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- Title
Synthesis of Phenalenyl-Fused Pyrylium Cations: Divergent C−H Activation/Annulation Reaction Sequence of Naphthalene Aldehydes with Alkynes.
- Authors
Yin, Jiangliang; Tan, Meiling; Wu, Di; Jiang, Ruyong; Li, Chengming; You, Jingsong
- Abstract
Described herein is the synthesis of stable oxonium-doped polycyclic aromatic hydrocarbons (PAHs) by the rhodium-catalyzed C−H activation/annulations of naphthalene-type aldehydes with internal alkynes. This protocol provides four divergent reaction types, including two unexpected annulations with an oxygen transposition process, which lead to diverse types of phenalenyl-fused pyrylium cations comprising a four-, five-, or six-ring-fused π-conjugated core. The annulations exhibit an exquisite regioselectivity and a high tolerance of sensitive functional groups. These PAHs feature intriguing photophysical properties such as full-color tunable fluorescence emission, high quantum yield, and positively charged core, and can be reduced easily to the phenalenyl radicals.
- Subjects
FLUOROHYDROCARBONS; ORGANIC chemistry; AROMATIC compounds; FLUORESCENCE; PHOTOLUMINESCENCE
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 42, p13274
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201708127