The research focus is the development of the chemistry of azaperylenes with hitherto non-accessible CH/N substitution patterns. The aim in this context is an access to redox-active molecules which may act as multi-electron reservoirs or electron acceptors in n-channel semiconductors. Another focus is the synthesis of chiral fluorophors and their investigation as emitters of circular polarized light for applications in optoelectronic devices. Tetraazaperylene compounds, which act as solid state luminophores, are grafted covalently onto photopolymerizable monomers, in order to fabricate micro-structured building blocks for the construction of micro-antennas and other devices.
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Feb 20, 2024
Eichelmann, Robert; Rippel, Daniel; Ballmann, Joachim; Gade, Lutz H., 2024, "Zipping up Tetraazaperylene: Synthesis of Tetraazacoronenes via Double Coupling in the Bay Positions [data]",, heiDATA, V1
Substituted tetraazacoronene fluorophores have been obtained selectively by double Suzuki–Miyaura cross coupling of symmetrically substituted 1,2-bis(pinacolatoboryl)alkenes with a bay-substituted octaazaperopyrenedioxide (OAPPDO). Subsequent Scholl reaction of the dimethoxypheny...
Feb 20, 2024
Eichelmann, Robert; Jeudy, Pierre; Schneider, Lars; Zerhoch, Jonathan; Mayer, Paula R.; Ballmann, Joachim; Deschler, Felix; Gade, Lutz H., 2024, "Chiral Bay-Alkynylated Tetraazaperylenes: Photophysics and Chiroptical Properties",, heiDATA, V1
Fully bay-alkynylated octaazaperopyrene dioxide (OAPPDO) derivatives were accessible through Stille cross coupling reaction of the corresponding bay-chlorinated derivatives. This steric congestion of the bay area led to helically chiral fluorophores, and chiral resolution of two...
Feb 20, 2024
Eichelmann, Robert; Ballmann, Joachim; Gade, Lutz H., 2024, "Tetraazacoronenes and Their Dimers, Trimers and Tetramers [data]",, heiDATA, V1
Tetraazacoronenes were synthesized from bay-functionalized tetraazaperylenes by Zr-mediated cyclization and four-fold Suzuki–Miyaura cross coupling. In the Zr-mediated approach, an η4-cyclobutadiene-zirconium(IV) complex was isolated as an intermediate to cyclobutene-annulated de...
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