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Temperature-Dependent Structure of Two-Dimensional Hybrid NaClPTCDI Nanoarchitectures on Au(111) David Peyrot and Fabien Silly* TITANS, SPEC, CEA, CNRS, Université Paris-Saclay, CEA Saclay, F-91191 Gif sur Yvette, France ABSTRACT: PTCDI molecules and NaCl self-assemble on the Au(111) surface to form two-dimensional porous hybrid nanoarchitectures. Scanning tunneling microscopy (STM) reveals that temperature can drastically influence the structure of these nanoarchitectures. A PTCDI-NaCl flower structure is created after codeposition onto a surface at 20 °C. The molecules and the ionic compound form a mesh nanoarchitecture after annealing at 100 °C, a ladder nanoarchitecture after annealing at 140 °C, and a chain nanoarchitecture after annealing at 150 °C. Close-packed PTCDI islands surrounded by single PTCDI-NaCl chains are observed after annealing at 160 °C. STM shows that NaCl interacts selectively and locally with molecular N-H groups. This organic−ionic interaction is highly directional. A temperature increase appears to first favor the ordering of PTCDI and NaCl compound and then to favor the formation of higher density structures. At high temperature, the ionic compound desorbs from the surface. This combination of organic and ionic compounds is a promising system to engineer novel 2D materials with a tunable internal structure.

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INTRODUCTION Engineering porous nanostructures on surfaces is a challenge in nanosciences.1 Porous nanoarchitectures can be used as host structures to trap foreign species2−11 or to modify the electronic properties of conductive surfaces.12−19 Molecular self-assembly is an efficient method to create large porous networks on flat metal surfaces. Strong and directional intermolecular interactions are usually required to stabilize porous structures and therefore prevent molecules from forming close-packed arrangements. Porous organic nanoarchitectures have been, for example, successfully achieved exploiting selective and directional hydrogen2,20−28 and halogen bondings29−36 as well as metal−ligand interactions.37−39 Recent observations reveal that molecules can self-assemble with alkali metal ions and ionic compounds for hybrid nanoarchitectures. The ionic species are not always resolved in the scanning tunneling (STM) images. It has been proposed that potassium and sodium adatoms interact with molecular oxygen groups.40−42 Wäckerlin et al. reported that alkali halides interact with molecular nitrogen groups.43 Shimizu et al. observed that molecular arrangement is modified after adding NaCl on Cu(111).44 They suggest that the ionic compound is intercalated between the molecules and the metal surface. NaCl sublimated in vacuum on a Au(111) surface leads to the formation of two-dimensional crystalline islands.45,46 We recently showed that NaCl interacts with the N-H groups of 3,4,9,10-perylenetetracarboxylic diimide (PTCDI) molecules after sequential deposition of organic and ionic compound on a Au(111) surface.47 The molecule−ionic compound interaction appears to be directional and selective. Here, we investigate the interaction of PTCDI molecules with NaCl when the two compounds are simultaneously codeposited on a Au(111) surface. Scanning tunneling microscopy (STM) in ultrahigh vacuum reveals that © 2017 American Chemical Society

codeposition of PTCDI molecules and NaCl leads to the formation of complex 2D hybrid nanoarchitectures. Five different 2D hybrid nanoarchitectures can be created at specific temperatures.

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METHODS

Experiments were performed in an ultra-high-vacuum (UHV) chamber at a pressure of 10−8 Pa. The Au(111) surface was sputtered with Ar+ ions and then annealed in UHV at 600 °C for 1 h. PTCDI molecules (Figure 1a) and NaCl (Figure 1b) were evaporated at 250 and 390 °C, respectively, on the gold surface kept at room temperature. Less than 30% of the gold surface was covered with organic and ionic compounds. Cut Pt/Ir tips were used to obtain constant current STM images at room temperature with a bias voltage applied to the sample. STM images were processed and analyzed using the homemade FabViewer application.48

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RESULTS PTCDI and NaCl Arrangement at Room Temperature. A model of a PTCDI molecule and NaCl is presented in Figure 1a,b, respectively. As a guide for the eyes, the local charges in the PTCDI skeleton and the NaCl dimer are represented. These local charges are driving PTCDI self-assembly through hydrogen bonding24 and NaCl crystalline arrangement through ionic interactions. Figure 1c shows an STM image of the PTCDI self-assembly on the Au(111) surface at room temperature. This canted structure has been described in detail by Mura et al.24 The Received: June 19, 2017 Revised: August 24, 2017 Published: August 29, 2017 20986

