Octadecyldimethylchlorosilane → Bis(dimethyl-octadecyl-siloxy)germanium phthalocyanine

HRID 1708359Notes

Reaction equation

HRID 1708359 reaction equation
[CH3:1][Si:2]([CH3:22])([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])Cl.[OH:23][Ge:24][OH:25].[CH:26]1[CH:27]=[CH:28][C:29]2[C:30](=[C:32]3[N:64]=[C:63]4[N:65]=[C:56]([C:57]5[CH:58]=[CH:59][CH:60]=[CH:61][C:62]=54)[N:55]=[C:53]4[NH:54][C:46]([C:47]5[CH:48]=[CH:49][CH:50]=[CH:51][C:52]=54)=[N:45][C:43]4=[N:44][C:36]([C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][C:42]=54)=[N:35][C:34]=2[NH:33]3)[CH:31]=1>N1C=CC=CC=1>[CH3:1][Si:2]([CH3:22])([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[O:23][Ge:24][O:25][Si:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][CH2:57][CH3:56])([CH3:1])[CH3:22].[CH:27]1[CH:26]=[CH:31][C:30]2[C:29](=[C:34]3[N:35]=[C:36]4[N:44]=[C:43]([C:42]5[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=54)[N:45]=[C:46]4[NH:54][C:53]([C:52]5[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=54)=[N:55][C:56]4=[N:65][C:63]([C:62]5[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=54)=[N:64][C:32]=2[NH:33]3)[CH:28]=1

Participants

4

Reactant 2

HCID 87738OctadecyldimethylchlorosilaneHCID 178526211HCID 178526211, compound

Product 1

HCID 137226509Bis(dimethyl-octadecyl-siloxy)germanium phthalocyanine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In analogy to a procedure by Wheeler et.al., J. Am. Chem. Soc. 106, 7404 (1984)] 3.3 g (9.5 mmol)of dimethyl-octadecyl-chlorosilane and 0.5 g (0.8 mmol) of dihydroxygermanium-phthalocyanine in 50 ml of pyridine are stirred for 2 hours at 50°. The solution is cooled and filtered using a suction filter. The solvent is removed in vacuo, and 250 ml of hexane are added to the residue. The resulting precipitate is filtered off with suction and washed fast with hexane, then in portions with 200 ml of acetone/water (1:1). The residue is dried overnight under a high vacuum, then extracted with toluene in a Soxhlet, freed of solvent and dried, yielding bis(dimethyl-octadecyl-siloxy)germanium-phthalocyanine; NMR (pyridine-d5): δ=9.8-9.9 (m, 8H); 8.3-8.5 (m,8H): aromatic H's; 0.75-1.46 (various m's); 0.45(m); -0.03 (m); -0.88 (m); -1.91 (m); -2.48 (m, 4×CH3 : silyl side chains) ppm.

Workup

  1. temperatureThe solution is cooled
  2. filtrationfiltered
  3. filtrationfilter
  4. customThe solvent is removed in vacuo, and 250 ml of hexane
  5. additionare added to the residue
  6. filtrationThe resulting precipitate is filtered off with suction
  7. washwashed fast with hexane
  8. customThe residue is dried overnight under a high vacuum
  9. extractionextracted with toluene in a Soxhlet
  10. customdried

Sources & evidence

ORD record
ord-877c980e1c9d4a3bb90424c6a8b25e4d
Source dataset
uspto-grants-1994_10
Patent number
US05358940

Reaction notes

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