Details
| Original language | English |
|---|---|
| Pages (from-to) | 1613-1619 |
| Number of pages | 7 |
| Journal | New Journal of Chemistry |
| Volume | 31 |
| Issue number | 9 |
| Publication status | Published - 1 Jan 2007 |
Abstract
Meso-substituted corroles bearing directly linked ferrocene unit have been synthesized for the first time. Among various methods studied, only the condensation of pentafluorophenyldipyrromethane with a formylferrocene led to this type of product. A triad containing corrole and porphyrin bridged with ferrocene has been obtained by a convergent approach. Bilanes were used as crucial substrates in the porphyrin-forming step. For the first time it was shown that H2O-MeOH-HCl conditions are suitable for preparation of various 10-(formylaryl)corroles via the direct condensation of aromatic dialdehydes with dipyrromethanes. Electrochemical studies of 10-ferrocenyl-5,15-bis(pentafluorophenyl)corrole support the possibility of intramolecular electron transfer from the corrole to the ferrocene system after the electrode oxidation of the ferrocene to a ferrocenium cation. We have studied the structure of 1-(corrolyl)-1′-(porphyrinyl)ferrocene by 1H NMR and UV-Vis. NMR spectra show that this compound has more conformational freedom than analogous, previously studied bis- porphyrinylferrocenes. Absorption spectra suggest the lack of strong electronic interaction between ferrocene and porphyrinoids for dyads and significant conjugation for the triad.
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- General Chemistry
- Materials Science(all)
- Materials Chemistry
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In: New Journal of Chemistry, Vol. 31, No. 9, 01.01.2007, p. 1613-1619.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis and properties of directly linked corrole-ferrocene systems
AU - Gryko, Daniel T.
AU - Piechowska, Joanna
AU - Jaworski, Jan S.
AU - Gałězowski, Michał
AU - Tasior, Mariusz
AU - Cembor, Marek
AU - Butenschön, Holger
PY - 2007/1/1
Y1 - 2007/1/1
N2 - Meso-substituted corroles bearing directly linked ferrocene unit have been synthesized for the first time. Among various methods studied, only the condensation of pentafluorophenyldipyrromethane with a formylferrocene led to this type of product. A triad containing corrole and porphyrin bridged with ferrocene has been obtained by a convergent approach. Bilanes were used as crucial substrates in the porphyrin-forming step. For the first time it was shown that H2O-MeOH-HCl conditions are suitable for preparation of various 10-(formylaryl)corroles via the direct condensation of aromatic dialdehydes with dipyrromethanes. Electrochemical studies of 10-ferrocenyl-5,15-bis(pentafluorophenyl)corrole support the possibility of intramolecular electron transfer from the corrole to the ferrocene system after the electrode oxidation of the ferrocene to a ferrocenium cation. We have studied the structure of 1-(corrolyl)-1′-(porphyrinyl)ferrocene by 1H NMR and UV-Vis. NMR spectra show that this compound has more conformational freedom than analogous, previously studied bis- porphyrinylferrocenes. Absorption spectra suggest the lack of strong electronic interaction between ferrocene and porphyrinoids for dyads and significant conjugation for the triad.
AB - Meso-substituted corroles bearing directly linked ferrocene unit have been synthesized for the first time. Among various methods studied, only the condensation of pentafluorophenyldipyrromethane with a formylferrocene led to this type of product. A triad containing corrole and porphyrin bridged with ferrocene has been obtained by a convergent approach. Bilanes were used as crucial substrates in the porphyrin-forming step. For the first time it was shown that H2O-MeOH-HCl conditions are suitable for preparation of various 10-(formylaryl)corroles via the direct condensation of aromatic dialdehydes with dipyrromethanes. Electrochemical studies of 10-ferrocenyl-5,15-bis(pentafluorophenyl)corrole support the possibility of intramolecular electron transfer from the corrole to the ferrocene system after the electrode oxidation of the ferrocene to a ferrocenium cation. We have studied the structure of 1-(corrolyl)-1′-(porphyrinyl)ferrocene by 1H NMR and UV-Vis. NMR spectra show that this compound has more conformational freedom than analogous, previously studied bis- porphyrinylferrocenes. Absorption spectra suggest the lack of strong electronic interaction between ferrocene and porphyrinoids for dyads and significant conjugation for the triad.
UR - http://www.scopus.com/inward/record.url?scp=34548262580&partnerID=8YFLogxK
U2 - 10.1039/b618631a
DO - 10.1039/b618631a
M3 - Article
AN - SCOPUS:34548262580
VL - 31
SP - 1613
EP - 1619
JO - New Journal of Chemistry
JF - New Journal of Chemistry
SN - 1144-0546
IS - 9
ER -