density functional theory, DFT) shows that the isomerization barrier is lower than in the gas phase or solution due to the fact that charge transfer from the substrate modifies the bond configuration of the molecule, aromatizing the quinoid ring of DCNQI and enabling a more free rotation of the cyano groups with respect to the molecular axis.

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Self-Patterned Molecular Photoswitching in Nanoscale Surface Assemblies

Cited by 31 publications

References 24 publications

Optically and thermally induced molecular switching processes at metal surfaces

Optically and thermally induced molecular switching processes at metal surfaces

On the electronic and geometrical structure of the trans- and cis-isomer of tetra-tert-butyl-azobenzene on Au(111)

Charge-Transfer-Induced Isomerization of DCNQI on Cu(100)

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