Monomolecular covalent honeycomb nanosheets produced by surface-mediated polycondensation between 1,3,5-triamino benzene and benzene-1,3,5-tricarbox aldehyde on Au(111)

Kunitake, Masashi; Tanoue, Ryota; Higuchi, Rintaro; Haraguchi, Ryusei; Uemura, Shinobu; Kimizuka, Nobuo; Stieg, Adam Z.; Gimzewski, James K.

doi:10.1039/d0na00180e

Cited by 5 publications

(3 citation statements)

References 52 publications

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“…A dotted line is drawn in Figure c to indicate that DPDTTP admolecules were adsorbed on the ridges of the reconstructed pattern. This kind of variation in STM imaging has been reported with iodine and organic molecules adsorbed on Au(111) electrodes. − …”

Section: Resultssupporting

confidence: 56%

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: Resultssupporting

confidence: 56%

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 particular, the structure of the metal complex formed at the solid-liquid interface and the adsorption of the metal complex in the ionic liquid were highly evaluated by researchers in this field around the world. [48][49][50][51][52][53]…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Recent Activities for Relaunch Process of Electrochemistry to Gold Open Access Journal and Introduction of Award Winners in 2023

MIZUHATA,

UEDA

2023

Electrochemistry

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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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Monomolecular covalent honeycomb nanosheets produced by surface-mediated polycondensation between 1,3,5-triamino benzene and benzene-1,3,5-tricarbox aldehyde on Au(111)

Abstract: A large defect-free and homogeneous honeycomb π-conjugated nanosheet consisted of small aromatic building blocks at the solution/solid interface.

Cited by 5 publications

References 52 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

Recent Activities for Relaunch Process of Electrochemistry to Gold Open Access Journal and Introduction of Award Winners in 2023

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

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