Supramolecular Chemistry
FULL PAPER
NH4PF6 was added to the solution and the precipitate was collected. The
solid was purified by recrystallization from acetonitrile/Et2O to afford 2c
(19 mg, 59%) as a green solid. M.p. >3008C; 1H NMR (400 MHz,
CD3CN): d=8.73 (d, J=7.8 Hz, 4H; HM), 8.52–8.46 (m, 6H; HN, HL),
8.28 (s, 2H; HF), 7.98 (td, J=1.5, 7.8 Hz, 4H; HK), 7.91 (d, J=5.9 Hz,
4H; HI), 7.66 (ddd, J=1.0, 7.3, 8.8 Hz, 2H; HC), 7.27 (ddd, J=1.0, 5.4,
6.9 Hz, 4H; HJ), 7.15 (d, J=8.8 Hz, 2H; HD), 7.14 (s, 2H; HG), 6.78 (dd,
J=1.0, 6.0 Hz, 2H; HA), 6.65–6.61 (m, 2H; HB), 3.98 ppm (s, 6H; HE);
IR (KBr): n˜ =3095 (w), 1605 (m), 1509 (s), 1468 (s), 1404 (s), 1317 (m),
1198 (m), 1036 (w), 837 (s), 766 (s), 557 cmꢀ1 (s); UV/Vis (CH3CN):
lmax =272, 280, 304, 440, 614, 772 nm; ES-MS: m/z calcd for [Ru2(1c)-
(terpy)2(PF6)3]+ =[C48H40F18N14P3Ru2]+: 1451.1, found: 1451.0.
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2,5-Pyrazinedicarboxaldehyde (4): Compound 4 was prepared by ozono-
lysis of 6, as previously described.[10] It was purified by recrystallization
(reprecipitation) from a CHCl3/iPr2O mixture. Yield 20–30%; yellowish
solid; m.p. 124–1258C; 1H NMR (400 MHz, CDCl3): d=10.23 (s, 2H),
9.30 ppm (s, 2H); 13C NMR (100 MHz, CDCl3): d=191.79, 148.77,
143.41 ppm; UV/Vis (CHCl3): lmax =280 nm; EI-MS: m/z (%): 136.1
(100) [M]+, 107.1 (47) [Mꢀ29]+, 80.0 (12) [Mꢀ56]+, 52.1 (34) [Mꢀ84]+,
29.1 (11) [Mꢀ107]+; HRMS (EI-MS): calcd for [C6H4O2N2]+:136.0273;
found: 136.0275.
2,5-(E,E)-Distyrylpyrazine (6): Compound 6 was prepared by condensa-
tion of benzaldehyde with 2,5-dimethylpyrazine, as previously de-
scribed.[9] Yellow solid; m. p. 2248C; 1H NMR (300 MHz, CDCl3): d=
8.60 (s, 2H), 7.74 (d, J=16.1 Hz, 2H), 7.61 (d, J=7.2 Hz, 4H), 7.44–7.30
(m, 6H), 7.18 ppm (d, J=16.1 Hz, 2H); 13C NMR (75 MHz, CDCl3): d=
149.24, 143.42, 136.42, 134.53, 128.99, 127.44, 124.25 ppm (two overlaping
peaks); UV/Vis (CHCl3): lmax =305, 384 nm.
Acknowledgements
We thank Dr. Annie Marquis and Raymond Hueber for mass spectrome-
try analyses. A.-M.S. thanks le Ministꢆre de la Recherche, de la Jeunesse
et de la Technologie for a predoctoral fellowship. S.C. also acknowledges
MIUR and FIRB for financial support.
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Received: December 8, 2004
Published online: April 21, 2005
Chem. Eur. J. 2005, 11, 3997 – 4009
ꢂ 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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