Selecting Two-Dimensional HalogenâHalogen Bonded Self

Article pubs.acs.org/JPCC

Selecting Two-Dimensional Halogen−Halogen Bonded SelfAssembled 1,3,5-Tris(4-iodophenyl)benzene Porous Nanoarchitectures at the Solid−Liquid Interface Fabien Silly* CEA, IRAMIS, SPCSI, Hybrid Magnetic Nanoarchitectures, F-91191 Gif sur Yvette, France ABSTRACT: The self-assembly of the star-shaped 1,3,5tris(4-iodophenyl)benzene molecule is investigated using scanning tunneling microscopy (STM) at the solid−liquid interface. This molecule forms dimers that self-assemble into two-dimensional porous halogen−halogen bonded nanoarchitectures on the graphite surface. STM shows that the structure of the porous organic network can be tailored using different solvents. Neighboring dimers are binded to each other through two iodine···iodine bonds in 1-phenyloctane, whereas 1-octanol solvent leads to the formation of I4 synthons connecting together four molecular dimers. Iodine bonds appear to be a promising alternative to hydrogen bonds to engineer new organic porous structures on surfaces.

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using molecular building blocks having bromine substituents.18,39 For example, Baris et al. engineered on silicone a porous network having hexagonal cavities using star-shaped 1,3,5-tri(4-bromophenyl)benzene molecules.18 However, this structure is not stabilized by halogen···halogen bonds but by halogen···hydrogen bonds instead. On Ag(110) and Cu(111), this molecule forms polymers after dehalogenation at room temperature,40 whereas small networks stabilized by triple halogen bonds are locally observed at low temperature on Cu(111) and Ag(111). In comparison with a bromine substituent, the two-dimensional self-assembly of building blocks having an iodine (I) substituent has been barely investigated.41−44 Three-dimensional organic architectures have been realized taking advantage of the halogen bonding between iodine atoms and N, I, Cl, Br, and O atoms, for example.45 However, interaction of a molecular iodine atom with other molecular substituents on surfaces is still unclear. One of the reasons is that partial iodine dissociation usually occurs when molecules are deposited on the metal surface.33 This phenomenon can be exploited to generate covalently bonded organic nanoarchitectures, but the large number of defects generated during the process is usually preventing the formation of large-scale highly organized two-dimensional structures.46 In addition to intermolecular interactions, molecule−solvent interaction is also a key parameter that can drastically modify intermolecular binding in solution or at the solid−liquid interface.11,47,48 The influence of the solvent on the two-dimensional self-assembly of iodine-based organic building blocks at the solid/liquid interface still remains obscure.

ngineering complex two-dimensional (2D) porous organic nanoarchitectures is the focus of recent research interest.1−11 Permanent nanoporosity can be exploited after subsequent functionalization12 for developing novel nanostructured materials dedicated to catalysis, gas storage, selective ion exchange, high density data storage, etc. Molecular selfassembly offers a unique direction for the fabrication of twodimensional (2D) organic nanoarchitectures. These structures can be tailored at the nanometer scale by exploiting intermolecular interactions.6,8 In order to create porous nanoarchictures, strong molecule−molecule bindings are required to stabilize organic open networks and to thus prevent the formation of close-packed structures. Hydrogen-bond (H-bond) is a widely used interaction to achieve the formation of organic structures because of the strength,13 the high selectivity, and the high directionality of this binding.14−17 Single18−21 and multicomponent6,22−26 porous nanoarchitectures have already been produced taking advantage of intermolecular H-bonding. For example, the 1,3,5tris(4-carboxyphenyl)benzene molecule is a star-shaped molecule having a carboxylic group as an end-substituent and it has been observed to self-assemble into hydrogen-bonded porous structures on surfaces.27−29 The halogen bond (X-bond) appears to be an appealing alternative to hydrogen bond to tailor molecular self-assembly.30−35 The halogen bond is expected to be highly directional, and its binding geometry can adopt a few configurations.18,36,37 These characteristics open up new opportunities for tailoring molecular self-assembly and for therefore engineering novel organic structures. Rosei’s group succeeded in creating close-packed 2D X-bonded layers using thiophene-based semiconducting organic.38 However, reports describing the formation of stable two-dimensional halogen-bonded porous organic structures are rare. Halogenbonded self-assembled nanoarchitectures are usually fabricated © 2013 American Chemical Society

