Surface-Mediated Catalytic Dechlorination and Spin-State Modulation of ClFePc on Au(111)
2024; Chinese Chemical Society; Linguagem: Inglês
10.31635/ccschem.024.202404417
ISSN2096-5745
AutoresJie Li, Chenyang Yuan, Yang He, Zhen Xu, Haoyang Pan, Shuai Lu, Yudi Wang, Mingjun Zhong, Xin Li, Shimin Hou, Qian Shen, Kai Wu, Yajie Zhang, Song Gao, Yongfeng Wang,
Tópico(s)Advanced Materials Characterization Techniques
ResumoOpen AccessCCS ChemistryRESEARCH ARTICLES6 Aug 2024Surface-Mediated Catalytic Dechlorination and Spin-State Modulation of ClFePc on Au(111) Jie Li, Chenyang Yuan, Yang He, Zhen Xu, Haoyang Pan, Shuai Lu, Yudi Wang, Mingjun Zhong, Xin Li, Shimin Hou, Qian Shen, Kai Wu, Yajie Zhang, Song Gao and YongFeng Wang Jie Li Center for Carbon-Based Electronics and Key Laboratory for the Physics and Chemistry of Nanodevices, School of Electronics, Peking University, Beijing 100871 , Chenyang Yuan Center for Carbon-Based Electronics and Key Laboratory for the Physics and Chemistry of Nanodevices, School of Electronics, Peking University, Beijing 100871 , Yang He *Corresponding authors: E-mail Address: [email protected] E-mail Address: [email protected] E-mail Address: [email protected] School of Material and New Energy, South China Normal University, Shanwei 516600 , Zhen Xu Spin-X Institute, School of Microelectronics, South China University of Technology, Guangzhou 511442 , Haoyang Pan Spin-X Institute, School of Microelectronics, South China University of Technology, Guangzhou 511442 , Shuai Lu Center for Carbon-Based Electronics and Key Laboratory for the Physics and Chemistry of Nanodevices, School of Electronics, Peking University, Beijing 100871 , Yudi Wang Center for Carbon-Based Electronics and Key Laboratory for the Physics and Chemistry of Nanodevices, School of Electronics, Peking University, Beijing 100871 , Mingjun Zhong Center for Carbon-Based Electronics and Key Laboratory for the Physics and Chemistry of Nanodevices, School of Electronics, Peking University, Beijing 100871 , Xin Li Center for Carbon-Based Electronics and Key Laboratory for the Physics and Chemistry of Nanodevices, School of Electronics, Peking University, Beijing 100871 , Shimin Hou Center for Carbon-Based Electronics and Key Laboratory for the Physics and Chemistry of Nanodevices, School of Electronics, Peking University, Beijing 100871 , Qian Shen Key Laboratory of Flexible Electronics (KLOFE) and Institute of Advanced Materials (IAM), Nanjing Tech University, Nanjing 211816 , Kai Wu BNLMS, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871 , Yajie Zhang *Corresponding authors: E-mail Address: [email protected] E-mail Address: [email protected] E-mail Address: [email protected] Center for Carbon-Based Electronics and Key Laboratory for the Physics and Chemistry of Nanodevices, School of Electronics, Peking University, Beijing 100871 , Song Gao Spin-X Institute, School of Microelectronics, South China University of Technology, Guangzhou 511442 and YongFeng Wang *Corresponding authors: E-mail Address: [email protected] E-mail Address: [email protected] E-mail Address: [email protected] Center for Carbon-Based Electronics and Key Laboratory for the Physics and Chemistry of Nanodevices, School of Electronics, Peking University, Beijing 100871 Cite this: CCS Chemistry. 2024;0:1–8https://doi.org/10.31635/ccschem.024.202404417 SectionsSupplemental MaterialAboutAbstractPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail Interactions between molecules and surfaces are crucial in modern surface science. In particular, surfaces catalyze molecular reactions and modulate molecular spin states. In this article, we investigate the adsorption behaviors and electronic structures of chloro-iron phthalocyanine (ClFePc) on Au(111). Combining ultrahigh vacuum scanning tunneling microscopy experiments with density functional theory calculations, we found indications of surface-catalyzed dechlorination. Our findings reveal that the adsorption behavior of ClFePc is determined by its adsorption direction. ClFePc in the Cl-up (Cl pointing to the vacuum) configuration exhibits stable adsorption on the Au(111) surface. Conversely, the Cl-down (Cl pointing to the substrate) configuration is unstable, resulting in the dissociation of the Cl–Fe bond due to interactions with the Au(111) surface. Through scanning tunneling spectroscopy