Details
| Original language | English |
|---|---|
| Pages (from-to) | 2388-2401 |
| Number of pages | 14 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2021 |
| Issue number | 17 |
| Early online date | 1 Apr 2021 |
| Publication status | Published - 5 May 2021 |
Abstract
Extended π systems based on 1,1′-aryl or (2-arylethynyl) disubstitution at ferrocene with thioate or dithioate end groups are reported. In the context of molecular electronics, such end groups are possible alternative end groups for the attachment of molecular wires at gold surfaces. The respective thioates were successfully prepared in high yields via the respective carboxylic acid derivatives. Subsequent treatment with Lawesson's reagent led to the respective dithioates. However, this did not work in the presence of triple bonds, in these cases, product mixtures were formed. On the basis of literature evidence with Woollin's reagent, the selenium analog of Lawesson's reagent, one product was tentatively characterized as a double cyclization product of two triple bonds and two molecules of Lawesson's reagent. Preliminary experiments towards the formation of gold complexes by reaction with a Johnphos gold(I) salt are included.
Keywords
- Extended π-Systems, Ferrocene, Gold Complexes, Synthetic methods
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, Vol. 2021, No. 17, 05.05.2021, p. 2388-2401.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - New π‐Extended 1,1′‐Disubstituted Ferrocenes with Thioate and Dithioate End Groups
AU - Schmiel, Sinem Fatma
AU - Butenschön, Holger
N1 - Funding Information: We thank Ms. Christina Schrand, M. Sc., for assistance in the synthesis of compound 17, and Dr. Gerald Dräger, Institut für Organische Chemie, Leibniz Universität Hannover, and Dr. Andreas Schaate, Institut f?r Anorganische Chemie, Leibniz Universität Hannover, for performing the crystal structure analyses. Open access funding enabled and organized by Projekt DEAL.
PY - 2021/5/5
Y1 - 2021/5/5
N2 - Extended π systems based on 1,1′-aryl or (2-arylethynyl) disubstitution at ferrocene with thioate or dithioate end groups are reported. In the context of molecular electronics, such end groups are possible alternative end groups for the attachment of molecular wires at gold surfaces. The respective thioates were successfully prepared in high yields via the respective carboxylic acid derivatives. Subsequent treatment with Lawesson's reagent led to the respective dithioates. However, this did not work in the presence of triple bonds, in these cases, product mixtures were formed. On the basis of literature evidence with Woollin's reagent, the selenium analog of Lawesson's reagent, one product was tentatively characterized as a double cyclization product of two triple bonds and two molecules of Lawesson's reagent. Preliminary experiments towards the formation of gold complexes by reaction with a Johnphos gold(I) salt are included.
AB - Extended π systems based on 1,1′-aryl or (2-arylethynyl) disubstitution at ferrocene with thioate or dithioate end groups are reported. In the context of molecular electronics, such end groups are possible alternative end groups for the attachment of molecular wires at gold surfaces. The respective thioates were successfully prepared in high yields via the respective carboxylic acid derivatives. Subsequent treatment with Lawesson's reagent led to the respective dithioates. However, this did not work in the presence of triple bonds, in these cases, product mixtures were formed. On the basis of literature evidence with Woollin's reagent, the selenium analog of Lawesson's reagent, one product was tentatively characterized as a double cyclization product of two triple bonds and two molecules of Lawesson's reagent. Preliminary experiments towards the formation of gold complexes by reaction with a Johnphos gold(I) salt are included.
KW - Extended π-Systems
KW - Ferrocene
KW - Gold Complexes
KW - Synthetic methods
UR - http://www.scopus.com/inward/record.url?scp=85108293187&partnerID=8YFLogxK
U2 - 10.1002/ejoc.202100335
DO - 10.1002/ejoc.202100335
M3 - Article
VL - 2021
SP - 2388
EP - 2401
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 0365-5490
IS - 17
ER -