Received: June 11, 2013 Revised: July 25, 2013 Published: July 31, 2013 20244

dx.doi.org/10.1021/jp4057626 | J. Phys. Chem. C 2013, 117, 20244−20249

The Journal of Physical Chemistry C

Article

In this paper, we investigate the self-assembly of 1,3,5-tris(4iodophenyl)benzene molecules at the 1-phenyloctane/graphite interface as well as the 1-octanol/graphite interface. 1Phenyloctane is a solvent having a low dielectric constant in comparison with 1-octanol. Scanning tunneling microscopy (STM) reveals that molecules form dimers, which self-assemble into halogen···halogen bonded porous nanoarchitectures, whose structure differs depending on the solvent used. The solvent appears to drastically modify the geometry of interdimer iodine···iodine bonds, leading to the formation of different organic nanoarchitectures on the graphite surface. Solutions of 1,3,5-tris(4-iodophenyl)benzene (90%, Aldrich) in 1-phenyloctane (Aldrich) and 1-octanol (Acros) were prepared. A droplet of the solution was then deposited on a graphite substrate. STM imaging of the samples was performed at the liquid−solid interface using a Pico-SPM (Molecular Imaging, Agilent Technology) scanning tunneling microscope. The surfaces were imaged using STM 1 h after molecular deposition. Cut Pt/Ir tips were used to obtain constant current images at room temperature with a bias voltage applied to the sample. STM images were processed and analyzed using the application FabViewer.49 The chemical structure of the 1,3,5-tris(4-iodophenyl)benzene molecule is presented in Figure 1. This 3-fold

Figure 1. Scheme of the 1,3,5-tris(4-iodophenyl)benzene (C21H15I3) dimer building block. Carbon atoms are gray, iodine atoms purple, and hydrogen atoms white.

symmetry molecule is a star-shaped molecule. The molecular skeleton consists of a central benzene ring connected to three peripheral 4′-iodophenyl groups. The molecule is expected to form dimers on surfaces, as it was observed in the case of 1,3,5tri(4′-bromophenyl)benzene molecules.18 The molecular dimer is composed of two molecules rotated by 180° with respect to each other, as represented in Figure 1. The dimer is stabilized by two I···H bindings between neighboring molecules. The STM image in Figure 2a shows the graphite surface after deposition of a droplet of 1,3,5-tris(4-carboxyphenyl)benzene molecules in 1-phenyloctane. Molecules self-assembled into a large-scale 2D porous organic nanoarchitecture, Figure 2a. A high resolution STM image is presented in Figure 2b. As a guide for the eyes, molecules have been colored in red, yellow, blue, and green colors. The STM image shows the domain boundary between a molecular network composed of blue and red molecules and a network composed of green and yellow molecules, respectively. The green and yellow molecules are forming dimers (Figure 1), as well as the red and blue molecules. Molecular dimers are connected to each other through halogen···halogen bonds; i.e., single I···I bonds are only formed between molecules of the same color, except at the domain boundary. The cavities formed by two molecular dimers have a stretched hexagonal shape, Figure 2d. The unit

Figure 2. STM image of the 1,3,5-tris(4-iodophenyl)benzene selfassembled porous network at the 1-phenyloctane/graphite interface: 24 × 20 nm2, Vs = 0.70 V, It = 9 pA (a); 15 × 15 nm2, Vs = 0.70 V, It = 10 pA (b). Molecules have been colored in red, yellow, blue, and green in the STM image in part b. (c) Model of the organic network. The unit cell is represented with dashed black lines. Molecules are schematically represented by red, yellow, blue, and green stars. The network cavity shape is represented in gray in part d, and the cavity formed at the domain boundary is represented in gray in part e.

cell of this porous nanoarchitecture is represented with black dashed lines in Figure 2c. The network unit cell of this porous structure is a parallelogram with 2.0 ± 0.2 and 2.4 ± 0.2 nm unit cell constants and an angle of ∼60° between the axes. The unit cell is composed of two molecules. At the boundary between red−blue and yellow−green molecular domains, molecular dimers are also connected through halogen···halogen 20245



