Ferrocenes with a Persulfurated Cyclopentadienyl Ring: Synthesis, Structural Studies, and Optoelectronic Properties
| Autor: | Harish Jangra, Konstantin Karaghiosoff, Peter M. Zehetmaier, Tobias Blockhaus, Karlheinz Sünkel, Fabian L. Zott, Christian Klein-Heßling |
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| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Metalation Chemistry Communication Organic Chemistry Intermolecular force metalation General Chemistry Crystal structure metallocenes 010402 general chemistry Ring (chemistry) Electrochemistry 01 natural sciences Communications Catalysis persulfurated arenes X-ray diffraction 0104 chemical sciences Crystallography Cyclopentadienyl complex Intramolecular force X-ray crystallography |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.201903033 |
| Popis: | Persulfurated arenes are a fascinating class of functional molecules with a wide range of potential applications. Ferrocenes are also a multifaceted class of aromatic compounds that can easily be finetuned for an enormous variety of desired properties. A combination of both substance classes might yield an even wider field of applications. Herein, we describe the synthesis of two ferrocenes with one persulfurated cyclopentadienyl ring [C5(SR)5], with R=Me or Ph, together with their crystal structures, optical, and electrochemical properties. Both crystal structures show significant intramolecular sulfur‐iron interactions as well as weak intermolecular sulfur– contacts. Cyclovoltammetry of the [C5(SPh)5] compound shows a high oxidation potential of 651 mV vs. FcH/FcH+. Metalation: Ferrocenes with one persulfurated cyclopentadienyl ring [C5(SR)5]FeCp have been prepared from monobromoferrocene by a sequence of deprotonations and electrophilic thiolations. In their crystal structures, all cyclopentadienyl rings have their thiolate substituents in axial positions away from the iron atom. Cyclovoltammetric studies show that the sulfur substituents lead to significantly enhanced oxidative stability (see figure). |
| Databáze: | OpenAIRE |
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