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Deltoid versus Rhomboid: Controlling the Shape of Bis-ferrocene Macrocycles by the Bulkiness of the Substituents

Hoffmann, Viktor and Le Pleux, Loic and Haussinger, Daniel and Unke, Oliver T. and Prescimone, Alessandro and Mayor, Marcel. (2017) Deltoid versus Rhomboid: Controlling the Shape of Bis-ferrocene Macrocycles by the Bulkiness of the Substituents. Organometallics, 36 (4). pp. 858-866.

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Official URL: https://edoc.unibas.ch/63004/

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Abstract

Precise structural control of heteroannularly disubstituted ferrocene (Fc) structures is very challenging as the high rotational mobility of the Fc unit allows a large conformational diversity. Herein we present the syntheses, characterization, and electrochemical investigation of two complementary bis-ferrocene macrocycles, built up via Sonogashira cross coupling and intramolecular ring-closing reaction. While the X-ray structure of 1,2-ethynylbenzene bridged bis-ferrocene complex 1 shows a deltoidal conformation, a stretched oriented rhomboidal bis-ferrocene metallacycle 2 is formed when the peripheral benzene rings are decorated with bulky tert-butylsulfanyl groups. VT-NMR spectroscopy is used to assign the rotation of the embedded Fc units in rhomboid 2. Moreover, cyclic voltammetry (CV) of deltoid 1 and rhomboid 2 indicate that electronic communication between both ferrocenyl groups can be neglected, while the electrostatic through space coupling is significant.
Faculties and Departments:05 Faculty of Science > Departement Chemie
05 Faculty of Science > Departement Chemie > Chemie > Molecular Devices and Materials (Mayor)
05 Faculty of Science > Departement Chemie > Chemie > Nuclear Magnetic Resonance (Häussinger)
UniBasel Contributors:Mayor, Marcel and Hoffmann, Viktor and Le Pleux, Loïc and Unke, Oliver and Prescimone, Alessandro and Häussinger, Daniel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:0276-7333
e-ISSN:1520-6041
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:16 Apr 2018 06:41
Deposited On:16 Apr 2018 06:41

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