Selective vicinal diiodination of polycyclic aromatic hydrocarbons

  • Vicinally diiodinated polycyclic aromatic hydrocarbons (I2‐PAHs) are accessible from the corresponding diborylated B2‐PAHs through boron/iodine exchange. The B2‐PAHs have been prepared via twofold electrophilic borylation reactions templated by a vicinally disilylated benzene. Our protocol is applicable to fluorenes, acenes, annulated acenes, oligoaryls, and even [5]helicene. Using B2‐naphthalene as the example, we have shown that the reaction scope can, in principle, be expanded to include the synthesis of vicinally dibrominated and dihydroxylated PAHs. The usefulness of the building blocks provided by our method in the field of optoelectronic materials was demonstrated by the successful conversion of I2‐fluoranthene to the analogous doubly alkynylated fluoranthene emitter.

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Author:Tanja Kaehler, Alexandra John, Tao Jin, Michael BolteORCiD, Hans-Wolfram LernerORCiDGND, Matthias WagnerORCiD
Parent Title (German):European Journal of Organic Chemistry
Publisher:Wiley-VCH Verl.
Place of publication:Weinheim
Document Type:Article
Date of Publication (online):2020/08/19
Date of first Publication:2020/08/19
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2020/12/08
Tag:Halogenation; Iodine; Polycyclic aromatic hydrocarbons; Synthetic methods
Page Number:5
First Page:5847
Last Page:5851
Institutes:Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Licence (German):License LogoCreative Commons - Namensnennung-Nicht kommerziell - Keine Bearbeitung 4.0