Tailoring Surface‐Confined Nanopores with Photoresponsive Groups

Tahara, Kazukuni; Inukai, Koji; Adisoejoso, Jinne; Yamaga, Hiroyuki; Balandina, Tatyana; Blunt, Matthew O.; Feyter, Steven De; Tobe, Yoshito

doi:10.1002/ange.201303745

Cited by 16 publications

(12 citation statements)

References 35 publications

(7 reference statements)

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“…Here a meta-phenylene linker connected to a C12 alkyl chain was used to locate the cyclic hexamer of the dicarboxyazobenzene units at an appropriate direction in the pore (Figure 36). 76 We expected that the azobenzene units initially located on the surface in its planar trans-configuration would be desorbed from the surface after isomerization to the cis-configuration, thereby changing the pore size and shape significantly which can be assessed by the number of adsorbed COR guest molecules.…”

Section: ¹1mentioning

confidence: 99%

Adaptive Building Blocks Consisting of Rigid Triangular Core and Flexible Alkoxy Chains for Self-Assembly at Liquid/Solid Interfaces

Tobe¹,

Tahara²,

Feyter³

2016

Bulletin of the Chemical Society of Japan

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has been a full professor since 2011 at KU Leuven-University of Leuven in Belgium. After starting up scanning tunneling microscopy during his Ph.D. in the group of Prof. Frans C. De Schryver at KU Leuven he moved for a postdoctoral position to the group of Prof. Ahmed Zewail (Caltech) where he was involved in ultrafast organic femtochemistry. His current interests include the study of supramolecular chemistry and self-assembly phenomena at surfaces, including modification of 2D materials, with a focus on liquid-solid interfaces. In 2013, he was awarded an ERC advanced grant. AbstractSupramolecular self-assembly in two-dimensional (2D) spaces on solid surfaces is the subject of intense current interest because of perspectives for various applications in nanoscience and nanotechnology. At the liquid/graphite interface, we found by means of scanning tunneling microscopy molecules with a rigid triangular core, a twelve-membered annulene (DBA), substituted by six flexible alkoxy chains selfassembled to form hexagonal porous 2D molecular networks via van der Waals interactions between interdigitated alkyl chains as the directional intermolecular linkages. Factors that affect the formation of the porous 2D molecular networks including alkyl chain length, solvent, solute concentration, and temperature were elucidated through a systematic study. Because DBA molecules are versatile for chemical modification, they turned out to be highly adaptive for on-surface supramolecular chemistry with respect to (i) pore size control by changing the chain length, (ii) study of parity effect due to even or odd number chains, (iii) generation of supramolecular chirality on surfaces by introducing stereocenters, (iv) chemical modification of the pore interior for selective co-adsorption of guest molecules by introducing functional groups. Additionally, formation of superlattice structures on surfaces was incidentally observed by mixing DBAs of different alkoxy chain parity or by addition of guest molecules via an induced-fit mechanism. These results made significant contribution to advancement of supramolecular chemistry in 2D space.

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Section: ¹1mentioning

confidence: 99%

Adaptive Building Blocks Consisting of Rigid Triangular Core and Flexible Alkoxy Chains for Self-Assembly at Liquid/Solid Interfaces

Tobe¹,

Tahara²,

Feyter³

2016

Bulletin of the Chemical Society of Japan

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“…Therefore, host-guest interactions can easily be studied. Currently, these systems only show selective interactions towards guest adsorption based on size and/or shape complementarity, [10][11][12][13][14][15][16] and chemical environment. 17 Here we show a certain control in the occupation of the 2D porous network based on the chiral complementarity between the guest and the host.…”

mentioning

confidence: 99%

“…The selfassembly of this system at the liquid/solid interfaces has been investigated extensively. [14][15][16][17][18][19][20][21] These alkylated molecules may selfassemble into a nanoporous network at the interface between a liquid and highly oriented pyrolytic graphite (HOPG). Under appropriate solute concentration conditions, highly ordered networks are formed, leaving a regular pattern of hexagonal nanowells.…”

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confidence: 99%

Towards enantioselective adsorption in surface-confined nanoporous systems

et al. 2015

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“…The reorganization induced by an external stimulus can lead to dramatic changes in the adsorbed monolayer. the photodecomposition of diazoanthrone [84] or the photoisomerization of thioindigo [85], anthracene dimer [86], azobenzene [87][88][89][90][91][92][93][94][95], stilbene [94,96], diarylethene [97][98][99][100][101][102][103][104], or terthiophene [105] ( Fig. 4).…”

Section: Supramolecular Control Of Molecular Assemblies Formed At Thementioning

confidence: 99%

“…Design of photoresponsive molecular assembliesBecause the liquid/solid interface is an ideal platform to study 2D supramolecular chemistry, the photoresponsive behavior of molecular assemblies composed of photochromic compounds at the liquid/solid interface has recently attracted interest. Although strong quenching of photoreactions is usually observed on metal surfaces[83], some photoreactions have been reported to occur on HOPG[95].Upon irradiation, photochemical reactions can change the concentration of the solute in the solution and induce changes in the assembly formed at the liquid/solid interface. The ordering transformation occurs by the exchange of molecules between the interface and the solution; thus, understanding of the process of 2D self-assembly is important to control the photoinduced ordering transformation(Fig.…”

mentioning

confidence: 99%

Photoresponsive supramolecular self-assemblies at the liquid/solid interface

Frath

Yokoyama

Hirose

et al. 2018

Journal of Photochemistry and Photobiology C: Photochemistry Re

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Control over molecular nanostructure is of the utmost importance in bottom-up strategies to create functionalized surfaces for electronic devices and advanced materials. In this context, the study of two-dimensional self-assembled structures consisting of organic molecules on surfaces using scanning tunneling microscopy (STM) has been the subject of intensive research. The formation of stimuli-responsive assemblies, especially photoresponsive ones, on surfaces is attracting interest. Meanwhile, assemblies formed at the liquid/solid interface have been extensively studied using STM from a supramolecular chemistry perspective in order to understand the assembly process of the molecules from the solution phase to the substrate interface. In this review, an overview of advances in photoresponsive supramolecular self-assemblies formed at the liquid/solid interface is given. Recent progress in the analysis of the adsorption process using the nucleation-elongation model of two-dimensional self-assembly will be featured and discussed in the context of photochemical control of the assembly.

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Tailoring Surface‐Confined Nanopores with Photoresponsive Groups

Cited by 16 publications

References 35 publications

Adaptive Building Blocks Consisting of Rigid Triangular Core and Flexible Alkoxy Chains for Self-Assembly at Liquid/Solid Interfaces

Adaptive Building Blocks Consisting of Rigid Triangular Core and Flexible Alkoxy Chains for Self-Assembly at Liquid/Solid Interfaces

Towards enantioselective adsorption in surface-confined nanoporous systems

Photoresponsive supramolecular self-assemblies at the liquid/solid interface

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