New manganese-scaffolded organic triple-deckers based on quinoxaline, pyrazine and pyrimidine cores

The thermolytic coupling of Ph(2)CN(2) and (t-Bu)(Ph)CN(2) with doubly cyclomanganated 2,5-diphenylpyrazine and 4,6-diphenylpyrimidine afforded substantial amounts of new triple decker compounds of either C(i) and C(2) symmetry respectively containing, in both series, two eta(3)-bonded Mn(CO)(3) fra...

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Published in:Dalton transactions : an international journal of inorganic chemistry 2006-01, Vol.2006 (12), p.1564-1573
Main Authors: Djukic, Jean-Pierre, Michon, Christophe, Ratkovic, Zoran, Kyritsakas-Gruber, Nathalie, de Cian, André, Pfeffer, Michel
Format: Article
Language:English
Subjects:
Electrochemistry
Magnetic Resonance Spectroscopy
Manganese - chemistry
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Pyrazines - chemical synthesis
Pyrazines - chemistry
Pyrimidines - chemical synthesis
Pyrimidines - chemistry
Quinoxalines - chemical synthesis
Quinoxalines - chemistry
Spectroscopy, Fourier Transform Infrared
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Summary:The thermolytic coupling of Ph(2)CN(2) and (t-Bu)(Ph)CN(2) with doubly cyclomanganated 2,5-diphenylpyrazine and 4,6-diphenylpyrimidine afforded substantial amounts of new triple decker compounds of either C(i) and C(2) symmetry respectively containing, in both series, two eta(3)-bonded Mn(CO)(3) fragments which intervene as scaffolds sustaining the helical non-conjugated triaryl backbone. The molecular structures of two pyrazine derivatives show a typical non-parallel stacking of the aromatic rings and the encapsulation of the central pyrazyl fragment with interplanar centroid-to-centroid distances of ca. 3.5 A. The stacking of the aromatics in the triple-decker pyrimidine derivatives has been assessed by (1)H NMR experiments at low temperature. All the triple-decker-type compounds are electroactive. Pyrimidine triple-deckers can reversibly be electrochemically reduced to the corresponding anions.
ISSN:1477-9226
0300-9246
1477-9234
DOI:10.1039/b513322j