Issue 14, 1992

Molecular materials containig donor and acceptor groups. Synthesis, structure and spectroscopic properties of ferrocenyl Schiff bases

Abstract

Ferrocenyl Schiff-base derivatives of the form [Fe(η-C5H5)(η-C5H4CH[double bond, length half m-dash]NR)][R = NCH(C6H4NO2-p)1, C6H4CN-p2, C6H4NO2-p3, C6H4F-p4, C6H4Cl-p5, C6H4Br-p6, C6H4NO2-m7, NH(C6H4NO2-o)8, NH(C6H4NO2-p)9 or NH(C6F5)10], have been prepared from ferrocenecarbaldehyde. Proton, 13C NMR, UV/VIS and 57Fe Mössbauer spectroscopic data are presented. A number of these derivatives contain the donor–π-acceptor-(D–π-A) structural motif desired for non-linear optical materials. The behaviour of the ferrocenyl moiety as a donor is compared to that of the 4-dimethylaminophenyl group. The UV/VIS spectra of compound 1 showed considerable solvatochromism. As a result of this and its extended donor–π-acceptor nature, 1 was tested for non-linear optical properties, specifically, second harmonic generation. The results, however, were negative. A single-crystal X-ray study revealed 1 to crystallize in a centrosymmetric space group P21/n, with a= 5.885(1), b= 30.745(3), c= 8.662(1)Å, β= 96.40(2)° and Z= 4. The most striking feature of the molecular structure is the coplanarity of the substituent group with the η-C5H4 ring of the ferrocenyl moiety. The crystal structure reveals stacks of ferrocenyl, phenyl, phenyl, ferrocenyl moieties with inter-ring distances of 3.529 Å between the C5–C6 rings and 3.478 Å between the C6–C6 ring planes. The observation of a DAAD in contrast to a DADA stack is discussed.

Article information

Article type
Paper

J. Chem. Soc., Dalton Trans., 1992, 2235-2241

Molecular materials containig donor and acceptor groups. Synthesis, structure and spectroscopic properties of ferrocenyl Schiff bases

A. Houlton, N. Jasim, R. M. G. Roberts, J. Silver, D. Cunningham, P. McArdle and T. Higgins, J. Chem. Soc., Dalton Trans., 1992, 2235 DOI: 10.1039/DT9920002235

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