analysis, we further investigate the Kondo resonance features and spin characteristics. Notably, following dechlorination, the spin-state transitions from S = 3/2 to 1. This study provides profound insights into the surface-molecule interaction and its application in modulating magnetic properties. Download figure Download PowerPoint Introduction The comprehension of adsorption and reactions involving organic molecules on metal surfaces plays a significant role in various research areas like heterogeneous catalysis,1–3 surface synthesis,4–6 and spintronics.7,8 Metal surfaces serve as important modulators of the electronic properties of adsorbed molecules,9,10 potentially facilitating reactions to occur with lower reaction barriers.11,12 Notably, research has discovered that metal surfaces can effectively mediate the dissociation of coordination bonds within metal–organic molecules, particularly nonplanar dipole molecules containing central metal-halogen substituents.1,13–17 For instance, the Cu(111) surface could catalyzed the dissociation of the Cl–Fe bond in FeOEP-Cl, resulting in partial dechlorination.13 Similar reactions have also been observed in analogous nonplanar dipole molecules such as ClB-SubPc and GaClPc.14,15 These reactions provide compelling evidence for surface-induced chemical reactions, which change the adsorption configuration of molecules and significantly influence their electronic states. Notably, for magnetic organic molecules, conformational changes in their ligands triggered by surface interactions can significantly impact their magnetic properties.18–21 Nevertheless, research on the modulation of magnetic characteristics in organic molecules catalyzed by metal surfaces remains relatively sparse.22 ClFePc, a unique magnetic phthalocyanine molecule, stands out as an ideal model for studying metal–organic interface interactions due to its unique electronic and magnetic properties.23–25 This phthalocyanine molecule exhibits a nonplanar structure, distinctively characterized by an axial bond connecting the Cl atom to the central Fe ion. Upon adsorption on a metal surface, ClFePc can adopt two possible configurations: Cl-up and Cl-down.26,27 This distinctive structural aspect offers a versatile platform, enabling the metal surface to modulate both its molecular structure and electronic properties. Consequently, ClFePc emerges as a promising candidate for exploring the catalytic effects of metal surfaces on organic molecules. Herein, based on the catalytic ability of Au(111) for dehalogenation,28,29 we chose Au(111) as a model surface to investigate the adsorption behavior of ClFePc using a combined approach of scanning tunneling microscopy (STM) experiments and density functional theory (DFT) calculations. Our objective was to elucidate the adsorption configuration of ClFePc molecules and the catalytic dissociation process of the Cl–Fe bond. Additionally, we sought to investigate how the Au(111) surface modulates the spin state of the molecule. These revelations will not only enrich our understanding of molecule-surface interactions but also offer new insights into utilizing surface catalysis mechanisms to modulate molecular spin states. Experimental Methods STM characterization and STS measurements All the experiments are carried out in a Unisoku low-temperature STM with a base vacuum of 10−10 Torr at 4.3 K. The Au(111) surface is cleaned by cycles of argon ion sputtering and annealing. The ClFePc molecules are thermally deposited from a homemade tantalum boat at about 500 K. A Pt/Ir tip is used for STM measurements. High-quality scanning tunneling spectroscopy (STS) spectra (dI/dV curves) are recorded through the lock-in amplifier by adding a small sinusoidal modulation 0.5 mV onto the bias voltage. All STM images are processed by the WSxM software.30 Spin-polarized DFT calculations All first-principle calculations are performed based on the spin-polarized framework of DFT as implemented in the Vienna ab initio simulation package code (VASP).31,32 The electron–ion interaction is described by the projector-augmented wave (PAW) method, and the energy cutoff for the plane-wave basis is 500 eV.33 The generalized gradient approximation (GGA) developed by Perdew–Burke–Ernzerhof (PBE) is used to describe the electron exchange and correlation energy.34 The Hubbard U correction is used