Covalent Dimers of 1,3-Diphenylisobenzofuran for Singlet Fission: Synthesis and Electrochemistry

Date

2015-01-01

Author

Akdağ, Akın
Beran, Pavel
Rulisek, Lubomir
Dron, Paul I.
Ludvik, Jiri
Michl, Josef

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The synthesis of covalent dimers in which two 1,3-diphenylisobenzofuran units are connected through one phenyl substituent on each is reported. In three of the dimers, the subunits are linked directly, and in three others, they are linked via an alkane chain. A seventh new compound in which two 1,3-diphenylisobenzofuran units share a phenyl substituent is also described. These materials are needed for investigations of the singlet fission process, which promises to increase the efficiency of solar cells. The electrochemical oxidation and reduction of the monomer, two previously known dimers, and the seven new compounds have been examined, and reversible redox potentials have been compared with results obtained from density functional theory. Although the overall agreement is satisfactory, some discrepancies are noted and discussed.

Subject Keywords

Redox reactions, Oligomers, Electrodes, Mixtures, Oxidation

URI

https://hdl.handle.net/11511/56221

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo502004r

Collections

Department of Chemistry, Article

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Citation Formats

A. Akdağ, P. Beran, L. Rulisek, P. I. Dron, J. Ludvik, and J. Michl, “Covalent Dimers of 1,3-Diphenylisobenzofuran for Singlet Fission: Synthesis and Electrochemistry,” JOURNAL OF ORGANIC CHEMISTRY, pp. 80–89, 2015, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56221.