Synthesis of phenylethyne-linked porphyrin dyads

Four new porphyrin dyads have been prepared for studies in artificial photosynthesis. The two porphyrins are joined at the meso positions via a phenylethyne linker and are present in zinc/zinc or zinc/free base metalation states. The porphyrin bearing the ethynyl unit incorporates zero, one, or two...

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Bibliographic Details
Published inTetrahedron Vol. 60; no. 9; pp. 2011 - 2023
Main Authors Tomizaki, Kin-ya, Lysenko, Andrey B, Taniguchi, Masahiko, Lindsey, Jonathan S
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.02.2004
Elsevier
Subjects
Chemistry
Chemistry, Organic
Dipyrromethane
Energy transfer
Ethyne
Phenylethyne
Physical Sciences
Porphyrin
Science & Technology
Phenylethyne
Porphyrin
Ethyne
Energy transfer
Dipyrromethane
porphyrin
COMPLEXES
energy transfer
MULTIPORPHYRIN ARRAYS
MESOSUBSTITUTED PORPHYRINS
ORGANOLITHIUM REAGENTS
DIMERS
ELECTRON-TRANSFER
phenylethyne
ethyne
ENERGY-TRANSFER
dipyrromethane
TRIPLET EXCITED-STATES
5,10,15,20-TETRAARYLETHYNYL-SUBSTITUTED PORPHYRINS
5,10,15-TRISUBSTITUTED PORPHYRINS
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Summary:Four new porphyrin dyads have been prepared for studies in artificial photosynthesis. The two porphyrins are joined at the meso positions via a phenylethyne linker and are present in zinc/zinc or zinc/free base metalation states. The porphyrin bearing the ethynyl unit incorporates zero, one, or two pentafluorophenyl groups at non-linking meso positions for tuning the porphyrin redox potentials. The synthetic approach entailed Pd-mediated coupling of porphyrin building blocks that bear a single ethynylphenyl or bromo/iodo substituent. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.01.003