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for the eyes, molecules have also been colored in red, yellow, blue, and green colors in the STM image, Figure 3b. It appears that the molecular dimer is the building block of a single domain covering entirely the graphite surface. Dimers are formed by paired green−yellow molecules and paired red−blue molecules, respectively. The nanoarchitecture observed in Figure 3b is composed by an alternation of vertical red−blue molecular dimer rows with green−yellow molecular dimer rows. The model of this structure is presented in Figure 3c. Molecular dimers are connected through I···I bonds along dimer rows. Interestingly, dimers of neighboring rows are also connected through I···I bonds. The unit cell of this porous nanoarchitecture is represented with black dashed lines in Figure 3c; it has a shape of a rectangle with 3.4 ± 0.3 and 2.7 ± 0.3 nm lattice constants and an angle of ∼90° between the axes. The unit cell is composed of four molecules. The network cavities are formed by three molecular dimers, and they have a stretched pentagonal shape, as illustrated in Figure 3d,e. This nanoarchitecture possesses chiral cavities. The two enantiomeric cavity shapes are represented in light gray color in the model shown in Figure 3d,e. These cavities are experimentally observed in Figure 3b. STM images reveal that 1,3,5-tris(4-iodophenyl)benzene molecules self-assemble into porous structures at the liquid− graphite interface. The structure of the two-dimensional 1,3,5tris(4-iodophenyl)benzene nanoarchitectures is solvent dependent. The molecular unit cell is composed of two molecules when 1-phenyloctane is used as solvent. In contrast, the network unit cell is composed of four molecules when 1octanol solvent is used. It should be noticed that the solvent molecule is not a building block of the organic layer covering the graphite surface. The 1,3,5-tris(4-iodophenyl)benzene dimer appears to be the unique molecular building block of the two organic nanoarchitectures observed in Figures 2 and 3. Neighboring dimers are binded through I···I bonds. However, there are manifest differences in interdimer binding depending on the solvent used. Iodine is one element belonging to the halogens. This atom is in general highly polarizable; i.e., there is a nonspherical charge distribution and an electrostatic potential in the halogen−carbon bond, Figure 4a. Therefore, the charge distribution around the halogen (X) atom in an X−C group is anisotropic. The polar region around the halogen atom has a

bonds; i.e., blue (red) molecules are connected to green (yellow) molecules through single I···I bonds, respectively. It results in the formation of a second type of nearly hexagonal cavities at the domain boundary. These cavities are formed by four molecular dimers, Figure 2e. The STM image in Figure 3a shows the graphite surface after deposition of a droplet of 1,3,5-tris(4-carboxyphenyl)benzene molecules in 1-octanol. The molecules also self-assemble into a porous structure at the 1-octanol/graphite interface, Figure 3a,b. However, this nanoarchitecture differs from the one observed at the 1-phenyloctane/graphite interface. As a guide

Figure 3. STM image of the 1,3,5-tris(4-iodophenyl)benzene selfassembled porous network at the 1-octanol/graphite interface: (a) 22 × 20 nm2; (b) 13 × 10 nm2. Vs = 0.79 V, It = 580 pA. Molecules have been colored in red, yellow, blue, and green in the STM image in part b. (c) Model of the organic network. The unit cell is represented with dashed black lines. Molecules are schematically represented by red, yellow, blue, and green stars. The two enantiomeric cavity shapes are represented in gray in parts d and e.

Figure 4. (a) Illustration of the charge distribution in the I−C bond. The purple (gray) ball is the iodine (carbon) atom. (b) Scheme of a type-I halogen bond. (c) Scheme of a type-II halogen bond. (d) Scheme of iodine···iodine binding (I4 synthon) observed in the organic nanoarchitecture at the 1-octanol/graphite interface. 20246



