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Kalashnikova et al.
1H NMR (CDCl3), δ: 5.11 (s, 4 H, CH2); 7.15 (s, 2 H, C6H2);
7.42 (m, 10 H, Ph). MS (EI, 70 eV), m/z: 448 [M]+.
References
4,5ꢀDibenzyloxyphthalonitrile (3). A mixture of 1,2ꢀdiꢀ
benzyloxyꢀ4,5ꢀdibromobenzene (2) (7.00 g, 0.016 mol) and
CuCN (4.90 g, 0.055 mol) was refluxed in dry DMF (80 mL) for
8 h. After cooling, the solvent was removed in vacuo, conc.
aqueous NH3 (300 mL) was added, and the mixture was vigorꢀ
ously stirred for a day. The precipitate was filtered off, washed
with water, and dried at 50 °C. The product was extracted with
CH2Cl2 in a Soxhlet apparatus. The extract was concentrated in
vacuo to give greenish crystals. Column chromatography on silica
gel with chloroform as an eluent followed by recrystallization
from ethanol gave compound 3 (2.78 g, 51%) as colorless crysꢀ
tals, m.p. 179—181 °C. Found (%): C, 77.38; H, 4.68; N, 8.17.
C22H16N2O2. Calculated (%): C, 77.63; H, 4.74; N, 8.23.
1H NMR (CDCl3), δ: 5.20 (s, 4 H, CH2); 7.13 (s, 2 H, C6H2);
7.38 (m, 10 H, Ph). MS (EI, 70 eV), m/z: 340 [M]+.
Lutetium(III) 2,3,9,10,16,17,23,24,2´,3´,9´,10´,16´,17´,
23´,24´ꢀhexadecabenzyloxy(diphthalocyanine) (4). A mixture of
4,5ꢀdibenzyloxyphthalonitrile (3) (340 mg, 1.00 mmol), luteꢀ
tium formate dihydrate (42 mg, 0.12 mmol), and DBU (106 mg,
0.70 mmol) was refluxed in nꢀhexanol (5 mL) under argon for 8 h.
After cooling, the product was filtered off and washed with
aqueous 70% MeOH. The residue was reprecipitated from
DMF with water and chromatographed on silica gel with benꢀ
zene—MeOH (10 : 1) as an eluent to remove resins. Additional
chromatography on Al2O3 gave complex 4 (153 mg, 44%) as
dark green crystals.
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Samarium(III) 2,3,9,10,16,17,23,24,2´,3´,9´,10´,16´,17´,
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This work was financially supported by the Internaꢀ
tional Scientific and Technical Center (Project No. 1526).
Received December 30, 2004;
in revised form April 13, 2005