期刊
TETRAHEDRON LETTERS
卷 51, 期 34, 页码 4505-4508出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.06.096
关键词
Porphyrins; Porphyrinoids; Chlorins; Chlorin analogues; Pyrrole-modified porphyrins
资金
- NSF [CHE-0517782, CMMI-0730826]
- US Air Force
The formal replacement of one of the pyrrole rings in [meso-tetraphenylporphyrinato]Ni(II) (5Ni) by an azete moiety is reported. Thus, reaction of known chlorophin monoaldehyde 7Ni (made in three steps from 5Ni) with methyl-Grignard, followed by an acid-catalyzed ring-closure reaction, generates the title compound [meso-tetraphenyl-2-methylazeteochlorinato]Ni(II) (10Ni) in a rational and scalable process in good yields. The UV-vis spectroscopic properties of this chromophore are, as expected for this chlorin analogue, red-shifted when compared to the corresponding [porphyrinato]Ni(11) (5Ni) complex. A much improved synthesis of the starting material 7Ni by Vilsmeier-Haack formylation of [meso-tetraphenylchlorophinato]Ni(II) (8Ni) is also reported. (C) 2010 Elsevier Ltd. All rights reserved.
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