Antiaromatic Carbaporphyrinoids: Fluorene as a Fused Motif toward the Synthesis of meso-Fused Heterobenziporphyrins
Organic letters, 2019•ACS Publications
meso-Tetraphenyl meta-benziporphyrins are nonaromatic macrocycles which can be
changed to antiaromatic by fusing the core benzene ring with one of the adjacent meso-
phenyl groups, as demonstrated here by adopting a premodification method. We used a
fluorene moiety in place of the m-phenylene ring as a premodified fused aromatic motif to
synthesize fused heterobenziporphyrins. Spectral and X-ray data indicated that the
macrocycles are antiaromatic, which was supported by DFT, ACID, and NICS calculations …
changed to antiaromatic by fusing the core benzene ring with one of the adjacent meso-
phenyl groups, as demonstrated here by adopting a premodification method. We used a
fluorene moiety in place of the m-phenylene ring as a premodified fused aromatic motif to
synthesize fused heterobenziporphyrins. Spectral and X-ray data indicated that the
macrocycles are antiaromatic, which was supported by DFT, ACID, and NICS calculations …
meso-Tetraphenyl meta-benziporphyrins are nonaromatic macrocycles which can be changed to antiaromatic by fusing the core benzene ring with one of the adjacent meso-phenyl groups, as demonstrated here by adopting a premodification method. We used a fluorene moiety in place of the m-phenylene ring as a premodified fused aromatic motif to synthesize fused heterobenziporphyrins. Spectral and X-ray data indicated that the macrocycles are antiaromatic, which was supported by DFT, ACID, and NICS calculations. These macrocycles formed organopalladium complexes.
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