Scanning Tunneling Microscopy Investigation of Copper Phthalocyanine and Truxenone Derivative Binary Superstructures on Graphite

Liu, Jia; Wang, Dong; Wang, Jieyu; Pei, Jian; Li, Wan

doi:10.1002/asia.201000628

Cited by 5 publications

(3 citation statements)

References 56 publications

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“…In other words, the weak interaction between CuPc separators and TBU lobes is compensated by desolvation energy of CuPc at the solid/liquid interface. A similar solvent effect to modulate the self-assembly has been observed in other systems. − By increasing the concentration of TCDB in the solution phase, and thus the coverage of it on the surface, the lobes grow bigger and form hierarchical structures with higher generations. At high coverage and suitable molar ratio of TCDB and TrO23, Flower 0 is preferred since the center-sitting TCDB provides extra hydrogen bonding to stabilize the structure.…”

Section: Resultsmentioning

confidence: 54%

Chiral Hierarchical Molecular Nanostructures on Two-Dimensional Surface by Controllable Trinary Self-Assembly

et al. 2011

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The bottom-up fabrication of surface hierarchical nanostructures is of great importance for the development of molecular nanostructures for chiral molecular recognition and enantioselective catalysis. Herein, we report the construction of a series of 2D chiral hierarchical structures by trinary molecular self-assembly with copper phthalocyanine (CuPc), 2,3,7,8,12,13-hexahexyloxy-truxenone (TrO23), and 1,3,5-tris(10-carboxydecyloxy) benzene (TCDB). A series of flower-like chiral hierarchical molecular architectures with increased generations are formed, and the details of these structures are investigated by high resolution scanning tunneling microscopy (STM). The flower-like hierarchical molecular architectures could be described by a unified configuration in which the lobe of each architecture is composed of a different number of triangular shape building units (TBUs). The off-axis edge-to-edge packing of TBUs confers the organizational chirality of the hierarchical assemblies. On the other hand, the TBUs can tile the surface in a vertex-sharing configuration, resulting in the expansion of chiral unit cells, which thereby further modulate the periodicity of chiral voids in the multilevel hierarchical assemblies. The formation of desired hierarchical structures could be controlled through tuning the molar ratio of each component in liquid phase. The results are significant for the design and fabrication of multicomponent chiral hierarchical molecular nanostructures.

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Section: Resultsmentioning

confidence: 54%

Chiral Hierarchical Molecular Nanostructures on Two-Dimensional Surface by Controllable Trinary Self-Assembly

et al. 2011

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“…Although the electrochemical deposition of [CoTmtppa] 4+ onto various electrode surfaces was previously studied in detail, ,, nothing is known about the spontaneous adsorption onto a conducting substrate. Undoubtedly, it will have an apparent advantage against electrochemical as well as vacuum deposition, , because these require an additional energy supply, while still preserving the homogeneity of spontaneously formed layers. , As graphite/graphene is nowadays the electronic material of choice in the above-mentioned applications, we focused on the spontaneous adsorption of [CoTmtppa] 4+ on HOPG (whereas a graphene C 150 -cluster was used as a theoretical model for the HOPG basal plane). EPR spectroscopy is a suitable technique for surface analysis, because it can provide direct qualitative and quantitative evidence of the unpaired electron (spin) distribution on a surface, which cannot be acquired by common surface methods.…”

Section: Introductionmentioning

confidence: 99%

Spontaneous Adsorption of a Co-Phthalocyanine Ionic Derivative on HOPG. An In Situ EPR Study

et al. 2014

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The spontaneous adsorption of [N,N′,N″,N′″tetramethyltetra-3,4-pyridino-porphyrazino-Co(II)] ([CoTmtppa] 4+ ) from an aqueous solution onto highly ordered pyrolytic graphite (HOPG) was followed by in situ electron paramagnetic resonance (EPR). The solution of [CoTmtppa] 4+ (CH 3 SO 4 ) 4− exhibits no EPR signal in the temperature range from 120 to 293 K. At room temperature, on the other hand, the EPR spectra of both spontaneously adsorbed and powdered [CoTmtppa] 4+ were unambiguously identified by the spectral simulations and quantum chemical calculations. The results indicated different geometries for the powdered and adsorbed samples. The time evolution of the EPR spectrum of [CoTmtppa] 4+ and that of HOPG during the adsorption made it possible to obtain a kinetic picture of the process. Finally, the structure and the redox stability of the magnetically active [CoTmtppa] 4+ molecular film on HOPG was studied by atomic force microscopy (AFM), X-ray photoelectron spectroscopy (XPS), UV−vis backscattering spectroscopy, and cyclic voltammetry. Our findings reveal that EPR is simultaneously capable of following the structural changes of ionic phthalocyanine as well as the spin state of the conducting electrons (CEs) of HOPG, whereas the spin state of the CEs does not change upon adsorption.

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“…23 Mixing 2,3,7,8,12,13hexahexyloxy-truxenone (TrO23) with copper phthalocyanine (CuPc) or 1,3,5-tris(R-carboxydecyloxy)benzene (TRCDB, R = different alkyl chain), TrO23 assembled into molecular lines or networks depending on types and concentrations of other components. 24,25 Further study indicated that the chirality in the basic structure motif formed with numbers of T10CDB (TRCDB, R = 10), TrO23 and CuPc molecules was kept and amplified in following hierarchical structures. 26 For cyanobenzyl modified truxene, only those adsorbing on surface kinks and edges are stable enough to be observed with non-contact atomic force microscopy due to high diffusion energy barriers at those positions.…”

Section: Introductionmentioning

confidence: 99%

Hydrogen bonding network of truxenone on a graphite surface studied with scanning tunneling microscopy and theoretical computation

Yang

Tao

Chen

et al. 2013

Phys. Chem. Chem. Phys.

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The self-assembly of truxenone on highly oriented pyrolytical graphite (HOPG) was investigated with scanning tunneling microscopy (STM) and density functional theory (DFT) calculations. Truxenone assembled into a dense hexagonal adlayer with large and near-perfect domains on the graphite surface. Two types of topography image of truxenone were observed in experiments. DFT modeling indicates the center-hole image represents the contour of the lowest unoccupied molecular orbital (LUMO) of truxenone while the propeller-like image is more complicated and can't be assigned simply to an individual molecular orbital. Truxenone trimer was proposed as the basic unit of the adlayer through analysis of STM images and molecular structure. The optimized structure of the truxenone trimer by DFT calculation revealed that the hydrogen bonding network exists in the adlayer, which is responsible for the excellent stability and perfect domains of the whole assembly. In addition, the preferred adsorption site of truxenone on graphite was determined on the basis of DFT calculations and STM images. The results are of significance in supramolecular engineering by self-assembly and device fabrication based on truxenone and its derivatives.

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Scanning Tunneling Microscopy Investigation of Copper Phthalocyanine and Truxenone Derivative Binary Superstructures on Graphite

Cited by 5 publications

References 56 publications

Chiral Hierarchical Molecular Nanostructures on Two-Dimensional Surface by Controllable Trinary Self-Assembly

Chiral Hierarchical Molecular Nanostructures on Two-Dimensional Surface by Controllable Trinary Self-Assembly

Spontaneous Adsorption of a Co-Phthalocyanine Ionic Derivative on HOPG. An In Situ EPR Study

Hydrogen bonding network of truxenone on a graphite surface studied with scanning tunneling microscopy and theoretical computation

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