In situ scanning tunneling microscopy characterization of thienothiophene-based semiconducting organic molecules adsorbed on a Au(111) electrode

Luo, Shu Rong; Chen, Sih Zih; Hsu, Ya Hua; Yau, Shueh Lin; Lin, Yu Jou; Huang, Peng; Chen, Ming Chou

doi:10.1016/j.susc.2013.05.013

Cited by 5 publications

(7 citation statements)

References 38 publications

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“…These conditions likely increased the surface coverage of DPDTTP to values too high to allow an ordered arrangement. These conditions appear to be optimal for a number of organic molecules adsorbed on the Au(111) electrode. , …”

Section: Resultsmentioning

confidence: 99%

“…These conditions appear to be optimal for a number of organic molecules adsorbed on the Au(111) electrode. 26,40 Shifting the potential negatively resulted in no change of the ordered DPDTTP adlayer until −0.1 V, where the ordered DPDTTP patches markedly shrank, as seen in Figure 3b. This result shows that the DPDTTP admolecule was desorbed at potentials negative of −0.1 V, which reflects the strength of the van der Waals interaction between DPDTTP and Au.…”

Section: Single-crystalmentioning

confidence: 93%

“…We also explored the susceptibility to electrochemical oxidation and reduction of thiophene and pyrazine-based DPDTTP molecules at the Au electrode. A few in situ STM studies have addressed the adsorption of thiophene molecules at electrified interfaces. ,− In one case, it is shown that potential modulation could change the orientation of the thiophene admolecule on Au(111) and Au(100) electrodes . Generally speaking, the role of ion adsorption at the electrified interface has largely been overlooked.…”

Section: Introductionmentioning

confidence: 99%

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Potential-Controlled Organization of 2,3-Diphenyl-5,7-di(thiophen-2-yl)thieno[3,4-b]pyrazine Adsorbed on Au(111) and Au(100) Electrodes

et al. 2022

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The 2,3-diphenyl-5,7-di(thiophen-2-yl)thieno[3,4-b]pyrazine (DPDTTP) molecule is an organic molecule that is often used to produce photovoltaics and light-emitting diodes. The orientation of an organic semiconductor molecule at the metallic interface can affect the charge injection efficiency. The current study employed in situ scanning tunneling microscopy (STM) to examine the adsorption orientation of DPDTTP molecules on an ordered Au(111) electrode in 0.1 M HClO4, H2SO4, and HCl. DPDTTP molecules were found to irreversibly adsorbed onto the Au electrode from a 10 μM dosing solution. Molecular-resolution STM images were obtained to reveal their spatial structure as functions of the chemical identity of the supporting electrolyte, the atomic structure of the Au(111) substrate, and the potential control. Only the reconstructed Au(111) electrode afforded ordered DPDTTP adlattices between −0.1 and 0.4 V (vs Ag/AgCl) in HClO4 and H2SO4, and the DPDTTP adlayer became more compact with more positive potential. In 0.1 M HCl, pre-adsorbed DPDTTP molecules on the Au(111) electrode were displaced by chloride anions at E > 0.2 V, as evidenced by a well-ordered hexagonal array with a nearest-neighbor spacing of 3.8 ± 0.1 Å. The DPDTTP admolecule desorbed at E < −0.1 V in all acids. High-quality STM images were acquired to reveal two kinds of molecular conformations, as also found in the bulk single crystal of DPDTTP. The prominent role of the reconstructed structure in guiding the formation of ordered DPDTTP structures was substantiated by examining DPDTTP adsorbed on the Au(100) electrode in HClO4.

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Section: Resultsmentioning

confidence: 99%

Section: Single-crystalmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

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Potential-Controlled Organization of 2,3-Diphenyl-5,7-di(thiophen-2-yl)thieno[3,4-b]pyrazine Adsorbed on Au(111) and Au(100) Electrodes

et al. 2022

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“…In addition to the intrinsic characteristics of FHC molecules, their spatial structures in fabricated films can influence the mobility of charge carriers and the photo efficiencies of solar cells. In situ scanning tunneling microscopy (STM) is a powerful tool to study molecular adsorption on a metal substrate. − FHC molecules including 3,4-ethylenedioxythiophene, , terthiophene (TT), thienothiophene (DTT), 2,3-diphenyl-5,7-di(thiophen-2-yl)thieno[3,4- b ]pyrazine (DPDTTP), 3′,4′-bis(hexylthio)-2,2′:5′,2″-terthiophene (DTDST) have been examined by STM …”

Section: Introductionmentioning

confidence: 99%

Scanning Tunneling Microscopy Examination of Molecules with Fused Thiophene and Pyrrole Groups Adsorbed on the Electrified Au(111) Interface

