Synthesis of Geometrically Well-Defined Covalent Acene Dimers for Mechanistic Exploration of Singlet Fission

Synthesis of Geometrically Well-Defined Covalent Acene Dimers for Mechanistic Exploration of Singlet Fission

We report the first synthesis of norbornyl-bridged acene dimers (2 and 3) with well-defined and controlled spatial relationships between the acene chromophore subunits. We employ a modular 2-D strategy wherein the central module, common to all our compounds, is a norbornyl moiety. The acenes are att...

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Veröffentlicht in:Journal of organic chemistry 2017-05, Vol.82 (9), p.4866-4874
Hauptverfasser: Carey, Thomas J, Snyder, Jamie L, Miller, Ethan G, Sammakia, Tarek, Damrauer, Niels H
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INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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container_end_page 4874
container_issue 9
container_start_page 4866
container_title Journal of organic chemistry
container_volume 82
creator Carey, Thomas J
Snyder, Jamie L
Miller, Ethan G
Sammakia, Tarek
Damrauer, Niels H
description We report the first synthesis of norbornyl-bridged acene dimers (2 and 3) with well-defined and controlled spatial relationships between the acene chromophore subunits. We employ a modular 2-D strategy wherein the central module, common to all our compounds, is a norbornyl moiety. The acenes are attached to this module using the Diels–Alder reaction, which also forms one of the acene rings. Manipulation of the Diels–Alder adducts provides the desired geometrically defined bis-acenes. The modular nature of this synthesis affords flexibility and allows for the preparation of a variety of acene dimers, including functionalized tetracene dimers.
doi_str_mv 10.1021/acs.joc.7b00602
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title Synthesis of Geometrically Well-Defined Covalent Acene Dimers for Mechanistic Exploration of Singlet Fission
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