Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 405422
Title Self-Assembly of Organic Monolayers onto Hydrogen-Terminated Silicon: 1-Alkynes Are Better Than 1-Alkenes
Author(s) Scheres, L.M.W.; Giesbers, M.; Zuilhof, H.
Source Langmuir 26 (2010)13. - ISSN 0743-7463 - p. 10924 - 10929.
Department(s) Laboratory for Organic Chemistry
Publication type Refereed Article in a scientific journal
Publication year 2010
Keyword(s) covalently attached monolayers - metal-semiconductor diodes - extremely mild attachment - alkyl monolayers - si(111) surface - visible-light - molecular electronics - thermal-reactions - si - alkenes
Abstract Recently, a new method for the preparation of high-quality organic monolayers with 1-alkynes at room temperature in the dark (i.e., without any external activation) was reported. To pinpoint the precise origin of this self-assembly process and to compare the reactivity of 1-alkenes and 1-alkynes toward hydrogen-terminated Si(111) [H-Si(111)], we followed the gradual formation of both monolayers at room temperature by static water contact angle measurements. Subsequently, attenuated total reflection infrared spectroscopy (ATR-IR) and X-ray photoelectron spectroscopy (XPS) were used to obtain detailed information about the structure and quality of the resulting monolayers. Our data clearly demonstrate that 1-alkynes are considerably more reactive toward H-Si(111) than 1-alkenes. 1-Alkynes are able to self-assemble into densely packed hydrophobic monolayers without any external activation (i.e., at room temperature under ambient light and even in the dark) whereas for 1-alkenes under the same conditions hardly any reactivity toward H-Si(111) was observed. The self-assembly of 1-alkynes on H-Si(111) at room temperature is explained by three factors: the higher nucleophilicity of 1-alkynes, which results in a facile attack at the electron-hole pairs at the H-Si surface and easy Si-C bond formation, the stabilization of the ß radical by delocalization over the double bond, and the lower-energy barrier encountered for H abstractions
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