on the localized 3d orbitals of Fe atom with U = 2 eV and J = 1.0 eV, which is the same as the similar systems.35,36 The long-range dispersion interactions are taken into account using the DFT-D3 (BJ) method.37,38 During the optimization, except for the two bottom layers of the slabs that remain fixed, all other atom positions are fully relaxed until the residual forces are less than 0.03 eVÅ−1. The convergence criterion of the energy is 10−5 eV. The first Brillouin zone is sampled with a Γ-centered K-point mesh. The adsorption energy, Ead, is defined as Ead = Etotal − EClFePc − Esub, where Etotal, EClFePc, and Esub denote the energy of ClFePc on the substrate, ClFePc in vacuum, and the substrate, respectively. To determine the dechlorination barrier and pathway of ClFePc, transition states are located using the climbing image nudged-elastic band (CI-NEB) method implemented in VASP through the VASP Transition State Tools (VTST).39,40 In NEB calculations, the convergence criterion for ionic steps is 0.05 eVÅ−1. Results and Discussion Figure 1a shows a STM image of a clean Au(111) surface, which exhibits a typical herringbone reconstruction. The ClFePc molecule features a cross-like configuration with a Cl atom protruding from the molecular π-plane, as illustrated in Figure 1b. ClFePc molecules are thermally evaporated onto the Au(111) surface at about room temperature (RT). At lower coverages, three distinct kinds of adsorption structures are observed (Figure 2a). The first structure, labeled as M1, exhibits a characteristic cross-like morphology similar to that of Pc-type molecules, with one of the diagonal symmetry axes deviating by 15° from the [ 11 2 ¯ ] direction of the Au(111) substrate, as marked by the red dashed arrow in Figure 2b. Notably, a bright spot is visible between the two lobes. The second structure, labeled as M2, also displays a typical cross-like morphology akin to that of Pc-type molecules (Figure 2c), with one of the diagonal symmetry axes (blue dashed arrows) extending along the [ 11 2 ¯ ] direction. Finally, the third structure, labeled as M3, exhibits four lobes with dramatically distinct contrast relative to the center (Figure 2d), in the same direction as M2. Therefore, the M1 molecules rotate by 15° with respect to both M2 and M3 molecules. Figure 1 | (a) STM image of the clean Au(111) surface with a herringbone reconstruction (1 V, 20 pA). (b) Molecular structure of ClFePc. Download figure Download PowerPoint The distinct morphologies of dipolar phthalocyanines observed in STM images are usually attributed to variations in the molecular adsorption behavior. The discrepancies in the self-assembly patterns of the three molecular configurations suggest that the interactions between the surface and the molecules vary significantly among them. To investigate the adsorption behavior and potential adsorption configurations, theoretical calculations are conducted. Specifically, simulations are performed for ClFePc with Cl-up and Cl-down adsorption configurations at four distinct surface adsorption sites: fcc, hcp, top, and bridge. Additionally, these simulations consider the scenarios where the diagonal symmetry axes of the two configurations are along the [ 11 2 ¯ ] direction and the direction rotated by 15° with respect to [ 11 2 ¯ ], respectively. By comparing the adsorption energies among these configurations, we identify the most stable adsorption configuration as the Cl-up configuration at the fcc site with one of the diagonal symmetry axes along [ 11 2 ¯ ] direction (Table 1). The adsorption energy of this configuration is −4.12 eV, which is close to the magnitude of the previously reported adsorption energy of ClAlPc on Au(111).41 Our calculations suggest that the Cl-up configurations are more stable than Cl-down, with energy differences ranging from 0.50 to 0.85 eV between them. These findings indicate that ClFePc prefers the Cl-up configuration on the Au(111) surface, as depicted in Figure 2g. Besides, the hcp and bridge configurations of Cl-up are relatively metastable. It is acceptable that one of the three observed STM topographies most likely corresponds to ClFePc in a Cl-up configuration. Table 1 | Adsorption Energy of Cl-Up and Cl-Down Configurations at Different Adsorption Sites and Two Adsorption Directions (0° and 15°) on Au(111). Two Adsorption Directions (Diagonal Symmetry Axes Along the [ 11 2 ¯ ] Direction and Rotated by 15° with Respect to [ 11 2 ¯ ]) are also Incorporated Adsorption Site Adsorption Energy (eV) Cl-Up Cl-Down 0° ( [ 11 2 ¯ ]) 15° 0° ( [ 11 2 ¯ ]) 15° fcc −4.12 −4.10 −3.62 −3.44 hcp −4.11 −4.06 −3.45 −3.46 Top −3.86 −3.99 −3.27 −3.40 Bridge −4.10 −3.98 −3.57 −3.55 Figure 2 | (a) Constant current STM images of ClFePc adsorbed on Au(111) after deposition at about RT (100 mV, 30 pA). These different molecular morphologies coexist and are specified by M1 (purple dashed cycle), M2 (orange dashed cycle), and M3 (green dashed cycle). (b–d) High-resolution STM images. (M1: 40 mV, 40 pA, 2 × 2 nm²; M2: 30 mV, 50 pA, 2 × 2 nm²; M3: 30 mV, 30 pA, 2 × 2 nm²). (e–g). Top and side views of the optimized structures corresponding to (b–d). Blue and red dashed arrows indicate the [112] direction of the substrate and the direction rotated by 15° with respect to the [112], respectively. Download figure Download PowerPoint Remarkably, the morphological characteristics of M1 are the most distinctive, and a similar structure has never been observed in the assembly investigations of analogous dipolar nonplanar molecules.13,14,17 We speculate that the distinctive bright spot observed between the two lobes of the M1 molecule is attributable to an individual Cl atom (Figure 2b). This speculation is based on the possible dissociation of the Cl–Fe bond in ClFePc during the deposition process at about RT. Moreover, as reported in previous publications, the Cl atom originating from the dechlorination reaction could remain on the surface, which is confirmed by the fuzzy STM images.17 To confirm this hypothesis, it is necessary to assess the possibility of the dissociation of the Cl–Fe bond. Based on the discussions above, the Cl-down configuration is considered unstable. When the Cl end of the molecule is downward and in contact with the Au(111) surface, the Cl–Fe bond may be activated by the Au(111) surface. To investigate the reaction pathway and energy involved in the dissociation of the Cl–Fe bond in the Cl-down configuration, CI-NEB calculations are employed. The initial state (IS) corresponds to the Cl-down configuration (Figure 3a). To obtain the final state (FS), we remove the chlorine atom from the molecule in the Cl-down configuration and reposition it proximate to and beneath the molecule. Subsequently, we get the dechlorinated structure labeled FePc-Cl after relaxing the system, in which the Cl atom is stabilized between two isoindole rings of the molecular fragment (FePc). Specifically, given the sizable adsorption energy of Cl atoms on Au(111),42 the Cl atom remains affixed to the substrate, maintaining residual interaction with FePc. Based on these two structures, the NEB calculations are performed. The pathway of the dechlorination is visually represented in Figure 3a. This is an exothermic process, with an activation energy of Ea = 0.60 eV and a reaction energy of Er = −0.82 eV, as shown in Figure 3b. The relatively low energy barrier and the negative reaction energy of the Cl migration process ensure the irreversible dissociation of the Cl-Fe bond in the Cl-down configuration at about RT. Notably, due to a significantly high energy barrier of 1.90 eV, the Cl atom cannot migrate to the upper position of FePc to form a Cl-up configuration ( Supporting Information Figure S1). In addition, considering the possibility of Cl–Fe bond dissociation in the Cl-up configuration, the simulated reaction pathway is illustrated in Figure 3c,d, with Ea of 1.49 eV. Since this reaction also requires a high activation energy, it is difficult to occur at RT. Figure 3 | (a) Reaction pathway and (b) calculated energies for the dissociation of the Cl–Fe bond in the Cl-down configuration. The molecular models presented correspond to the initial (IS), transition (TS), and final (FS) states of the reaction process. Ea and Er refer to the activation and reaction energies, respectively. The (c) reaction pathway and (d) calculated energies of the dechlorination reaction in the Cl-up configuration. Download figure Download PowerPoint The dissociation of the Cl–Fe bond on the Au(111) surface is consistent with the absence of Cl-down molecules on the surface. Moreover, once the Cl–Fe bond is broken, the Cl atom migrates near the center axis between the two isoindole rings, further