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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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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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