2D mesoporous atomic monolayers of phenyleneethynylene oligomers on pyrolytic graphite surfaces analyzed by scanning tunneling microscopy

Turlakov, Gleb; Arias, Eduardo; Moggio, Ivana; Rodríguez, Joelis; Rodríguez, Geraldina; Ziolo, Ronald F.; Scavia, Guido; Zappia, Stefania

doi:10.1016/j.apsusc.2020.145916

Cited by 2 publications

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“…We 11 and others 12 also previously reported that the supramolecular organization of phenyleneethynylenes depends strongly on the number of repetitive units and the termini or side chains. In particular, we demonstrated the effect of benzyl or carboxylic acid terminal groups in trimers and pentamers with a dodecanoxy lateral chain in the central phenyl group.…”

Section: Introductionmentioning

confidence: 64%

“…However, at least two supramolecular interactions could be considered (vide infra), as shown in Figure d. In this respect, we and others recently published that (benzyl) benzoate and carboxylic acid-terminated phenyleneethynylene macromolecules bearing dodecanoxy (or hexyloxy) side chains form stable 2D films on HOPG. , We found that for the (benzyl) benzoate-terminated oligomers, a staggered arrangement of molecules occurs endorsed by the π–π interaction between the benzyls. In contrast, for the carboxylic acid-terminated oligomers, a linear-type arrangement is promoted by the hydrogen bond created between the carboxylic acid groups.…”

Section: Resultsmentioning

confidence: 98%

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Photophysical and Electrochemical Properties of Push–Pull Oligo(ferrocenyl-phenyleneethynylene)s: Supramolecular Orders in Molecular Films

et al. 2022

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We report on the optoelectronic properties of a series of unsymmetrical π-conjugated phenyleneethynylene macromolecules bearing ferrocene (Fc) as the electron-donor group (D), (benzyl) benzoate (Bz) or benzoic acid (Ac) as the electron attractor group (A) and connected through 2,5-di(alcoxy) phenyleneethynylene(s) (nPE) with n = 1, 2, 3 as π-conjugated bridges. In the series, by increasing the distance between the electron-attracting and electron-donor groups, the push−pull effect decreases. The intramolecular charge transfer (D → π → A) was evaluated by static and dynamic spectroscopy, electrochemistry, and density functional theory (DFT) theoretical calculations. The longest oligomer Fc3PEBz formed the best optical quality films. A study at the atomic level by scanning tunneling microscopy (STM) revealed that the molecules self-assemble on highly ordered pyrolytic graphite (HOPG) in domains with a short-range order. Films are mesoporous and the molecules arrange in a lamellar-like pattern, with an edge-on conformation with respect to HOPG, where the conjugated backbones lie parallel to the surface. Two different assemblies were identified in the monoatomic film, which depends on the ferrocene−ferrocene or benzyl−benzyl interactions.

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Section: Introductionmentioning

confidence: 64%

Section: Resultsmentioning

confidence: 98%