Grafting organic n-semiconductors to surfaces: (perfluoro-p-terphenyl-4-yl)alkanethiols
Perfluoroterphenyl, an organic n-semiconductor, has been derivatized by short ω-mercaptoalkyl chains to permit the formation of self-assembled monolayers on semiconductor and coinage metal substrates. Because the perfluoroaryl rings are prone to nucleophilic attack, strategies for the introduction o...
Saved in:
| Main Authors: | , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
April 14, 2010
|
| In: |
European journal of organic chemistry
Year: 2010, Issue: 16, Pages: 3041-3048 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.201000151 |
| Online Access: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/ejoc.201000151 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201000151 
|
| Author Notes: | Björn Schüpbach, Michael Bolte, Michael Zharnikov, and Andreas Terfort |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1851558314 | ||
| 003 | DE-627 | ||
| 005 | 20230710124537.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 230704s2010 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1002/ejoc.201000151 |2 doi | |
| 035 | |a (DE-627)1851558314 | ||
| 035 | |a (DE-599)KXP1851558314 | ||
| 035 | |a (OCoLC)1389793695 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 30 |2 sdnb | ||
| 100 | 1 | |a Schüpbach, Björn |d 1979- |e VerfasserIn |0 (DE-588)1019871474 |0 (DE-627)691042985 |0 (DE-576)359024106 |4 aut | |
| 245 | 1 | 0 | |a Grafting organic n-semiconductors to surfaces |b (perfluoro-p-terphenyl-4-yl)alkanethiols |c Björn Schüpbach, Michael Bolte, Michael Zharnikov, and Andreas Terfort |
| 264 | 1 | |c April 14, 2010 | |
| 300 | |a 8 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Gesehen am 04.07.2023 | ||
| 520 | |a Perfluoroterphenyl, an organic n-semiconductor, has been derivatized by short ω-mercaptoalkyl chains to permit the formation of self-assembled monolayers on semiconductor and coinage metal substrates. Because the perfluoroaryl rings are prone to nucleophilic attack, strategies for the introduction of the side chains had to be developed that avoid the use of any nucleophiles. Keeping this in mind, the respective derivatives with one, two, and three methylene groups in the alkyl linker could be obtained in good yields. The crystal structure of one of the intermediates, (perfluoroterphenyl-4-yl)methanol, exhibits a parallel arrangement of the molecules as well as a helical structure of the perfluoroterphenyl part, which is in contrast to the structure found for most nonfluorinated terphenyl derivatives. Using Au(111) as a test substrate, it could be demonstrated that all three thiols form dense monolayers with a pronounced odd-even effect governed by the parity of the number of methylene groups in the alkyl chain. | ||
| 650 | 4 | |a Aromatic substitution | |
| 650 | 4 | |a Helical structures | |
| 650 | 4 | |a Monolayers | |
| 650 | 4 | |a Nucleophilic substitution | |
| 650 | 4 | |a Perfluoroarene | |
| 650 | 4 | |a Self-assembly | |
| 700 | 1 | |a Bolte, Michael |e VerfasserIn |4 aut | |
| 700 | 1 | |a Zharnikov, Michael |e VerfasserIn |0 (DE-588)1118537629 |0 (DE-627)872019810 |0 (DE-576)479525889 |4 aut | |
| 700 | 1 | |a Terfort, Andreas |e VerfasserIn |0 (DE-588)172812232 |0 (DE-627)697742482 |0 (DE-576)133668460 |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t European journal of organic chemistry |d Weinheim : Wiley-VCH Verl., 1998 |g (2010), 16, Seite 3041-3048 |h Online-Ressource |w (DE-627)269534539 |w (DE-600)1475010-7 |w (DE-576)07788468X |x 1099-0690 |7 nnas |a Grafting organic n-semiconductors to surfaces (perfluoro-p-terphenyl-4-yl)alkanethiols |
| 773 | 1 | 8 | |g year:2010 |g number:16 |g pages:3041-3048 |g extent:8 |a Grafting organic n-semiconductors to surfaces (perfluoro-p-terphenyl-4-yl)alkanethiols |
| 856 | 4 | 0 | |u https://doi.org/10.1002/ejoc.201000151 |x Resolving-System |x Verlag |z lizenzpflichtig |3 Volltext |
| 856 | 4 | 0 | |u https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201000151 |x Verlag |z lizenzpflichtig |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20230704 | ||
| 993 | |a Article | ||
| 994 | |a 2010 | ||
| 998 | |g 1118537629 |a Zharnikov, Michael |m 1118537629:Zharnikov, Michael |d 120000 |d 120300 |e 120000PZ1118537629 |e 120300PZ1118537629 |k 0/120000/ |k 1/120000/120300/ |p 3 | ||
| 999 | |a KXP-PPN1851558314 |e 4348179913 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"relHost":[{"disp":"Grafting organic n-semiconductors to surfaces (perfluoro-p-terphenyl-4-yl)alkanethiolsEuropean journal of organic chemistry","part":{"year":"2010","extent":"8","issue":"16","text":"(2010), 16, Seite 3041-3048","pages":"3041-3048"},"pubHistory":["1998 -"],"type":{"media":"Online-Ressource","bibl":"periodical"},"recId":"269534539","title":[{"title":"European journal of organic chemistry","title_sort":"European journal of organic chemistry"}],"language":["eng"],"physDesc":[{"extent":"Online-Ressource"}],"note":["Gesehen am 21.01.04"],"id":{"zdb":["1475010-7"],"eki":["269534539"],"doi":["10.1002/(ISSN)1099-0690"],"issn":["1099-0690"]},"origin":[{"dateIssuedDisp":"1998-","dateIssuedKey":"1998","publisherPlace":"Weinheim","publisher":"Wiley-VCH Verl."}]}],"person":[{"given":"Björn","role":"aut","display":"Schüpbach, Björn","family":"Schüpbach"},{"given":"Michael","role":"aut","family":"Bolte","display":"Bolte, Michael"},{"role":"aut","family":"Zharnikov","display":"Zharnikov, Michael","given":"Michael"},{"role":"aut","display":"Terfort, Andreas","family":"Terfort","given":"Andreas"}],"type":{"media":"Online-Ressource","bibl":"article-journal"},"origin":[{"dateIssuedKey":"2010","dateIssuedDisp":"April 14, 2010"}],"recId":"1851558314","id":{"doi":["10.1002/ejoc.201000151"],"eki":["1851558314"]},"note":["Gesehen am 04.07.2023"],"name":{"displayForm":["Björn Schüpbach, Michael Bolte, Michael Zharnikov, and Andreas Terfort"]},"physDesc":[{"extent":"8 S."}],"language":["eng"],"title":[{"title":"Grafting organic n-semiconductors to surfaces","subtitle":"(perfluoro-p-terphenyl-4-yl)alkanethiols","title_sort":"Grafting organic n-semiconductors to surfaces"}]} | ||
| SRT | |a SCHUEPBACHGRAFTINGOR1420 | ||