DOI: 10.1021/acs.jpcc.7b05998 J. Phys. Chem. C 2017, 121, 20986−20993

Article

The Journal of Physical Chemistry C

Figure 1. (a) Scheme of PTCDI molecule. Gray balls are carbon atoms, red balls are oxygen atoms, white balls are hydrogen atoms, and blue balls are nitrogen atoms. (b) Scheme of NaCl unit cell. Blue balls are chloride, and green balls are sodium atoms. (Right) NaCl dipole. “+” and “−” highlight the local positive and negative charge distribution in the PTCDI skeleton and the NaCl dipole. (c) STM image of the PTCDI self-assembly, 6 × 6 nm2, Vs = +1.3 V, It = 180 pA. (d) STM image of a NaCl layer, 5 × 3 nm2, Vs = +0.4 V, It = 106 pA. The unit cells have been superimposed to the STM images in (c) and (d).

network unit cell of this hydrogen-bonded structure is a parallelogram with 1.7 and 1.3 nm unit cell constants and an angle of 87° between the axes. Figure 1d shows an atomically resolved STM image of a NaCl island. The closest distance between two bright spots in the NaCl layer is 4.0 Å. This corresponds to the closest separation of one atomic species in the NaCl(001) surface. These bright spots in the NaCl STM image are attributed to the Cl− anions.49,50 PTCDI-NaCl Flower Structure after Codeposition on a Surface at 20 °C. Figure 2 shows STM images of the Au(111) surface after simultaneous codeposition of PTCDI and NaCl onto a surface at 20 °C. Flat square and rectangular NaCl islands can be observed in the large-scale STM image in Figure 2a. These islands have almost straight step edges, and the angle between the step edges is usually ∼90°. These NaCl crystalline islands are coexisting with PTCDI domains. A high-resolution STM image of the PTCDI domains is presented in Figure 2b. The STM image reveals the organic domains are composed of PTCDI molecules and NaCl multimers. The NaCl multimers appear as bright spots in the STM image. NaCl multimers are surrounded by PTCDI molecules, leading to the formation of a hybrid porous “flower” network. The center of the flower pattern is composed of NaCl multimers, whereas the PTCDI molecules are the petal of the pattern. The PTCDI molecules appear to be bonded to the NaCl multimer through their imide groups. STM images of the flower structure with 1−8 spot NaCl multimers are presented in Figure 2c−k. It should be noticed that the NaCl multimers do not adopt the square packing of the bulk NaCl (Figure 1d) that is observed in the NaCl islands (Figure 2b). Figure 3a shows an STM image of a PTCDI-NaCl periodic pattern that is locally observed at room temperature. It consists

Figure 2. STM images of the PTCDI-NaCl domains after annealing at 100 °C, (a) 40 × 35 nm2, Vs = +1.3 V, It = 180 pA, (b) 17 × 17 nm2, Vs = +1.3 V, It = 100 pA, (c) 4 × 4 nm2, (d) 4 × 3 nm2, (e) 5 × 3 nm2, (f) 5 × 4 nm2, (g) 5 × 5 nm2, (h) 5 × 5 nm2, (i) 5 × 4 nm2, (j) 5 × 5 nm2, (k) 5 × 5 nm2. (c, d) Vs = +1.9 V, It = 80 pA. (e−k) Vs = +1.3 V, It = 100 pA.

of the “X” building blocks composed of NaCl clusters composed of two Cl atoms surrounded by four PTCDI molecules. This X-block is represented with green PTCDI molecules and green circles corresponding to the NaCl cluster in Figure 3b, dotted rectangle. The angles between neighboring molecules are 60° and 120°. The X-blocks are aligned and 20987


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Figure 3. (a) STM images of a PTCDI-NaCl periodic pattern locally observed at room temperature, 7 × 3 nm2, Vs = +1.3 V, It = 100 pA. (b) Model. The pattern observed in (a) is highlighted by a dashed blue rectangle in (b). The Cl atom positions in the NaCl clusters are represented by green, blue, and purple circles.