suggesting that the small bright spot of M1 molecule observed experimentally is the Cl atom released after the dissociation of the Cl–Fe bond (Figure 2b). STM images have revealed that the diagonal symmetry axis of M1 deviates by 15° from the [ 11 2 ¯ ] orientation of Au(111). To determine the adsorption sites of M1, the total energies of FePc-Cl structures with various adsorption sites under this adsorption orientation are calculated. Our results indicate that the most stable configuration is achieved when the Fe atom is positioned at the bridge site. Consequently, M1 is identified as the FePc-Cl structure with Fe located at the bridge site, with one of its diagonal symmetry axes deviating by 15° from the [ 11 2 ¯ ] direction (Figure 2e). In addition, the Cl-up configuration is stable on the surface and resistant to activation. The direct interaction between the ligand Cl and the Au(111) surface is critical to Cl–Fe bond dissociation in the bidirectional adsorption of ClFePc on the surface. These findings highlight the remarkable catalytic activity of the Au(111) surface which facilitates the dechlorination of ClFePc molecules by effectively reducing the reaction barrier. To further study the spin characteristics of the molecules, dI/dV spectra are measured at the centers of M1-3 adsorption configurations. Concurrently, DFT calculations are employed to explore the corresponding geometric and electronic structures, providing a comprehensive picture of these systems. As shown in Figure 4, all molecules exhibit Kondo resonance features near EF.43,44 M1 (FePc-Cl) displays a broad peak (Figure 4a), similar to the spectra observed in previous studies for FePc adsorbed on the bridge site of the Au(111) surface.35 This broad peak is well reproduced by an asymmetric Fano peak (red curve in Figure 4a),45,46 suggesting that one channel screens the molecular spin. The Kondo temperatures (TK) of this spin channel can be determined through Fano fitting of the dI/dV spectra.47–50 This broad peak corresponds to a Kondo temperature of TK ≈ 58 K. The spin-polarized projected density of states (PDOS) for the 3dxz, 3dyz, and 3dz2 orbitals of Fe centers in this configuration is shown in Figure 4b. The majority and minority spin states exhibit unequal occupation, leading to a total spin magnetic moment of 1.96 μB, with the Fe ion of 2.12 μB. There are two unpaired electrons in FePc-Cl (S = 1), with one in the 3dz2 orbital and the other in the 3dπ (3dxz and 3dyz) orbitals. It is noted that the peaks of the 3dxz and 3dyz orbitals are separate. Taking into account the characteristics of the geometric structure, we deduce that the splitting of the 3dπ orbitals is caused by the bridge site adsorption.35 The adsorption of FePc-Cl at the bridge site reduces the symmetry around the Fe atom and breaks the degeneracy of the 3dπ orbitals, thereby freezing the orbital degrees of freedom. As a consequence, only the 3dz2 orbital is screened by the delocalized electron gas of the Au substrate, which corresponds to the SU(2) Kondo effect.35 Furthermore, the magnetic moment of ClFePc in vacuum is 3.00 μB, and that of Fe is 2.38 μB, corresponding to a spin state of 3/2. It is evident that the catalysis of dissociation reactions by the Au(111) surface results in the modulation of not only the geometric structure but also the spin states. Figure 4 | The dI/dV spectra obtained above the centers of the three adsorption configurations at 4.3 K, along with the corresponding PDOS for the 3dxz, 3dyz and 3dz2 orbitals of the Fe center, respectively. The black curves in the dI/dV spectra indicate the experimental data, while the red curves depict the fit using Fano functions, and the insets show the corresponding high-resolution STM images. (a) The dI/dV spectra for M1. (b) PDOS of FePc-Cl. (c) The dI/dV spectra for M2. (d) PDOS of FePc. (e) The dI/dV spectra for M3. (f) PDOS of ClFePc. Download figure Download PowerPoint For the M2 structure, a sharp antiresonance appears near zero bias voltage, accompanied by a broad peak-like background (Figure 4c). This spectral feature can be fitted by two Fano functions, suggesting that two channels screen the molecular spin and show different Kondo temperatures. The dip antiresonance reflects the low-T Kondo channel with TK ≈ 8 K, and the broad peak corresponds to the high-T Kondo channel with TK ≈ 103 