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Odd-even effects in the structure and properties of aryl-substituted aliphatic self-assembled monolayers

Nano Research 2024年第5期17卷 4231-4243页

作者： Piotr Cyganik Andreas Terfort michael zharnikov Jagiellonian University Faculty of PhysicsAstronomy and Applied Computer ScienceSmoluchowski Institute of PhysicsŁojasiewicza 1130-348 KrakówPoland Institut für Anorganische und Analytische Chemie Universität FrankfurtMax-von-Laue-Straße 760438 FrankfurtGermany Applied Physical Chemistry Heidelberg UniversityIm Neuenheimer Feld 25369120 HeidelbergGermany

Self-assembled monolayers(SAMs)represent an important tool in context of nanofabrication and molecular engineering of surfaces and *** properties of functional SAMs depend not only on the character of the tail groups at the SAM-ambient interface,but are also largely defined by their *** its turn,the latter parameter results from a complex interplay of the structural forces and a variety of other factors,including so called odd-even effects,*** of the SAM structure and properties on the parity of the number(odd or even)of individual building blocks in the backbone of the SAM *** most impressive manifestation of the odd-even effects is the structure of aryl-substituted alkanethiolate SAMs on Au(111)and Ag(111),in which,in spite of the fact that the intermolecular interaction is mostly determined by the aryl part of the monolayers,one observes a pronounced dependence of molecular inclination and,consequently,the packing density of the SAM-forming molecules on the parity of number of methylene units in the alkyl *** we review the properties of the above systems as well as address fundamental reasons behind the odd-even effects,including the existence of a so-called bending potential,which is frequently disregarded in analysis of the structure-building *** generality of the odd-even effects in SAMs is additionally supported by the recent data for SAMs on GaAs,scanning tunneling microscopy data for SAMs on Ag(111),and the data for the monolayers with selenolate and carboxyl anchoring groups on Au(111)and Ag(111).The implications of these effects in terms of the control over the packing density and orientation of the tail groups at the SAM-ambient interface,structural perfection,polymorphism,temperature-driven phase transitions,and SAM stability toward such factors as ionizing radiation,exchange reaction,and electrochemical desorption are *** implications place the odd-even effects as an important tool

关键词： self-assembled monolayers molecular films surface and interface engineering odd-even-effects

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Aromatic self-assembled monolayers with pentafluoro-λ^(6)-sulfanyl(−SF_(5))termination:Molecular organization and charge transport properties

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Nano Research 2023年第5期16卷 7991-8002页

作者： Yangbiao Liu Marc Zeplichal Sonja Katzbach Adrian Wiesner Saunak Das reas Terfort michael zharnikov Angewandte Physikalische Chemie Universität HeidelbergIm Neuenheimer Feld 253D-69120 HeidelbergGermany Institut für Anorganische und Analytische Chemie Johann Wolfgang Goethe Universität FrankfurtMax-von-Laue-Straße 7D-60438 Frankfurt am MainGermany

A series of molecules with oligophenylene backbone,thiolate anchoring group,pentafluoro-λ^(6)-sulfanyl(−SF_(5))tail group was synthesized and used as precursors to form self-assembled monolayers(SAMs)on Au(111)*** resulting SAMs feature dense molecular packing,upright molecular orientation,chemically homogeneous SAM-ambient interface,comprised entirely of the−SF_(5)*** SAMs exhibit exceptional wetting and electrostatic properties,showing advancing water contact angles up to 103°and work function values up to 5.96 eV—probably the highest values reported for any aromatic monolayers on *** also feature a comparably low value of the tunnelling decay coefficient(0.38±0.07Å^(−1)),typical of oligophenylene backbone,which is not affected by the introduction of the−SF_(5)*** latter also hardly affects the current densities at a specific bias compared to analogous monolayers with other electronegative tail *** superior electrostatic and good charge transport properties of the designed,SF_(5)-terminated SAMs make them potentially useful for interface engineering in organic electronics and photovoltaics.

