Electronic and NMR properties of meso-monosubstituted ferrocenylporphyrin: evidence of pi-conjugation between porphyrin and ferrocene

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The reaction of dipyrrylmethane with an equimolar mixture of ferrocenecarboxaldehyde and benzaldehyde in dry acetonitrile in the presence of a catalytic amount of trichloroacetic acid leads to the formation of 5-ferrocenyl-15-phenyl-2,8,12,18-tetraethyl-3,7,13, 17-tetramethylporphyrin (1) with a yield of 27%. The metallation of 1 with Zn(OAc)(2). 2H(2)O and MnCl2. 4H(2)O gives Zn(.)1 and MnCl(.)1, respectively. Cyclic voltammograms of 1, Zn(.)1 and MnCl(.)1 show reversible one-electron oxidation processes for the oxidation of ferrocene at 0.29. 0.22, and 0.37 V, respectively. Variable temperature H-1 NMR spectra of 1 in toluene-d(s) show two distinct singlets of equal intensities and line widths for NH protons. From the plot of In (k/T) versus 1/T according to the Eyring equation, gave straight line with Delta G(double dagger) = 51 kJ mol(-1). (C) 2000 Elsevier Science Ltd. All rights reserved.
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Issue Date
2000-09
Language
English
Article Type
Article
Keywords

LINKED PORPHYRIN; NONPLANAR PORPHYRINS; ENERGY-TRANSFER; COMMUNICATION; CHARGE; DIMERS

Citation

POLYHEDRON, v.19, no.16-17, pp.1961 - 1966

ISSN
0277-5387
URI
http://hdl.handle.net/10203/2108
Appears in Collection
CH-Journal Papers(저널논문)
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