M. Brewis et al. / Tetrahedron 59 (2003) 3863–3872
3871
phthalocyaninatosilicon or dichloronaphthalocyaninato-
silicon as precursors, respectively.
J¼8 Hz, 16H), 3.62 (t, J¼8 Hz, 16H), 3.51 (t, J¼8 Hz,
16H), 3.33 (s, 24H), 0.01 (s, 4H). FAB-MS m/z¼2677
(MþHþ). GPC (vs polystyrene standards): 3300. Anal.
calcd for C146H174N8O38: C 65.50, H 6.55, N 4.19. Found C
64.98, H 6.45, N 4.12.
4.6.2. Di-(30,50-di-(300,500-di-[1000,4000,7000,10000-tetraoxaunde-
cyl])benzyloxy)-benzyloxyphthalocyaninatosilicon
([G2]2SiPc). The crude product was purified by column
chromatography (ethyl acetate with an increasing amount of
acetone) to give [G-2]2SiPc (27% yield) as a dark blue
viscous oil; UV/vis (CH2Cl2, nm): 679 (2.5£105), 650
4.6.6. Di-(30,50-di-(300,500-di-(3000,5000-(di-[10000,40000,70000,10000-tet-
raoxaundecyl])-benzyloxy)benzyloxy)benzyloxy-
naphthalocyaninatosilicon ([G3]2SiNc). The crude
product was purified by preparative TLC (DCM/ethanol)
to give [G-3]2SiNc (4% yield) as an olive-green oil; UV/vis
(CH2Cl2, nm): 793 (2.0£105), 730 (3.0£104), 695
1
(2.5£104), 610 (2£104), 354 (5£104). H NMR (500 MHz,
CDCl3) d ppm 9.58–9.51 (m, 8H), 8.33–8.27 (m, 8H), 6.36
(t, J¼2 Hz, 4H), 6.23 (d, J¼2 Hz, 8H), 5.64 (t, J¼2 Hz, 2H),
4.04 (t, J¼8 Hz, 16H), 3.96 (s, 8H), 3.82 (t, J¼8 Hz, 16H),
3.72 (t, J¼8 Hz, 16H), 3.67 (t, J¼8 Hz, 16H), 3.63 (t,
J¼8 Hz, 16H), 3.53 (t, J¼8 Hz, 16H), 3.48 (d, J¼2 Hz, 4H),
3.30 (s, 24H), 20.70 (s, 4H). FAB-MS m/z¼2499
(MþNaþ). GPC (vs polystyrene standards): 3100. Anal.
calcd for C130H166N8O38Si: C 63.04, H 6.74, N 4.52. Found
C 63.05, H 6.79, N 4.44.
1
(3.0£104), 438 (7£104), 370 (1£105). H NMR (500 MHz,
CDCl3) d ppm 10.01 (s, 8H), 8.55–8.52 (m, 8H), 7.81–7.78
(m, 8H), 6.64 (t, J¼2 Hz, 4H), 6.54 (br s, 16H), 6.41 (t,
J¼2 Hz, 8H), 5.58 (t, J¼2 Hz, 2H), 4.85 (br s, 16H), 4.06 (t,
J¼8 Hz, 32H), 3.94 (t, J¼2 Hz, 4H), 3.90 (s, 8H), 3.79 (t,
J¼8 Hz, 32H), 3.68 (t, J¼8 Hz, 32H), 3.66–3.60 (m, 64H),
3.50 (t, J¼8 Hz, 32H), 3.33 (s, 48H), 0.06 (s, 4H). MALDI-
MS m/z¼cluster centred at 4622 (Mþ). GPC (vs polystyrene
standards): 5600. Anal. calcd for C242H326N8O78Si: C
62.87, H 7.11, N 2.42. Found C 62.22, H 6.82, N 2.09.
4.6.3. Di-(30,50-di-(300,500-di-(3000,5000-(di-[10000,40000,70000,100000-tet-
raoxaundecyl])-benzyloxy)benzyloxy)benzyloxyphthalo-
cyaninatosilicon ([G3]2SiPc). The crude product was
purified by preparative TLC (DCM with an increasing
amount of ethanol) and to give [G-3]2SiPc (5% yield) as a
blue oil; UV/vis (CH2Cl2, nm): 680 (2.5£105), 650
Acknowledgements
1
(2.5£104), 610 (2£104), 354 (5£104). H NMR (500 MHz,
We thank EPSRC, Zeneca Specialities (now Avecia) and
BASF for financial support (M. B.).
CDCl3) d ppm 9.58–9.51 (m, 8H), 8.33–8.27 (m, 8H), 6.54
(t, J¼2 Hz, 16H), 6.46–6.42 (m, 12H), 6.30 (t, J¼2 Hz,
8H), 5.66 (t, J¼2 Hz, 2H), 4.90 (br s, 16H), 4.08 (t, J¼8 Hz,
32H), 3.98 (s, 8H), 3.81 (t, J¼8 Hz, 32H), 3.69 (t, J¼8 Hz,
32H), 3.67–3.60 (m, 64H), 3.50–3.45 (m, 36H), 3.33 (s,
48H), 20.72 (s, 4H). MALDI-MS m/z¼cluster centred at
4623 (Mþ). GPC (vs polystyrene standards): 3800. Anal.
calcd for C242H326N8O78Si: C 62.87, H 7.11, N 2.42. Found
C 62.44, H 6.95, N 2.19.
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1
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