Self-Assembled Two-Dimensional Molecular Host-Guest Architectures From Trimesic Acid

Griessl, Stefan; Lackinger, Markus; Edelwirth, Michael; Hietschold, Michael; Heckl, Wolfgang M.

doi:10.1002/1438-5171(200204)3:1<25::aid-simo25>3.3.co;2-b

Cited by 192 publications

(390 citation statements)

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“…The trimer junction in the hexagonal phase is similar to that in the "flower" structure formed by trimesic acid and related molecules. 9,32 In the topographic profile shown in Figure 1 the height of the molecular layers is measured to be 0.26 ( 0.015 nm. This height, and the close agreement between measured and calculated lateral dimensions, provides strong evidence that the molecules are adsorbed with the porphyrin macrocycle approximately parallel to the surface in an arrangement stabilized by hydrogen bonding.…”

Section: Resultsmentioning

confidence: 99%

van der Waals-Induced Chromatic Shifts in Hydrogen-Bonded Two-Dimensional Porphyrin Arrays on Boron Nitride

Korolkov¹,

Svatek²,

Summerfield³

et al. 2015

ACS Nano

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The fluorescence of a two-dimensional supramolecular network of 5,10,15,20-tetrakis(4-carboxylphenyl)porphyrin (TCPP) adsorbed on hexagonal boron nitride (hBN) is red-shifted due to, primarily, adsorbate-substrate van der Waals interactions. TCPP is deposited from solution on hBN and forms faceted islands with typical dimensions of 100 nm and either square or hexagonal symmetry. The molecular arrangement is stabilized by in-plane hydrogen bonding as determined by a combination of molecular-resolution atomic force microscopy performed under ambient conditions and density functional theory; a similar structure is observed on MoS2 and graphite. The fluorescence spectra of submonolayers of TCPP on hBN are red-shifted by ∼30 nm due to the distortion of the molecule arising from van der Waals interactions, in agreement with time-dependent density functional theory calculations. Fluorescence intensity variations are observed due to coherent partial reflections at the hBN interface, implying that such hybrid structures have potential in photonic applications.

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Section: Resultsmentioning

confidence: 99%

van der Waals-Induced Chromatic Shifts in Hydrogen-Bonded Two-Dimensional Porphyrin Arrays on Boron Nitride

Korolkov¹,

Svatek²,

Summerfield³

et al. 2015

ACS Nano

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“…1a,b, TMA forms an extended honeycomb-like structure when adsorbed at the solid–liquid interface between its solution in heptanoic acid and HOPG. The hexagonal cavities of the periodic arrangement are created by the di-apto hydrogen-bonding of adjacent carboxylic acid groups of six neighbouring molecules, exhibiting a pore diameter of about 12 Å (refs 12, 28). Figure 1c shows a scanning tunnelling microscopy (STM)34 height image of the chicken-wire structure of the 2D TMA-crystal on HOPG upon the addition of a small drop of saturated heptanoic acid solution; the unit cell parameters agree with previous reports1231.…”

Section: Resultsmentioning

confidence: 99%

“…Hydrogen-bonding is the most versatile, yet specific type of weak interaction to engineer two-dimensional (2D) self-assembled networks56 due to the high level of control at the molecular level78 and the potential applications9. Among other supramolecular interactions, host–guest complexation on 2D networks provides an interesting platform to create functional multicomponent layers1011, nanostructures1213 and prototypical devices14, and establish the first step to tailor 3D architectures1516. Furthermore, donor (D) - acceptor (A) complexation of common acceptor molecules into the core of giant macrocycles unveils promising building blocks for the fabrication of complex nanostructures15171819 and self-assembled devices.…”

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confidence: 99%

“…This architecture is achieved by combining the spontaneous formation of a hydrogen-bonded trimesic acid (TMA, 1 ) as a 2D-template at the interface between its heptanoic acid solution and a highly oriented pyrolytic graphite (HOPG) substrate1228, the complexation of oligothiophene macrocycles2930 and C 60 in solution, and the site recognition of the cavities in the TMA monolayer by C 60 (ref. 31).…”

