Molecular <scp>Self‐Assembly</scp> of Phenylselenyl Chloride on a Au(111) Surface

Han, Myung-Soo; Seong, Sicheon; Han, Seulki; Lee, Nam Suk; Noh, Jaegeun

doi:10.1002/bkcs.12116

Cited by 6 publications

(7 citation statements)

References 43 publications

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“…Closely packed and highly ordered self-assembled monolayers (SAMs) can be prepared by the spontaneous adsorption on metals of organic molecules containing chemically active sulfur, selenium, carboxylic or alkyne anchoring groups [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. As a result, SAMs provide a very useful route for the fabrication of multifunctional molecular thin films that can be applied to various practical applications in the fields of biotechnology and nanotechnology [ 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

Thermally Driven Structural Order of Oligo(Ethylene Glycol)-Terminated Alkanethiol Monolayers on Au(111) Prepared by Vapor Deposition

Son

Kang²,

Seong³

et al. 2022

Molecules

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To probe the effects of deposition temperature on the formation and structural order of self-assembled monolayers (SAMs) on Au(111) prepared by vapor deposition of 2-(2-methoxyethoxy)ethanethiol (CH3O(CH2)2O(CH2)2SH, EG2) for 24 h, we examined the surface structure and electrochemical behavior of the resulting EG2 SAMs using scanning tunneling microscopy (STM) and cyclic voltammetry (CV). STM observations clearly revealed that EG2 SAMs vapor-deposited on Au(111) at 298 K were composed of a disordered phase on the entire Au surface, whereas those formed at 323 K showed improved structural order, showing a mixed phase of ordered and disordered phases. Moreover, at 348 K, uniform and highly ordered EG2 SAMs on Au(111) were formed with a (2 × 3√3) packing structure. CV measurements showed sharp reductive desorption (RD) peaks at −0.818, −0.861, and −0.880 V for EG2 SAM-modified Au electrodes formed at 298, 323, and 348 K, respectively. More negative potential shifts of RD peaks with increasing deposition temperature are attributed to an increase in van der Waals interactions between EG2 molecular backbones resulting from the improved structural quality of EG2 SAMs. Our results obtained herein provide new insights into the formation and thermally driven structural order of oligo(ethylene glycol)-terminated SAMs vapor-deposited on Au(111).

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Section: Introductionmentioning

confidence: 99%

Thermally Driven Structural Order of Oligo(Ethylene Glycol)-Terminated Alkanethiol Monolayers on Au(111) Prepared by Vapor Deposition

Son

Kang²,

Seong³

et al. 2022

Molecules

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“…The functionalization of solid surfaces with nanoscale precision can be achieved using self‐assembled monolayers (SAMs) formed by adsorption of various adsorbates 1–16 . Therefore, SAMs have been extensively used in nanoscience and nanotechnology such as molecular sensors, 17 bio‐interface, 1,18,19 nanopatterning, 1,20 and molecular electronics 2,21–23 .…”

Section: Introductionmentioning

confidence: 99%

“…The adsorption geometry and surface structure of SAMs can be tuned by deposition time and temperature, 1,3,4,11,13 deposition methods (solution or vapor deposition), 3,24 the thermal annealing process, 7,25 and preparation solvent 15,26,27 . The interface characteristics of metals can be easily modulated via the formation of SAMs with different headgroups on the metal surfaces 1,2,5,14,28 . Alternatively, n ‐alkanethiols are the most popular molecular system for studying their self‐assembly phenomena and their surface structures depending on the alkyl chain length 1,11,13,27,29 .…”

Section: Introductionmentioning

confidence: 99%

Steric Effects on the Formation of Self‐Assembled Monolayers of Alicyclic Thiol Derivatives on Au(111)

Seong

Kwon

Han

et al. 2021

Bulletin Korean Chem Soc

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To understand the steric effects on the formation of alicyclic thiolate self‐assembled monolayers on Au(111), the surface structures and reductive desorption behaviors of self‐assembled monolayers on Au(111) derived from cyclohexanethiol (CHT) and 1‐methylcyclohexanethiols (MCHT) were characterized using scanning tunneling microscopy (STM) and cyclic voltammetry. STM observations showed that the adsorption of CHT on Au(111) resulted in the formation of well‐organized monolayers with an unit cell of a = 14.5 ± 0.3 Å and b = 10.2 ± 0.3 Å, while the adsorption of MCHT with a methyl substituent bonded to the 1‐position of the cyclohexyl ring resulted in the formation of a disordered phase. The reductive desorption potentials for CHT and MCHT monolayers on Au electrodes were observed at −0.984 and −0.974 V, respectively. This difference in potentials can be attributed to the difference in lateral interactions, which depend on the structural order of monolayers.

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“…It is noteworthy that most securinega alkaloids lack a functional handle for biofunctional derivatizations, considering that altering the electrophilic unsaturated γ-butyrolactone moiety is not desirable because it may interact with the nucleophilic moiety of the target (Scheme 1 B). Under these circumstances, isolations of securinega alkaloids with a hydroxy group, such as 4α-hydroxyallosecurinine ( 4 ), 16 securingine F ( 5 ), 17 or secu’amamine A ( 6 ) 18 19 20 21 22 are notable. 4α-Hydroxyallosecurinine ( 4 ) and securingine F ( 5 ) are especially interesting entries, as their hydroxy group is located remotely from both the unsaturated γ-butyrolactone and the N1 moieties, two probable sites for biological activities of the natural product.…”

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confidence: 99%

Total Synthesis of 4α-Hydroxyallosecurinine and Securingine F, Securinega Alkaloids with a C4-Hydroxy Handle for Biofunctional Derivatizations

Park

Kim

Yang

et al. 2023

Synlett

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We describe the first total synthesis of C4-hydroxylated securinega alkaloids 4α-hydroxyallosecurinine and securingine F. The synthetic route features an Ellman’s light-mediated hydrogen atom transfer (HAT)-based epimerization reaction which effectively set the desired configuration at the C2 position. Simultaneous skeletal rearragement from neosecurinane to securinane frameworks and stereochemical reversal at the C4 site was achieved under Misunobu reaction conditions. The C4-hydroxyl group is envisioned to serve as a handle for potential biofunctional derivatizations.

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Molecular Self‐Assembly of Phenylselenyl Chloride on a Au(111) Surface

Abstract: Surface‐mediated reductive adsorption and self‐assembly of phenylselenyl chlorides on Au(111).

Cited by 6 publications

References 43 publications

Thermally Driven Structural Order of Oligo(Ethylene Glycol)-Terminated Alkanethiol Monolayers on Au(111) Prepared by Vapor Deposition

Thermally Driven Structural Order of Oligo(Ethylene Glycol)-Terminated Alkanethiol Monolayers on Au(111) Prepared by Vapor Deposition

Steric Effects on the Formation of Self‐Assembled Monolayers of Alicyclic Thiol Derivatives on Au(111)

Total Synthesis of 4α-Hydroxyallosecurinine and Securingine F, Securinega Alkaloids with a C4-Hydroxy Handle for Biofunctional Derivatizations

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