Supramolecular Ordering in Oligothiophene−Fullerene Monolayers

MacLeod, Jennifer; Ivasenko, Oleksandr; Fu, Chaoying; Taerum, Tyler; Rosei, Federico; Perepichka, Dmitrii F.

doi:10.1021/ja906206g

Cited by 136 publications

(152 citation statements)

References 76 publications

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“…This value is lower than both our previously calculated value of −10.01 kcal/mol per −COOH (B3LYP/6-31G(d,p)) 52 and a published value that made use of the LDA (−10.26 kcal/mol per −COOH). 51 However, this discrepancy seems to be largely due to the use of vdW-DF in our calculations; PBE-GGA without vdW-DF gives a R 2 2 (8) bond energy of −9.60 kcal/mol per −COOH.…”

Section: Resultscontrasting

confidence: 79%

Substrate Effects in the Supramolecular Assembly of 1,3,5-Benzene Tricarboxylic Acid on Graphite and Graphene

et al. 2015

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The behavior of small molecules on a surface depends critically on both molecule−substrate and intermolecular interactions. We present here a detailed comparative investigation of 1,3,5-benzene tricarboxylic acid (trimesic acid, TMA) on two different surfaces: highly oriented pyrolytic graphite (HOPG) and single-layer graphene (SLG) grown on a polycrystalline Cu foil. On the basis of high-resolution scanning tunnelling microscopy (STM) images, we show that the epitaxy matrix for the hexagonal TMA chicken wire phase is identical on these two surfaces, and, using density functional theory (DFT) with a non-local van der Waals correlation contribution, we identify the most energetically favorable adsorption geometries. Simulated STM images based on these calculations suggest that the TMA lattice can stably adsorb on sites other than those identified to maximize binding interactions with the substrate. This is consistent with our net energy calculations that suggest that intermolecular interactions (TMA−TMA dimer bonding) are dominant over TMA−substrate interactions in stabilizing the system. STM images demonstrate the robustness of the TMA films on SLG, where the molecular network extends across the variable topography of the SLG substrates and remains intact after rinsing and drying the films. These results help to elucidate molecular behavior on SLG and suggest significant similarities between adsorption on HOPG and SLG.

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Section: Resultscontrasting

confidence: 79%

Substrate Effects in the Supramolecular Assembly of 1,3,5-Benzene Tricarboxylic Acid on Graphite and Graphene

et al. 2015

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“…With this method, the self-assembly of oligo- and polythiophenes on surfaces has been successfully investigated in the last few years [5–6 9–14]. The 2-D crystalline arrangement on surfaces is a result of a delicate balance between several weak intermolecular van der Waals forces and molecule–substrate interactions, as well as intermolecular hydrogen bonding in the case of functionalized oligothiophenes [15–17]. The typical flat metallic substrates (HOPG, Au(111), Ag(111), etc.)…”

Section: Introductionmentioning

confidence: 99%

STM study on the self-assembly of oligothiophene-based organic semiconductors

Mena‐Osteritz¹,

Urdanpilleta²,

El-Hosseiny³

et al. 2011

Beilstein J. Nanotechnol.

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SummaryThe self-assembly properties of a series of functionalized regioregular oligo(3-alkylthiophenes) were investigated by using scanning tunneling microscopy (STM) at the liquid–solid interface under ambient conditions. The characteristics of the 2-D crystals formed on the (0001) plane of highly ordered pyrolitic graphite (HOPG) strongly depend on the length of the π-conjugated oligomer backbone, on the functional groups attached to it, and on the alkyl substitution pattern on the individual thiophene units. Theoretical calculations were performed to analyze the geometry and electronic density of the molecular orbitals as well as to analyze the intermolecular interactions, in order to obtain models of the 2-D molecular ordering on the substrate.

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“…The PCDA molecule contains typical structural and functional features such as alkyl chains and a carboxylic acid headgroup that are known to foster supramolecular self-assembly at the liquid–solid interface on graphite. 34−37 …”

mentioning

confidence: 99%

Self-Assembly under Confinement: Nanocorrals for Understanding Fundamentals of 2D Crystallization

et al. 2016

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Nanocorrals with different size, shape, and orientation are created on covalently modified highly oriented pyrolytic graphite surfaces using scanning probe nanolithography, i.e., nanoshaving. Alkylated diacetylene molecules undergo laterally confined supramolecular self-assembly within these corrals. When nanoshaving is performed in situ, at the liquid–solid interface, the orientation of the supramolecular lamellae structure is directionally influenced by the gradual graphite surface exposure. Careful choice of the nanoshaving direction with respect to the substrate symmetry axes promotes alignment of the supramolecular lamellae within the corral. Self-assembly occurring inside corrals of different size and shape reveals the importance of geometric and kinetic constraints controlled by the nanoshaving process. Finally, seed-mediated crystallization studies demonstrate confinement control over nucleation and growth principles.

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Supramolecular Ordering in Oligothiophene−Fullerene Monolayers

Cited by 136 publications

References 76 publications

Substrate Effects in the Supramolecular Assembly of 1,3,5-Benzene Tricarboxylic Acid on Graphite and Graphene

Substrate Effects in the Supramolecular Assembly of 1,3,5-Benzene Tricarboxylic Acid on Graphite and Graphene

STM study on the self-assembly of oligothiophene-based organic semiconductors

Self-Assembly under Confinement: Nanocorrals for Understanding Fundamentals of 2D Crystallization

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