Abstract
A convenient preparation of phthalocyanines from phthalonitriles
was accomplished by treatment with metal salts and hexamethyldisilazane
(HMDS) in DMF at 100 °C. This reaction provides
a new preparative method under mild conditions for phthalocyanines
having a variety of metals and substituted phthalocyanines as well
as Zn-naphthalocyanine.
Key words
phthalocyanine - naphthalocyanine - phthalonitrile - hexamethyldisilazane - dye
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Representative
Procedure : A mixture of phthalonitrile (107 mg, 0.84 mmol),
HMDS (0.35 mL, 1.66 mmol), ZnBr2 (50 mg, 0.22 mmol),
and DMF (0.21 mL) was heated at 100 °C under Ar
atmosphere. The mixture was separated into two phases. After heating
for 10 h, the reaction mixture was subjected to evaporation under
reduced pressure. The resultant solid was washed successively with
MeOH (50 mL) and with water (50 mL). The obtained crude product was
further purified by extraction with chloroform (50 mL) using Soxhlet’s
extractor, and dried under reduced pressure, affording Zn-phthalocyanine 7a (91 mg) in 78% yield. Anal. Found:
C, 66.21; H, 2.88; N, 19.59. Calcd: C, 66.50; H, 2.79; N, 19.39.
IR (KBr):1608, 1486, 1456, 1412, 1331, 1285, 1167, 1118, 1090, 1061,
887, 778, 752, 727 cm-1 . TOF MS (MALDI):
576.2 (M+ ). All the compounds obtained are known
and in agreement with the spectral and analytical data.