bonded through NaCl···PTCDI bonds. Slightly larger NaCl clusters are trapped in between two neighboring X-blocks. These NaCl clusters are composed of six bright spots (corresponding to six Cl atoms); i.e., four bright spots are arranged into a square and two additional bright spots are localized symmetrically facing the middle of the NaCl square. As a guide for the eyes, Cl atom positions of this NaCl cluster are highlighted by blue circles in Figure 3b, dotted rectangle. This larger NaCl cluster appears to not be bonded to the NaClPTCDI X-blocks. This arrangement is thus a guest−host structure with the NaCl-PTCDI X-block as the building block of the host structure, whereas the larger NaCl clusters are the hosted species. Despite that no long order arrangement is observed at room temperature, one can predict the 2D nanoarchitectures corresponding to the assembly of these building blocks, as it was done by Liang et al.51 The model of this structure is presented in Figure 3b, where the Cl atoms of the NaCl clusters are represented by purple circles. An STM image of a crystalline NaCl island surrounded by PTCDI molecules is presented in Figure 4. The STM image

Figure 4. STM image of a NaCl island in the PTCDI-NaCl domain, 10 × 10 nm2, Vs = +1.3 V, It = 180 pA.

Figure 5. STM image of the PTCDI-NaCl nanoarchitecture after codeposition of PTCDI and NaCl on Au(111)-(22 × √3) at room temperature and a post-annealing at 100 °C, (a) 48 × 40 nm2, Vs = +1.3 V, It = 180 pA, (b) 18 × 10 nm2, Vs = +1.3 V, It = 180 pA. (c) Model of the mesh PTCDI-NaCl nanoarchitecture. NaCl dipoles are represented by purple circles. (d) Model of the PTCDI···NaCl··· PTCDI stick on Au(111) (side view).

shows that the PTCDI molecules are preferentially bonded to the NaCl island through their imide groups (molecule short side), as it is also observed in the other hybrid structures presented in Figure 2b,k. These molecules are preferentially arranged side-by-side. Porous Mesh Nanoarchitecture after Annealing at 100 °C. Figure 5a shows a large-scale STM image of the surface after annealing at 100 °C. PTCDI molecules and NaCl form now a well-organized large two-dimensional porous network. A high-resolution STM image of this structure is presented in Figure 5b. NaCl appears now as a single round spot, suggesting it corresponds to a single NaCl dimer. The round spots thus

highlight the position of the Cl atoms in the NaCl dimers. The building block of this nanoarchitecture is a straight PTCDI··· NaCl···PTCDI stick (Figure 5d). The NaCl dimer is localized in between the two molecules, and it is facing the molecular imide group. The symmetrical aspect of this block in the STM images indicates that the NaCl dimer is standing vertically on the gold surface. This hybrid building block is highlighted by 20988


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2.1 nm, and the periodicity along the chain is 1.5 nm.The STM images presented in Figure 6b are, however, revealing that neighboring parallel PTCDI-NaCl chains can be shifted along their main axis. It results in the appearance of different local unit cells (highlighted by dashed black parallelograms in the three STM images presented in Figure 6b). The network unit cell of the ladder structure is a parallelogram with 1.5 and ∼2.1 nm unit cell constants and the angle between the axes varies between 90° and 70°. The model of the ladder nanoarchitecture with the unit cell angle of 70° is presented in Figure 6c. Figure 7 shows an STM image of the edge of a crystalline NaCl island after annealing at 140 °C. PTCDI molecules are

dotted ellipses in the STM image in Figure 5b. Neighboring PTCDI···NaCl···PTCDI sticks are almost perpendicular in this “mesh” nanoarchitecture (Figure 5b). The angle between neighboring sticks is ∼80°. Neighboring PTCDI-NaCl sticks appear to be preferentially attached through N−H···O and H··· O hydrogen bonds between neighboring PTCDI molecules. The network unit cell of this porous structure is a rectangle with 2.3 and 2.5 nm unit cell constants and an angle of ∼90° between the axes. The model of this porous structure is presented in Figure 5c. Porous Ladder Nanoarchitecture after Annealing at 140 °C. Figure 6a shows an STM image of the PTCDI-NaCl

Figure 7. STM image of the edge of a NaCl island after codeposition of PTCDI and NaCl on Au(111)-(22 × √3) at room temperature and a post-annealing at 140 °C, 7 × 10 nm2, Vs = +1.2 V, It = 110 pA.