关键词： backbone charge electrostatic

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Lateral dipole moments induced by all-cis-pentafluorocyclohexyl groups cause unanticipated effects in self-assembled monolayers

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Nano Research 2023年第8期16卷 11030-11041页

作者： Christian Fischer Saunak Das Qingzhi Zhang Yangbiao Liu Lothar Weinhardt David O’Hagan michael zharnikov Andreas Terfort Institute of Inorganic and Analytical Chemistry Goethe University FrankfurtMax-von-Laue-Straße 760438 Frankfurt am MainGermany Applied Physical Chemistry Heidelberg UniversityIm Neuenheimer Feld 25369120 HeidelbergGermany School of Chemistry University of St AndrewsNorth HaughSt AndrewsFifeKY169STUK Institute for Photon Science and Synchrotron Radiation Karlsruhe Institute of Technology(KIT)Hermann-v.-Helmholtz-Platz 176344 Eggenstein-LeopoldshafenGermany Institute for Chemical Technology and Polymer Chemistry(ITCP) Karlsruhe Institute of Technology(KIT)Engesserstr.18/2076128 KarlsruheGermany Department of Chemistry and Biochemistry University of NevadaLas Vegas(UNLV)4505 Maryland ParkwayLas VegasNV 89154-4003USA

All-cis-hexafluoro-and all-cis-pentafluoro-cyclohexane(PFCH)derivatives are new kinds of materials,the structures and properties of which are dominated by the highly dipolar Janus-face ***,we report on the effects of integrating the PFCH groups into self-assembled monolayers(SAMs)of alkanethiolates on Au(111).Monolayers with an odd(eleven)and even(twelve)number of methylene groups were characterized in detail by several complementary experimental tools,supported by theoretical ***,all the data show a high similarity of both kinds of monolayers,nearly lacking the typically observed odd-even *** new monolayers have a packing density about 1/3 lower than that of non-substituted alkanethiolate monolayers,caused by the bulkiness of the PFCH *** orientations of the PFCH groups and the alkyl chains could be determined independently,suggesting a conformation similar to the one found in the solid state structure of an analogous *** in the SAMs the PFCH groups are slightly tilted away from the surface normal with the axial fluorine atoms pointing downwards,most of the dipole moments of the group remain oriented parallel to the surface,which is a unique feature for a SAM *** consequences are much lower water contact angles compared to other partly fluorinated SAMs as well as rather moderate work function *** interaction between the terminal PFCH moieties results in an enhanced stability of the PFCH-decorated SAMs toward exchange reaction with potential molecular substituents in spite of the lower packing density of these films.

关键词： odd-even-effects work function self-assembled monolayer(SAM) kinetic stability infrared-reflection absorption spectroscopy X-ray photoelectron spectroscopy

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The 3,4-dimethoxybenzyl group as solubilizing protective group for the in situ deprotection/deposition of extended aromatic thiolate monolayers

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Nano Research 2023年第1期16卷 1695-1702页

作者： Adrian Wiesner Sonja Katzbach Dariusz Bebej Martina Dettenhöfer michael zharnikov Andreas Terfort Institut für Anorganische und Analytische Chemie Johann Wolfgang Goethe Universität FrankfurtMax-von-Laue-Straße 7Frankfurt am Main D-60438Germany Angewandte Physikalische Chemie Universität HeidelbergIm Neuenheimer Feld 253Heidelberg D-69120Germany

While self-assembled monolayers(SAMs)of aromatic thiolates are frequently used in a wide range of applications,their formation is often hampered by the low solubilities of their *** we introduce the 3,4-dimethoxybenzyl group as a protective group for the thiol moiety,which increases the solubility and stability of the precursor,but becomes cleaved off during monolayer formation,especially at elevated temperature(60°C)and in presence of protons(trifluoroacetic acid).For a series of substituted terphenylthiols as model systems,it could be demonstrated by using ellipsometry,infrared-reflection absorption spectroscopy,and scanning-tunneling microscopy that the resulting SAMs have the same structure and quality as the ones obtained from the respective unprotected *** protective group has the additional advantage to be stable under Pdcatalyzed C–C bond formation reaction conditions,facilitating the syntheses of the respective precursors.

关键词： self-assembled monolayers protective group solubility scanning-tunneling microscopy infrared-reflection absorption spectroscopy

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