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) 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.
Djukic
Jean-Pierre
JP
Institut de Chimie de Strasbourg, UMR 7177, Laboratoire de Synthèses Métallo-Induites, Université Louis Pasteur, 4 rue Blaise Pascal, F-67000 Strasbourg, France. djukic@chimie.u-strasbg.fr
Michon
Christophe
C
Ratkovic
Zoran
Z
Kyritsakas-Gruber
Nathalie
N
de Cian
André
A
Pfeffer
Michel
M
D004563:Electrochemistry; D009682:Magnetic Resonance Spectroscopy; D008345:Manganese / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared
D009942:Organometallic Compounds; D011719:Pyrazines; D011743:Pyrimidines; D011810:Quinoxalines; D008345:Manganese