K. This spectral signature is consistent with previous reports on FePc molecules adsorbed on the top site of Au(111).35,51 Furthermore, the molecular morphology of M2 resembles that of the top-site FePc molecule. Based on these observations, we confirm that M2 is indeed a FePc molecule adsorbed on the top site, as depicted in Figure 2f. The total magnetic moment of FePc is 1.92 μB, and the Fe ion is 2.06 μB, corresponding to a spin state of S = 1 (Figure 4d). In the fourfold symmetric configuration of M2, both the 3dz2 and 3dπ orbitals undergo screening, resulting in a spectrum composed of two Kondo resonances. It is worth noting that the Kondo temperature obtained here is slightly higher than previously reported values. This discrepancy can be attributed to a temperature-induced broadening of the Kondo resonance52 because the measured temperature is higher than that reported in the published work. It is conceivable that these separated FePc molecules may originate as residual products after the further migration of Cl atoms in FePc-Cl structures on the surface. A tip manipulation experiment conducted on M1 reveals that by applying a tip pulse of 2.0 V at its center, M1 can be switched to M2, accompanied by changes in the STS spectra ( Supporting Information Figure S2). This finding underscores the logical conclusion that FePc emerges as a product of the further migration of Cl. For M3, the measured dI/dV spectrum is fitted by a Fano dip, accompanied by a Gaussian-shaped background (Figure 4e).53,54 The Kondo temperature is determined to be TK ≈ 23 K. Remarkably, the spectral features of M3 exhibit minimal similarity to the Kondo signal of FePc, and its molecular morphology differs obviously from that of FePc. Through the analysis above, it can be confirmed that M3 is ClFePc in a stable Cl-up configuration (Figure 1g). The magnetic moment of ClFePc in the Cl-up configuration is 2.95 μB and of the Fe ion is 2.47 μB. The valence of Fe is approximately +3, and each Fe3+ owns three unpaired electrons (S = 3/2): one in the 3dz2 orbital and two in the 3dπ orbitals (dxz and dyz, each occupied by one electron, Figure 4f). The observed Kondo screening effect can be ascribed to the 3dz2 orbital channel because the hybridization of the 3dz2 orbital with the substrate is significantly stronger than other orbitals. This is due to its unique shape and orientation.53 Conclusion In summary, through STM and STS experiments and DFT calculations, we discovered that ClFePc molecules adsorb either in the Cl-up configuration or undergo dechlorination on the Au(111) surface at about RT. When adsorbed in the Cl-down configuration, the Cl–Fe bond in the molecule breaks. That is, it undergoes the dechlorination process which is catalyzed by the Au(111) surface, and the Cl atom migrates near the center axis between the two isoindole rings, forming the FePc-Cl structure. This reaction is energetically favorable, with an activation energy of 0.60 eV and a reaction energy of −0.82 eV as calculated. Through analyzing the characteristics of the observed Kondo resonances and the PDOS, the spin state of the Cl-up configuration is determined to be 3/2, which is consistent with that of ClFePc in vacuum. Once dechlorinated on the Au(111) surface, the spin state of the product FePc-Cl structure is turned into S = 1. Additionally, separated FePc molecules are also observed on the surface, which are residual products of FePc-Cl after further migration of Cl atoms. These results highlight the need for careful consideration of surface-catalyzed reactions in exploring such interfaces and provide enlightening clues for the modulation of magnetic properties in spintronics. Supporting Information Supporting Information is available and includes NEB calculations for the migration of the Cl atom and the tip manipulation experiment. Conflict of Interest The authors declare no competing interests. Funding Information This work is supported by the National Natural Science Foundation of China (grant nos. 22225202, 92356309, 22132007, 21991132, and 22172002). Acknowledgments DFT calculations are carried out on the TianHe-1A at National Supercomputer Center in Tianjin and supported by the High-Performance Computing Platform of Peking University. Experiments are supported by Peking Nanofab. References 1. 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