Solvent Induced Polymorphism in Supramolecular 1,3,5-Benzenetribenzoic Acid Monolayers

Kampschulte, Lorenz; Lackinger, Markus; Maier, Anne-Kathrin; Kishore, Ravuri S. K.; Griessl, Stefan; Schmittel, Michael; Heckl, Wolfgang M.

doi:10.1021/jp057553m

Cited by 213 publications

(280 citation statements)

References 42 publications

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“…6A,B). Differently from what was shown for C 60 , it was not possible to transfer a molecule from one site to another since most of the sites were occupied.…”

Section: Tma and Other Benzoic Acidsmentioning

confidence: 60%

“…Porous networks similar to those obtained from TMA were also built from 1,3,5-benzenetribenzoic acid (BTB) [60]. Also these studies were carried out on graphite substrates at the solid/liquid interface.…”

Section: Tma and Other Benzoic Acidsmentioning

confidence: 99%

“…Reprinted with permission from [60]. © (2006) American Chemical Society to lie close to the rim of the cavities, so as to maximize π-π interactions.…”

Section: Tma and Other Benzoic Acidsmentioning

confidence: 99%

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Two-Dimensional Nanotemplates as Surface Cues for the Controlled Assembly of Organic Molecules

Cicoira

Santato

Rosei

2008

Topics in Current Chemistry

108

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“…6A,B). Differently from what was shown for C 60 , it was not possible to transfer a molecule from one site to another since most of the sites were occupied.…”

Section: Tma and Other Benzoic Acidsmentioning

confidence: 60%

Section: Tma and Other Benzoic Acidsmentioning

confidence: 99%

See 1 more Smart Citation

Two-Dimensional Nanotemplates as Surface Cues for the Controlled Assembly of Organic Molecules

Cicoira

Santato

Rosei

2008

Topics in Current Chemistry

108

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“…22 This was attributed to minimization of electrostatic effect, i.e. more hydrophobic is the solvent, less polar and less dense are the generated self-assembled organic structures.…”

Section: Resultsmentioning

confidence: 99%

Two-Dimensional 1,3,5-Tris(4-carboxyphenyl)benzene Self-Assembly at the 1-Phenyloctane/Graphite Interface Revisited

Silly

2012

J. Phys. Chem. C

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This document is the unedited author's version of a Submitted Work that was subsequently accepted for publication in Journal of Physical Chemistry C, copyright c American Chemical Society after peer review. To access the final edited and published work see http://pubs.rsc.org/en/journals/journalissues/tc. Two-dimensional (2D) self-assembly of star-shaped 1,3,5-Tris(4-carboxyphenyl)benzene molecules is investigated. Scanning tunneling microscopy reveals that this molecule can form three hydrogen-bonded networks at the 1-phenyloctane/graphite interface. One of these structures is close-packed and the two other ones are porous structures, with hexagonal and rectangular cavities. The network with rectangular cavities appears to be the most stable structure.2

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“…However, empirical heuristics describing the interplay of physisorption, molecule-molecule interaction, solvent and concentration effects are emerging from carefully-controlled experiments. [17][18][19][20] Until recently, temperature was the only variable in the Gibbs free energy expression that had not been systematically varied, even though it has implications for both thermodynamics and kinetics, as well as for critical parameters like solubility and viscosity. We highlight here the first few reports of temperature control in SSI-STM experiments.…”

mentioning

confidence: 99%

Expanding the Scope of Molecular Self-organization Studies through Temperature Control at the Solution/Solid Interface

MacLeod

Rosei

2011

Aust. J. Chem.

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Studying the self-assembly of molecules at the solution/solid interface (SSI) provides unique insight into bottom-up molecular architectures, which have applications varying from solar conversion [1][2][3] and electronic devices [4][5][6][7] to providing insight into fundamental biological mechanisms. [8,9] The investigation of molecular organization at the SSI is largely conducted via scanning tunnelling microscopy (STM), which can be used to directly visualize molecular kinetics and geometries in situ. [10][11][12][13][14] The development of this technique has provided unprecedented access to the details of surface molecular self-assembly. [15,16] The Gibbs free energy for molecular systems at the SSI comprises an enthalpic contribution dominated by the interaction energies of the adsorbed species (intermolecular and molecule-substrate) and an entropic component primarily associated with the molecules in solution. The details of the energy balance are quite subtle, and the level of ab initio predictive power necessary for the ground-up design of molecular networks remains elusive. However, empirical heuristics describing the interplay of physisorption, molecule-molecule interaction, solvent and concentration effects are emerging from carefully-controlled experiments. [17][18][19][20] Until recently, temperature was the only variable in the Gibbs free energy expression that had not been systematically varied, even though it has implications for both thermodynamics and kinetics, as well as for critical parameters like solubility and viscosity. We highlight here the first few reports of temperature control in SSI-STM experiments.The infrastructure required to modify an existing STM for temperature control is modest, and designs can be easily adapted from add-on stages originally intended for commercial atomic force microscopy. [21][22][23] In general, temperatures above room temperature are achieved by inserting either a small heater [24,25] or a thermoelectric (Peltier) device [26] under the sample. The latter is the more versatile solution, since driving current in the opposite direction through the Peltier device results in cooling. In either case, the temperature at the sample must be monitored with a thermocouple or similar, and the heater should ideally be controlled via a proportional-integral-derivative (PID) algorithm.The first temperature-controlled SSI-STM study was reported by English and Hipps, who imaged coronene at the heptanoic acid/Au(111) interface at temperatures up to 558C. [24] This early work established a proof-of-principle, and has since been followed by examples of temperature control in SSI-STM designed to systematically elucidate the energetics of SSI self-assembly.In an elegant illustration of the principle of closest packing, [27,28] Marie et al. showed that in increasing from room temperature to 508C, hexakis(n-dodecyl)-perihexabenzocoronene (HBC-C 12 ) at the n-tetradecane/Au(111) interface undergoes successive, irreversible phase transitions that increase its density of packing (Fi...

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Solvent Induced Polymorphism in Supramolecular 1,3,5-Benzenetribenzoic Acid Monolayers

Cited by 213 publications

References 42 publications

Two-Dimensional Nanotemplates as Surface Cues for the Controlled Assembly of Organic Molecules

Two-Dimensional Nanotemplates as Surface Cues for the Controlled Assembly of Organic Molecules

Two-Dimensional 1,3,5-Tris(4-carboxyphenyl)benzene Self-Assembly at the 1-Phenyloctane/Graphite Interface Revisited

Expanding the Scope of Molecular Self-organization Studies through Temperature Control at the Solution/Solid Interface

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