perpendicular to the NaCl island, as it was observed at lower temperature in Figure 4. These PTCDI molecules are, however, now not adopting a close-packed side-by-side arrangement. The molecules are now well separated. These molecules are connected on one side to the NaCl island and to the other side to a perpendicular PTCDI-NaCl chain that is surrounding the NaCl island. This leads to the formation of a ladder structure around the NaCl island. Porous Chain Nanoarchitecture after Annealing at 150 °C. Figure 8 shows an STM image of the PTCDI-NaCl arrangement after annealing the surface at 150 °C. PTCDI molecules and NaCl self-assemble now into a “chain” nanoarchitecture. This structure is composed of parallel PTCDI···NaCl straight chains. Neighboring PTCDI-NaCl chains are separated by PTCDI molecules. The molecules are not perpendicular, like in the ladder structure (Figure 6), but they are rotated by ∼12° in comparison with the PTCDI chain axis. The network unit cell of this porous structure is a parallelogram with 1.5 and 1.7 nm unit cell constants and an angle of ∼74° between the axes. The model of this nanoarchitecture is presented in Figure 8b. The parallel PTCDI···NaCl chains are highlighted by dashed green ellipses. Decorated PTCDI Islands after Annealing at 160 °C. Figure 9 shows the STM image of the PTCDI-NaCl arrangement after annealing the Au(111) surface at 160 °C. The STM image reveals that the PTCDI molecules now form a close-packed PTCDI island surrounded by PTCDI-NaCl chains. The PTCDI-NaCl chains are composed of aligned PTCDI···NaCl dimers as observed in the chain structure in Figure 8. The PTCDI molecules adopt a side-by-side arrangement inside the island. This molecular arrangement has been previously described in ref 52. A model of one of the

Figure 6. STM image of the PTCDI-NaCl ladder nanoarchitecture after codeposition of PTCDI and NaCl on Au(111)-(22 × √3) at room temperature and a post-annealing at 140 °C, (a) 12 × 7 nm2, Vs = +1.3 V, It = 180 pA, (b) 5 × 6 nm2, Vs = +1.3 V, It = 180 pA. Local unit cells (dashed black lines) have been superimposed to the STM images. (c) Model of the PTCDI-NaCl ladder nanoarchitecture observed in (a). NaCl dipoles are represented by purple circles, and NaCl-PTCDI chains are surrounded by green ellipses. The unit cell is represented by a black parallelogram.

assembly on Au(111) after annealing at 140 °C. PTCDI and NaCl now form a porous ladder nanoarchitecture. This structure is composed of parallel PTCDI···NaCl straight chains (NaCl dimer appears as a round spot in the STM image). Neighboring PTCDI-NaCl chains are separated by single PTCDI molecules. These PTCDI molecules are nearly perpendicular to the chain. These perpendicular molecules are not directly facing the NaCl dimers of the PTCDI-NaCl chains. The molecules appear to form N-H···O and H···O hydrogen bonds with the PTCDI molecules of the neighboring chains. The separation of the straight PTCDI-NaCl chains is 20989


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Figure 9. (a) STM image of the PTCDI-NaCl nanoarchitecture after codeposition on Au(111)-(22 × √3) at room temperature and postannealing at 160 °C, 40 × 40 nm2, Vs = +1.8 V, It = 0.2 nA, (b) 22 × 12 nm2, Vs = +1.8 V, It = 0.2 nA. (c) Model of a PTCDI island with PTCDI-NaCl edges. NaCl dipoles are represented by purple circles.

NaCl dimers form parallel PTCDI-NaCl chains. These chains are separated by nearly perpendicular PTCDI molecules after annealing at 140 °C (Figure 6), whereas the angle is 12° after annealing at 150 °C (Figure 8). It should be noticed that there is no sharp transition between the different structures. The flower structure is, for example, very locally observed after annealing at 100 °C, and the mesh structure is still locally observed after annealing at 140 °C. NaCl is desorbing from the surface after annealing at 160 °C. The surface is then covered with compact PTCDI islands surrounded with PTCDI-NaCl chains (Figure 9). STM images reveal that the PTCDI N-H group strongly interacts with NaCl. This interaction is observed in every PTCDI-NaCl nanoarchitecture. Bulk sodium chloride is an ionic crystal with cubic symmetry. The NaCl structure is composed of dimers consisting of a positively charged sodium ion, Na+, and a negatively charged chloride ion, Cl− (Figure 1b). The PTCDI skeleton has a non-uniform internal charge distribution. The oxygen atoms of the imide groups carry a negative partial charge, whereas the N-H groups carry a positive partial charge (Figure 1a). The complementary charge distribution of the NaCl dimer and PTCDI appears to be at the origin of the long-range self-assembly of these two building blocks. This interaction is directional and selective. Surface temperature appears to drastically affect PTCDI and NaCl ordering. The unit cell parameters and the density of each hybrid nanoarchitecture are presented in Table 1. The table indicates that, from 20 to 140 °C, the molecular density of the PTCDI-NaCl nanoarchitectures is quite constant. The ordering of the structure is, however, changing. At room temperature,