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of polar media on the charge distribution of X-bonds, but this is beyond the scope of this paper. To summarize, scanning tunneling microscopy showed that star-shaped 1,3,5-tris(4-iodophenyl)benzene molecules form dimers at the liquid/graphite interface and self-assembled into two different porous nanoarchitectures depending of the solvent used. At the 1-phenyloctane/graphite interface, molecular dimers are connected through charge polarization induced iodine···iodine bonds only, whereas van der Waals type as well as polarization induced iodine···iodine bonds are observed at the 1-octanol/graphite interface. It results in the formation of molecular I4 synthons in 1-octanol. These observations show that halogen···halogen bonds are promising alternatives to hydrogen bonds to create self-assembled porous nanoarchitectures with cavities having different shape and size on surfaces. This opens up new opportunities for tailoring molecular self-assembly and for engineering porous organic nanoarchitectures having sophisticated structures. Noncovalent 2D porous organic nanoarchitectures can be, for example, used to trap organic species52−55 or metal atoms56−58 to build multicomponent or hybrid nanoarchitectures and also be used to modify the electronic properties of conducting surfaces.3,23,59

positive polarization (+) along the X−C axis, whereas the polar region perpendicular to this axis has a negative polarization (−), as represented in the scheme, Figure 4a. Bui et al. previously classified the different types of C−X···X−C bonds depending on the angle between X−C groups.50 The type-I interaction is of van der Waals type. In that case, the intermolecular binding geometry has a crystallographic inversion center and molecular X−C groups are aligned in the same direction,50 Figure 4b. The type-II interaction is an attractive interaction between the nucleophilic (−) and electrophilic (+) areas of halogen atoms. In that case, the intermolecular binding geometry usually possesses crystallographic screw axes and glide planes. The angle between the molecular X−C group axis is ∼90−120°. The geometry of an iodine type-II bond is represented in Figure 4c. In 1-phenyloctane, the 1,3,5-tris(4-iodophenyl)benzene dimers are connected through the I···I bond represented in Figure 4c. The angle between the I−C axis of binded molecules is ∼120°. This is, for example, the geometry of the binding between red molecules in Figure 2. This intermolecular binding corresponds to the type-II halogen binding. No other interdimer I···I binding type is observed in the molecular network or at the domain boundary at the 1-phenyloctane/ graphite interface. Molecular dimer binding at the 1-octanol/graphite interface is drastically different. STM images reveal that each intermolecular dimer binding involves four iodine atoms. The scheme illustrating the binding between blue, green, yellow, and red molecules, experimentally observed in Figure 3, is represented in Figure 4d. In this binding, four iodine atoms are almost aligned (see dotted line in Figure 4d) and form a X4 synthon. The angle between the I−C axes of blue and green (or yellow and red) molecules is ∼110°. It therefore corresponds to a type-II binding, Figure 4c. In comparison, the I−C axes of green and yellow molecules are aligned. It corresponds to a type-I binding, Figure 4b, according to ref 50. The 1,3,5-tris(4iodophenyl)benzene self-assembled nanoarchitecture is therefore stabilized not only by van der Waals iodine···iodine bonds (type I) but also by charge-polarization-induced iodine···iodine bonds (type II). This linear X4 synthon resulting from the binding of four iodine atoms is stabilized by two type-II halogen···halogen bonds and one type-I halogen···halogen bond. No other idodine-based synthon is observed in the 1,3,5-tris(4-iodophenyl)benzene nanoarchitecture at the 1octanol/graphite interface. Duarte et al. calculated that strong halogen bonds cause rearrangement in electronic density distribution on all the atoms forming the binding.51 This effect originates from the interpenetration between the electron clouds of the atoms. 1Phenyloctane appears to favor 2D structures stabilized by Xbond type II. As this binding results from charge polarization, and is expected to be strong, the dipole moment of the I−C groups of the molecules is expected to be affected by the I···I binding. In contrast, 1-octanol appears to favor 2D structures stabilized not only by type-II bindings but also by type-I bindings. As type-I binding is of van der Waals type, the local dipolar moment of the molecule is expected to be weakly affected. It appears therefore that the total charge distribution of the structures observed in Figures 2 and 3 is not equivalent. This may originate from the different dielectric constant of the solvents; i.e., 1-octanol has a higher dielectric constant than 1phenyloctane, and 1-octanol is in fact considered to be a polar solvent. Calculations are required for elucidating the influence

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Phone: +33(0)169088019. Fax: +33(0)169088446. Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS The research leading to these results has received funding from the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013)/ERC grant agreement no. 259297.

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