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Templated bilayer self-assembly of fully conjugated π-expanded macrocyclic oligothiophenes complexed with fullerenes

2017

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Fully conjugated macrocyclic oligothiophenes exhibit a combination of highly attractive structural, optical and electronic properties, and multifunctional molecular thin film architectures thereof are envisioned. However, control over the self-assembly of such systems becomes increasingly challenging, the more complex the target structures are. Here we show a robust self-assembly based on hierarchical non-covalent interactions. A self-assembled monolayer of hydrogen-bonded trimesic acid at the interface between an organic solution and graphite provides host-sites for the epitaxial ordering of Saturn-like complexes of fullerenes with oligothiophene macrocycles in mono- and bilayers. STM tomography verifies the formation of the templated layers. Molecular dynamics simulations corroborate the conformational stability and assign the adsorption sites of the adlayers. Scanning tunnelling spectroscopy determines their rectification characteristics. Current–voltage characteristics reveal the modification of the rectifying properties of the macrocycles by the formation of donor–acceptor complexes in a densely packed all-self-assembled supramolecular nanostructure.

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“…Hydrogen bonding : A substantial number of systems describing the formation one‐41–46 and two‐component47–50 2D porous networks in which the components are held together by hydrogen‐bonding interactions have been published in the last decade. One of the first examples of two‐component networks featuring empty hexagonal domains able host molecular guests, such as fullerenes, was reported in 2003 by the groups of Beton, Champness and co‐workers 48.…”

Section: Porous Networkmentioning

confidence: 99%

Supramolecular Chemistry at Interfaces: Molecular Recognition on Nanopatterned Porous Surfaces

Bonifazi

Mohnani

Llanes‐Pallas

2009

Chemistry A European J

252

219

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Through the illustration of key examples that have recently appeared in the literature, the intention of this review is to provide a perspective of current advances on the molecular recognition at the interfaces aimed at the engineering of multifunctional organic-based materials. The great interest in such systems has been motivated by the need to fabricate smaller and smaller components in order to improve, for example, the information storage capabilities of classical silicon-based devices. Although great progress has been achieved on the exploitation of "top-down" approaches, strong hope is now put on the development of hybrid devices in which the elementary components are replaced with single organic molecules. Nevertheless, the drive towards such devices is restricted by both their stability and difficulties to precisely control and manipulate the structural organisation at the molecular level. To overcome these restrictions, the use of nanotemplated surfaces featuring porous domains in which responsive functional molecules can be precisely accommodated at the single-molecule level is one of the most promising approaches. In the first part of this manuscript, we therefore illustrate the main engineering strategies [1) through non-covalent interactions, 2) surface-confined covalent reactions and 3) assembly of pre-organised cavities such as synthetic macrocycles] currently in use to create two-dimensional (2D) patterned surfaces displaying porous structures at the nanoscale level. Such networks, featuring periodic hollow domains (controllable both in shape and size), are of particular significance as their cavities can be used as receptors for the recognition of remotely controllable functional molecules. In the second part, the confinement of molecular guests within the cavities is discussed, emphasising the selectivity and dynamics of key assemblies, with a particular focus on the biomolecular recognition and post-assembly covalent functionalisation, which could provide the opportunity to fabricate devices currently beyond our reach on an unprecedented precision and efficiency. All the examples will be discussed in terms of structural organisation as studied by scanning tunnelling microscopy (STM) techniques.

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Self-Assembled Two-Dimensional Molecular Host-Guest Architectures From Trimesic Acid

Cited by 192 publications

References 9 publications

van der Waals-Induced Chromatic Shifts in Hydrogen-Bonded Two-Dimensional Porphyrin Arrays on Boron Nitride

van der Waals-Induced Chromatic Shifts in Hydrogen-Bonded Two-Dimensional Porphyrin Arrays on Boron Nitride

Templated bilayer self-assembly of fully conjugated π-expanded macrocyclic oligothiophenes complexed with fullerenes

Supramolecular Chemistry at Interfaces: Molecular Recognition on Nanopatterned Porous Surfaces

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