Figure 8. (a) STM image of the PTCDI-NaCl nanoarchitecture after codeposition on Au(111)-(22 × √3) at room temperature and postannealing at 150 °C, 10 × 10 nm2, Vs = +1.9 V, It = 0.2 nA. (b) Model of the chain nanoarchitecture. NaCl dipoles are represented by purple circles.

island structures is presented in Figure 9. The network unit cell of this PTCDI close-packed structure is a parallelogram with 1.5 and 0.8 nm unit cell constants and an angle of ∼78° between the axes.

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DISCUSSION STM reveals that hybrid organic−ionic nanoarchitectures can be achieved by simultaneously codepositing PTCDI molecules and NaCl on Au(111). The structure of theses nanoarchitectures appears to be highly tunable with surface temperature. At room temperature, NaCl and PTCDI selfassemble into a flower structure. NaCl forms tiny clusters surrounded by PTCDI molecules. This structure is quite defective. This is due to the inhomogeneity of the NaCl cluster size and shape. After annealing at 100 °C, a well ordered PTCDI-NaCl mesh arrangement appears on the surface. In this structure, each PTCDI molecule is attached to one NaCl dimer through a N-H···NaCl bond. The other side of the molecules is in comparison connected to a neighboring PTCDI molecule through hydrogen bonds. The building block of this structure is a PTCDI-NaCl-PTCDI stick. The NaCl dimer appears to stand vertically on the surface. At higher temperature, the PTCDI and 20990


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Table 1. Lengths (in Å) of the Two Lattice Vectors (A1 and A2) and the Angle θ between Them (in Degrees) for the Different NaCl-PTCDI Nanoarchitectures

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the PTCDI-NaCl arrangement is hexagonal and is quite defective. A temperature increase appears to favor the formation of the linear PTCDI-NaCl arrangement (sticks at 100 °C and chains at higher temperatures). Above 140 °C, the density of the PTCDI-NaCl arrangement is increasing. The PTCDI molecules separating the PTCDI-NaCl chains are perpendicular to the chains at 140 °C, but they are rotated by 12° after annealing at 150 °C. This leads to a increase of density of 20%. NaCl is desorbing from the surface after annealing at 160 °C. Only remain on the surface PTCDI-NaCl chains at the edge of compact PTCDI island. This structure is not porous anymore.

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CONCLUSION In summary, we used scanning tunneling microscopy to investigate the interaction between PTCDI molecules and NaCl in vacuum. STM reveals that PTCDI and NaCl selfassemble on Au(111) and form hybrid two-dimensional nanoarchitectures. The NaCl dimers appear to selectively and locally interact with the PTCDI N-H group. The NaCl-PTCDI binding appears to be highly directional and selective. The strength of this binding is strong enough to stabilize the porous nanoarchitecture at room temperature. By changing the annealing conditions after PTCDI and NaCl depositions, the structure of the NaCl-PTCDI nanoarchitectures can be modified. This system is a promising alternative to metal− organic and multicomponent organic arrangements to engineer novel adjustable nanostructures on surfaces.

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REFERENCES

AUTHOR INFORMATION

Corresponding Author

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

Fabien Silly: 0000-0001-6782-9268 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. D.P. thanks the CEA Saclay for the Ph.D. fellowship. The authors also thank the French National Research Agency (project Magic Carpet, ANR 12 JS10 010 01) for financial support. 20991


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The Journal of Physical Chemistry C carboxylic Diimide Nanoarchitectures. J. Mater. Chem. C 2013, 1, 4536−4539.

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