Self-assembly of organic monolayers onto hydrogen-terminated silicon : 1-alkynes are better than 1-alkenes

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 tow...

Ausführliche Beschreibung

Bibliographische Detailangaben
Veröffentlicht in:Langmuir : the ACS journal of surfaces and colloids. - 1992. - 26(2010), 13 vom: 06. Juli, Seite 10924-9
1. Verfasser: Scheres, Luc (VerfasserIn)
Weitere Verfasser: Giesbers, Marcel, Zuilhof, Han
Format: Online-Aufsatz
Sprache:English
Veröffentlicht: 2010
Zugriff auf das übergeordnete Werk:Langmuir : the ACS journal of surfaces and colloids
Schlagworte:Journal Article
LEADER 01000naa a22002652 4500
001 NLM19840834X
003 DE-627
005 20231223212643.0
007 cr uuu---uuuuu
008 231223s2010 xx |||||o 00| ||eng c
024 7 |a 10.1021/la100858q  |2 doi 
028 5 2 |a pubmed24n0661.xml 
035 |a (DE-627)NLM19840834X 
035 |a (NLM)20504006 
040 |a DE-627  |b ger  |c DE-627  |e rakwb 
041 |a eng 
100 1 |a Scheres, Luc  |e verfasserin  |4 aut 
245 1 0 |a Self-assembly of organic monolayers onto hydrogen-terminated silicon  |b 1-alkynes are better than 1-alkenes 
264 1 |c 2010 
336 |a Text  |b txt  |2 rdacontent 
337 |a ƒaComputermedien  |b c  |2 rdamedia 
338 |a ƒa Online-Ressource  |b cr  |2 rdacarrier 
500 |a Date Completed 30.09.2010 
500 |a Date Revised 23.12.2020 
500 |a published: Print 
500 |a Citation Status PubMed-not-MEDLINE 
520 |a 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 beta radical by delocalization over the double bond, and the lower-energy barrier encountered for H abstractions 
650 4 |a Journal Article 
700 1 |a Giesbers, Marcel  |e verfasserin  |4 aut 
700 1 |a Zuilhof, Han  |e verfasserin  |4 aut 
773 0 8 |i Enthalten in  |t Langmuir : the ACS journal of surfaces and colloids  |d 1992  |g 26(2010), 13 vom: 06. Juli, Seite 10924-9  |w (DE-627)NLM098181009  |x 1520-5827  |7 nnns 
773 1 8 |g volume:26  |g year:2010  |g number:13  |g day:06  |g month:07  |g pages:10924-9 
856 4 0 |u http://dx.doi.org/10.1021/la100858q  |3 Volltext 
912 |a GBV_USEFLAG_A 
912 |a SYSFLAG_A 
912 |a GBV_NLM 
912 |a GBV_ILN_22 
912 |a GBV_ILN_350 
912 |a GBV_ILN_721 
951 |a AR 
952 |d 26  |j 2010  |e 13  |b 06  |c 07  |h 10924-9