Janus‐Like 3D Tectons: Self‐Assembled 2D Arrays of Functional Units at a Defined Distance from the Substrate

Bléger, David; Mathevet, Fabrice; Kréher, David; Attias, André Jean; Bocheux, Amandine; Latil, Sylvain; Douillard, Ludovic; Fiorini–Debuisschert, Céline; Charra, Fabrice

doi:10.1002/ange.201008212

Cited by 5 publications

(4 citation statements)

References 41 publications

(2 reference statements)

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“…The estimated unit cell dimensions are a =2.08 nm, b =3.84 nm, and α =64°. These values are in accordance, within experimental errors, with those obtained previously for the basal plane . Thus, the self‐organization ability of the basal plane is not impaired by the bulky C 60 substituent.…”

Section: Methodssupporting

confidence: 91%

“…Therefore, it is of great interest to provide fullerene 3D building‐blocks covalently incorporating a C60 unit and designed to ensure surface‐confined supramolecular self‐assembly, on the one hand, and expose functionalized C 60 units organized in well‐ordered arrays above the substrate, on the other hand. Recently, we introduced the Janus molecular tecton concept as a tool for surface‐confined supramolecular self‐assembly . This new kind of 3D Janus material can simultaneously form well‐ordered adlayers on sp 2 ‐hybridized‐carbon‐based substrates and expose a desired functionality over a surface.…”

Section: Methodsmentioning

confidence: 99%

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Surface‐Confined Supramolecular Self‐Assembly of Molecular Nanocranes for Chemically Lifting and Positioning C₆₀ above a Conducting Substrate

Kréher

Mathevet

et al. 2015

ChemPhysChem

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2D supramolecular self-assembly is a good way to form well-defined nanostructures on various substrates. One of the current challenges is to extend this approach to 3D functional building blocks. Here, we address this issue by providing a strategy for the controlled lifting and positioning of functional units above a graphitic substrate. This is the first time that multistory cyclophane-based 3D tectons incorporating C60 units have been designed and synthesized. Molecular modelling provides a description of the 3D geometries and evidences the flexible character of the building blocks. Despite this later feature, the supramolecular self-assembly of Janus tectons on HOPG yields well-ordered adlayers incorporating C60 arrays at well-defined mean distances from the surface. As our approach is not limited to C60 , the results reported here open-up possibilities for applications where the topological and electronic interactions between the substrate and the functional unit are of prime importance.

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Section: Methodssupporting

confidence: 91%

Section: Methodsmentioning

confidence: 99%

Surface‐Confined Supramolecular Self‐Assembly of Molecular Nanocranes for Chemically Lifting and Positioning C₆₀ above a Conducting Substrate

Kréher

Mathevet

et al. 2015

ChemPhysChem

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“…In the second stage, the design of 3D building blocks was pursued [29]. This strategy is motivated by the need for functional surfaces for demanding forthcoming applications in nanotechnology.…”

Section: D Tectons For the Controlled Placement Of Functional Molecumentioning

confidence: 99%

“…3D Janus tecton: schematic structure of the two-faced building block laying on the substrate (alkyl chains are omitted for clarity), and large-scale STM image (49.3 x 49.3 nm 2 ) of the selfassembly at the HOPG-phenyloctane interface. The scaled model of the molecular assembly is superimposed on the STM picture (only lower levels A are represented for clarity).Figure adaptedwith permission from[29], copyright 2011 Wiley-VCH Verlag GmbH & Co.…”

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confidence: 99%

A versatile strategy towards non-covalent functionalization of graphene by surface-confined supramolecular self-assembly of Janus tectons

Du¹,

Bléger²,

Charra³

et al. 2016

Nano Online

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Surface‐Confined Self‐Assembled Janus Tectons: A Versatile Platform towards the Noncovalent Functionalization of Graphene

Jaouen

Bocheux

et al. 2014

Angewandte Chemie

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A general strategy for simultaneously generating surface-based supramolecular architectures on flat sp 2 -hybridized carbon supports and independently exposing on demand off-plane functionality with controlled lateral order is highly desirable for the noncovalent functionalization of graphene. Here, we address this issue by providing a versatile molecular platform based on a library of new 3D Janus tectons that form surface-confined supramolecular adlayers in which it is possible to simultaneously steer the 2D self-assembly on flat C(sp 2 )-based substrates and tailor the external interface above the substrate by exposure to a wide variety of small terminal chemical groups and functional moieties. This approach is validated throughout by scanning tunneling microscopy (STM) at the liquid-solid interface and molecular mechanics modeling studies. The successful self-assembly on graphene, together with the possibility to transfer the graphene monolayer onto various substrates, should considerably extend the application of our functionalization strategy.Although adsorbing organic molecules on surfaces is the most used method to modify the properties of the substrate, a strategy for developing complex, well-ordered adlayers with tailored functionalities remains a key issue in nanotechnology. This is why, in addition to covalent functionalization through a strategy based on self-assembled monolayers (SAMs), [1] two-dimensional (2D) supramolecular self-assembly by noncovalent adsorption of planar organic building blocks (tectons) at metal or highly oriented pyrolitic graphite (HOPG) surfaces has attracted considerable interest. [2][3][4][5][6] This approach allows hydrogen bonding, metal-ligand coordination, or alkyl chain interdigitation to be used to generate functional hybrid interfaces of networks that exhibit in-plane functionalities, for example, hosting subsequent deposited species in the case of porous molecular networks. [4,7, 8] Recently, a few elegant strategies exploiting the 2D in-plane positioning on various conducting substrates have been developed to achieve the controlled positioning of molecules out-of the plane so as to add a functionality which does not disturb the 2D selfassembly and which is preserved from possibly detrimental influences of the substrate. These routes towards threedimensional (3D) self-assembled systems consist of the surface-confined self-assembly of 3D tectons, [9] mainly based on cyclophanes, [10] sandwich-type multidecker complexes, [11]

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Janus‐Like 3D Tectons: Self‐Assembled 2D Arrays of Functional Units at a Defined Distance from the Substrate

Cited by 5 publications

References 41 publications

Surface‐Confined Supramolecular Self‐Assembly of Molecular Nanocranes for Chemically Lifting and Positioning C₆₀ above a Conducting Substrate

Surface‐Confined Supramolecular Self‐Assembly of Molecular Nanocranes for Chemically Lifting and Positioning C₆₀ above a Conducting Substrate

A versatile strategy towards non-covalent functionalization of graphene by surface-confined supramolecular self-assembly of Janus tectons

Surface‐Confined Self‐Assembled Janus Tectons: A Versatile Platform towards the Noncovalent Functionalization of Graphene

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Janus‐Like 3D Tectons: Self‐Assembled 2D Arrays of Functional Units at a Defined Distance from the Substrate

Cited by 5 publications

References 41 publications

Surface‐Confined Supramolecular Self‐Assembly of Molecular Nanocranes for Chemically Lifting and Positioning C60 above a Conducting Substrate

Surface‐Confined Supramolecular Self‐Assembly of Molecular Nanocranes for Chemically Lifting and Positioning C60 above a Conducting Substrate

A versatile strategy towards non-covalent functionalization of graphene by surface-confined supramolecular self-assembly of Janus tectons

Surface‐Confined Self‐Assembled Janus Tectons: A Versatile Platform towards the Noncovalent Functionalization of Graphene

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Surface‐Confined Supramolecular Self‐Assembly of Molecular Nanocranes for Chemically Lifting and Positioning C₆₀ above a Conducting Substrate

Surface‐Confined Supramolecular Self‐Assembly of Molecular Nanocranes for Chemically Lifting and Positioning C₆₀ above a Conducting Substrate