Diphenylhexadecyloxysilanol → Bis(diphenylhexadecyloxy-siloxy)germanium phthalocyanine

HRID 1708357Notes

Reaction equation

HRID 1708357 reaction equation
[OH:1][Ge:2][OH:3].[CH:4]1[CH:5]=[CH:6][C:7]2[C:8](=[C:10]3[N:42]=[C:41]4[N:43]=[C:34]([C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][C:40]=54)[N:33]=[C:31]4[NH:32][C:24]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=54)=[N:23][C:21]4=[N:22][C:14]([C:15]5[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=54)=[N:13][C:12]=2[NH:11]3)[CH:9]=1.[C:44]1([CH:50]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][O:66][SiH2:67]O)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>O1CCOCC1>[C:48]1([CH:41]([C:40]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][O:66][SiH2:67][O:1][Ge:2][O:3][SiH2:67][O:66][CH2:65][CH2:64][CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH:50]([C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:49]=1.[CH:5]1[CH:4]=[CH:9][C:8]2[C:7](=[C:12]3[N:13]=[C:14]4[N:22]=[C:21]([C:20]5[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=54)[N:23]=[C:24]4[NH:32][C:31]([C:30]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=54)=[N:33][C:34]4=[N:43][C:41]([C:40]5[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=54)=[N:42][C:10]=2[NH:11]3)[CH:6]=1

Participants

4

Reactant 2

HCID 131718749DiphenylhexadecyloxysilanolHCID 178526211HCID 178526211, compound2×

Product 1

HCID 137331263Bis(diphenylhexadecyloxy-siloxy)germanium phthalocyanine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2 g (3.24 mmol) of dihydroxygermanium-phthalocyanine are boiled at reflux with 2 equivalents of diphenylhexadecyloxysilanol in 210 ml of dioxane for 39 hours. After 24 hours, 500 mg of dihydroxygermanium-phthalocyanine are added. The reaction mixture is allowed to cool and the residue is chromatographed on basic aluminium oxide (Alox B) using pure hexane and hexane/ethyl acetate (4:1) in succession as eluants. The product-containing fractions are combined and concentrated. The residue is recrystallised from pentane at -20° C., yielding blue crystals of bis(diphenylhexadecyloxy-siloxy)germanium-phthalocyanine.

Workup

  1. temperatureto cool
  2. customthe residue is chromatographed on basic aluminium oxide (Alox B)
  3. concentrationconcentrated
  4. customThe residue is recrystallised from pentane at -20° C.

Sources & evidence

ORD record
ord-119eb327c511494ca00c31d6d431e347
Source dataset
uspto-grants-1994_10
Patent number
US05358940

Reaction notes

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