Perylenophthalocyanines
FULL PAPER
22: Yield 0.19 g, 16%; m.p. >3008C; 1H NMR (300 MHz, C2D2Cl4,
708C): d=0.80 (t, J=7.0 Hz, 6H), 1.13–1.31 (m, 12H), 1.50–1.75 (m,
4H), 3.07 (t, J=7.7 Hz, 4H), 8.03 (dd, J=8.2, 7.9 Hz, 2H), 8.21 (d, J=
8.2 Hz, 2H), 8.35 (s, 2H), 8.85 ppm (d, J=7.9 Hz, 2H); n˜max (Nujol)=
1830, 1761 cmÀ1; HR-MS (EI): calcd for C36H34O3: 514.2508; found:
514.2515.
Acknowledgements
Support from the EPSRC Mass Spectrometry Service Centre (Swansea)
is gratefully acknowledged.
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Function, CUP, Cambridge, 1998.
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22 and 23: 3,10-Dihexylperylene 15 (1.00 g, 2.36 mmol), chloranil (0.58 g,
2.36 mmol), fumaronitrile (2.0 g, 0.036 mol) and CHCl3 (2 mL) were
heated in a sealed tube at 1408C for 96 h. After cooling, the mixture was
purified by column chromatography (silica gel, CH2Cl2/light petroleum)
and recrystallisation from pentanol. 22: Yield 0.05 g, 5%; m.p. >3008C;
1H NMR (300 MHz, CDCl3): 0.95 (t, J=7.2 Hz, 6H), 1.39–1.61 (m, 12H),
1.81–1.87 (m, 4H), 3.12 (t, J=7.3 Hz, 4H), 7.75 (s, 2H), 8.11 (dd, J=8.0,
7.3 Hz, 2H), 8.26 (d, J=8.0 Hz, 2H), 8.89 ppm (d, J=7.3 Hz, 2H); n˜max
(Nujol)=2221 cmÀ1; HR-MS (EI): calcd for C36H34N2: 494.2722; found:
494.2723; 23: Yield 0.02 g, 2%; m.p. >3008C; 1H NMR (300 MHz,
CDCl3): d=0.93 (t, J=7.1 Hz, 6H), 1.25–1.56 (m, 12H), 1.77–1.84 (m,
4H), 3.16 (t, J=7.4 Hz, 4H), 7.53 (d, J=9.2 Hz, 2H), 7.80 (d, J=8.0 Hz,
2H), 7.84 (d, J=9.2 Hz, 2H), 8.53 Hz (d, J=8.0 Hz, 2H); 13C NMR
(75 MHz, CDCl3): d=14.0, 22.6, 29.5, 31.1, 31.7, 33.2, 109.9, 115.3, 121.3,
122.3, 122.5, 125.9, 126.6, 127.8, 128.2, 129.2, 129.3, 139.3 ppm; n˜max
(Nujol)=2225 cmÀ1; HR-MS (EI): calcd for C36H34N2: 494.2722; found:
494.2705.
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1993, 105, 1722–1724; Angew. Chem. Int. Ed. Engl. 1993, 32, 1660–
1662.
24: Synthesised as above; Yield 1%, m.p. >3008C; 1H NMR (300 MHz,
CDCl3): d=0.89 (t, J=7.3 Hz, 6H), 1.25–1.61 (m, 36H), 1.81–1.92 (m,
4H), 3.28 (t, J=6.6 Hz, 4H), 7.75 (s, 2H), 8.18 (dd, J=7.9, 7.1 Hz, 2H),
8.45 (d, J=7.9 Hz, 2H), 9.12 (d, J=7.1 Hz, 2H); n˜max (Nujol)
=2224 cmÀ1; HR-MS (EI): calcd for C48H58N2: 662.4600; found: 662.4596.
25: Dinitrile 22 (0.30 g, 0.60 mmol), DBU (0.06 g, 0.40 mmol) and zinc
acetate (0.02 g, 0.15 mmol) were stirred in refluxing hexanol for 24 h.
After the mixture had been cooled, the precipitate was filtered off, ex-
tracted (Soxhlet) with pyridine/THF and reprecipitated repeatedly
(THF). Yield 12 mg, 4%, m.p. >3008C; lmax (THF)=797 nm (e= 1.36
105); MS (MALDI): m/z: 2044 ([M]+, 100%).
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2655.
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1771–1776.
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28: Dinitrile 22 (0.30 g, 0.6 mmol), 3,6-dihexylphthalonitrile 27 (1.61 g,
5.4 mmol), DBU (0.70 g, 4.5 mmol) and zinc acetate (0.6 g, 2.6 mmol)
were stirred in refluxing hexanol for 24 h. After the mixture had been
cooled, the precipitate was filtered off and purified by column chroma-
tography (silica gel, CH2Cl2/light petroleum, THF/light petroleum) and
recrystallisation from THF/MeOH). Yield 16 mg, 5%; m.p. 2908C;
1H NMR (400 MHz, C2D2Cl4, 708C): 0.23 (t, J=7.3 Hz, 6H), 0.74–1.88
(m, 68H), 2.05–2.43 (m, 8H), 3.29–3.41 (brs, 4H), 4.45–4.90 (3brs,
12H), 7.03–7.45 (3brs, 6H), 7.78–7.85 (2brm, 4H), 8.00 (brs, 2H),
10.51 ppm (brs, 2H); lmax (THF)
(MALDI): m/z: 1449 ([M]+).
=
746 nm (e=1.73105); MS
Received: June 21, 2006
Published online: September 5, 2006
Chem. Eur. J. 2006, 12, 8609 – 8613
ꢀ 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
8613