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Synthesis and Functionalization of Germanium Triphenylcorrolate: The First Example of a Partially Brominated Corrole
Author(s) -
Nardis Sara,
Mandoj Federica,
Paolesse Roberto,
Fronczek Frank R.,
Smith Kevin M.,
Prodi Luca,
Montalti Marco,
Battistini Gionata
Publication year - 2007
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200700184
Subject(s) - chemistry , corrole , derivative (finance) , regioselectivity , germanium , tetrapyrrole , quantum yield , yield (engineering) , dimer , ring (chemistry) , fluorescence , photochemistry , medicinal chemistry , organic chemistry , catalysis , silicon , physics , quantum mechanics , financial economics , economics , metallurgy , enzyme , materials science
Ge complexes of 5,10,15‐triphenylcorrole were prepared in refluxing dry DMF using GeCl 4 as the source of Ge. Chromatographic separation of the crude reaction mixture afforded the μ‐oxo dimer 1 and the methoxy derivative 2a . The corresponding chloride 2b can be obtained by treatment of 1 or 2a with HCl. The reaction of 2a with Br 2 in CHCl 3 /py afforded the hexabromo derivative 3 as the main product, giving the first indication of the regioselective substitution of pyrroles B and C on the corrole ring. The fully brominated open‐chain tetrapyrrole 4 was also characterized as a reaction by‐product. Different partially brominated Ge complexes 5 and 6 have been obtained by variation of reaction conditions, while the heptabromo derivative was obtained in a mixture with the corresponding fully brominated Gecorrole. Photophysical characterization of Ge corrolates confirmed the high fluorescence quantum yield of such complexes, and also led to the first observation of phosphorescence emissions from corrole complexes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)