Balasaravanan,

Hsieh,

Jhou

et al. 2024

J. Phys. Chem. C

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Molecules with a fused pyrrole and thiophene backbone can be harnessed into organic semiconductors and optoelectronics devices. Closely related to these applications is contact with a frequently used gold electrode. This organic/metal interface has been examined with scanning tunneling microscopy (STM) at the molecular level, revealing the adsorption orientation and spatial structure of the Au(111) electrode. The current study focused on the adsorption of 1,4-bis(4H-dithieno[3,2-b:2′,3′-d]pyrrol-4-yl)benzene (BDTP) on an ordered Au(111) electrode. The BDTP adlayer was adsorbed onto a Au crystal by immersion in 0.01 mM BDTP/benzene dosing solution for 2 min after the Au electrode was pretreated with the annealing-and-quenching process. The STM experiment was performed in 0.1 M HClO 4 or H 2 SO 4 under potential control. The cyclic voltammetric results indicate that the BDTP adlayer was stable between −0.2 and 0.7 V (versus Ag/AgCl) in both acids before desorption and oxidation commenced at negative and positive potentials. High-quality STM imaging was achieved to provide insights into the interactions between BDTP admolecules and with the Au support. The van der Waals interaction between BDTP and Au(111) was strong enough to partially lift the Au(111)-(√3 × 22) reconstructed phase. The threedimensional adsorption configuration of the BDTP admolecule on the Au(111) electrode is inferred from the corrugated features in the STM image. Potential control affected the interfacial interactions, the coadsorption of anions, and finally the spatial molecular arrangement on the Au electrode.

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“…Scanning tunneling microscopy, which exploits the p-type (hole) or n-type (electron) conductive properties of 2D assemblies of molecular semiconductors, is very well suited for this type of investigation and was frequently used for elucidating molecular packing and electrical properties of thiophene oligomers, for example. − Recently, these investigations have been expanded to more complex thiophene-based heteromacromolecules, like: thiophene-fluorene, thiophene-phenylene, thienothiophene, , and oxadiazole-thiophene derivatives, with the aim to determine the influence of different parts of their molecular heterostructure on the supramolecular organization of these adsorbates in the monomolecular layer.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembly Properties of Semiconducting Donor–Acceptor–Donor Bithienyl Derivatives of Tetrazine and Thiadiazole—Effect of the Electron Accepting Central Ring

et al. 2013

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Scanning tunneling microscopy was used to study the effect of the electron-accepting unit and the alkyl substituent's position on the type and extent of 2D supramolecular organization of penta-ring donor-acceptor-donor (DAD) semiconductors, consisting of either tetrazine or thiadiazole central acceptor ring symmetrically attached to two bithienyl groups. Microscopic observations of monomolecular layers on HOPG of four alkyl derivatives of the studied adsorbates indicate significant differences in their 2D organizations. Ordered monolayers of thiadiazole derivatives are relatively loose and, independent of the position of alkyl substituents, characterized by large intermolecular separation of acceptor units in the adjacent molecules located in the face-to-face configuration. The 2D supramolecular architecture in both derivatives of thiadiazole is very sensitive to the alkyl substituent's position. Significantly different behavior is observed for derivatives of tetrazine (which is a stronger electron acceptor). Stronger intermolecular DA interactions in these adsorbates generate an intermolecular shift in the monolayer, which is a dominant factor determining the 2D structural organization. As a consequence of this molecular arrangement, tetrazine groups (A segments) face thiophene rings (D segments) of the neighboring molecules. Monolayers of tetrazine derivatives are therefore much more densely packed and characterized by similar π-stacking of molecules independently of the position of alkyl substituents. Moreover, a comparative study of 3D supramolecular organization, deduced from the X-ray diffraction patterns, is also presented clearly confirming the polymorphism of the studied adsorbates.

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In situ scanning tunneling microscopy characterization of thienothiophene-based semiconducting organic molecules adsorbed on a Au(111) electrode

Cited by 5 publications

References 38 publications

Potential-Controlled Organization of 2,3-Diphenyl-5,7-di(thiophen-2-yl)thieno[3,4-b]pyrazine Adsorbed on Au(111) and Au(100) Electrodes

Potential-Controlled Organization of 2,3-Diphenyl-5,7-di(thiophen-2-yl)thieno[3,4-b]pyrazine Adsorbed on Au(111) and Au(100) Electrodes

Scanning Tunneling Microscopy Examination of Molecules with Fused Thiophene and Pyrrole Groups Adsorbed on the Electrified Au(111) Interface

Self-Assembly Properties of Semiconducting Donor–Acceptor–Donor Bithienyl Derivatives of Tetrazine and Thiadiazole—Effect of the Electron Accepting Central Ring

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