University of Oulu

Dalton Trans., 2020,49, 15339-15354,

Chelated Fischer carbene complexes of annulated thiophenes : synthesis, structure and electrochemistry

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Author: Lamprecht, Zandria1; Malan, Frederick P.1; Fernández, Israel2;
Organizations: 1Department of Chemistry, University of Pretoria, Private Bag X20, Hatfield 0028, Pretoria, South Africa
2Departamento de Química Orgánica I and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Madrid, Spain
3Laboratory of Inorganic Chemistry, Environmental and Chemical Engineering, University of Oulu, P. O. Box 3000, 90014 Oulu, Finland
Format: article
Version: published version
Access: open
Online Access: PDF Full Text (PDF, 3.4 MB)
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Language: English
Published: Royal Society of Chemistry, 2020
Publish Date: 2020-11-25


Two (thieno[3,2-b]thiophene) and three annulated thiophenes (dithieno[2,3-b;3′,2′-d]thiophene and dithieno[3,2-b;2′,3′-d]thiophene) were employed as building blocks to synthesize linear or semi-circular chelated mononuclear biscarbene and dinuclear tetracarbene complexes. The electronic properties of the annulated thienylene chelated carbene complexes were investigated by cyclic voltammetry experiments and compared to non-chelated Fischer-type monocarbene complexes. Density functional theory (DFT) calculations were used to assign the redox events and to probe the extent of electron delocalisation as well as the possibility of electronic (intramolecular metal–metal) communication as a result of intervalence. The differences of these electronic properties in the conjugated chelated carbene complexes are compared to chelated carbene compounds without a linear conjugated pathway.

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Series: Dalton transactions
ISSN: 1477-9226
ISSN-E: 1477-9234
ISSN-L: 1477-9226
Volume: 49
Issue: 43
Pages: 15339 - 15354
DOI: 10.1039/d0dt03298k
Type of Publication: A1 Journal article – refereed
Field of Science: 116 Chemical sciences
Funding: The authors gratefully acknowledge the National Research Foundation, South Africa (NRF 105740; NRF 105529, NRF 87788 and NRF 9772) and Sasol Technology R&D Pty. Ltd. (South Africa) for financial support. I. F. acknowledges support from the Spanish MINECO (CTQ2016-78205-P, CTQ2016-81797-REDC and PID2019-106184GB-I00).
Copyright information: © The Royal Society of Chemistry 2020. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.