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Synthesis and properties of novel extended BODIPYs with rigid skeletons

Author:
Kawamata, Yuki, Ito, Satoshi, Furuya, Masaru, Takahashi, Kai, Namai, Katsuya, Hashimoto, Saori, Roppongi, Makoto, Oba, Toru
Source:
Tetrahedron letters 2019 v.60 no.10 pp. 707-712
ISSN:
0040-4039
Subject:
Suzuki reaction, absorption, condensation reactions, fluorescence, heat, moieties, pyrroles, solubility, solvents
Abstract:
Novel extended BODIPYs fused with bicyclo rings were synthesized from bicyclopyrroles by combining Knoevenagel condensation, Suzuki coupling, and O-chelation. The absorption maxima of the BODIPYs ranged from the visible to near-infrared region and the compounds showed good solubility in organic solvents. The solubility of the bicycloBODIPY with 2-naphthyl groups at the α-position of the pyrrole units was particularly high. Heating converted distyrylBODIPY with bicyclo[2.2.2]octene to benzoBODIPY with absorption (748.5 nm) and fluorescence (775.0 nm) in the near-infrared region.
Agid:
6301309