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Synthesis of BODIPY‐Appended Subporphyrins
Author(s) -
Sugimoto Hisashi,
Muto Masahiro,
Tanaka Takayuki,
Osuka Atsuhiro
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001188
Subject(s) - bodipy , chemistry , sonogashira coupling , biphenylene , intramolecular force , porphyrin , fluorescence , stereochemistry , photochemistry , phenylene , palladium , combinatorial chemistry , catalysis , organic chemistry , physics , polymer , quantum mechanics
BODIPY–subporphyrin hybrids bridged by a 1,4‐biphenylene or 1,4‐diphenylethynylene spacer were synthesized either by the palladium‐catalyzed Suzuki–Miyaura reaction or the Sonogashira reaction. Their structural and optical properties were examined with respect to the bridge and BODIPY structures. In all cases, intramolecular excitationenergy transfer from the subporphyrin core to the BODIPY peripheries is efficient. Depending on the presence or absence of β‐methyl groups adjacent to the meso position of the BODIPY subunit, the fluorescence is either increased or decreased. It was also found that the electronic interaction between the subporphyrin core and the meso ‐(1,4‐phenylene) substituents causes spectral changes for the subporphyrin part, which is not observed for porphyrin counterparts.