Pentafluorosulfanyl phthalocyanine derivatives and intermediates thereof

1. A phthalocyanine derivative of the following general formula (1):

(wherein M is a hydrogen atom, a metal element, a metalloid element, a metal oxide, a metalloid oxide, a metal hydroxide, a metalloid hydroxide, a metal halide, or a metalloid halide, and

R is each independently a hydrogen atom, an alkyloxy group, an aryloxy group, an alkyl sulfide group, an aryl sulfide group, or a trifluoromethyl group).

2. The phthalocyanine derivative according to claim 1 , wherein R is a hydrogen atom.

3. The phthalocyanine derivative according to claim 1 , wherein R is an alkyloxy group, an aryloxy group, an alkyl sulfide group, an aryl sulfide group, or a trifluoromethyl group.

4. The phthalocyanine derivative according to claim 1 , wherein R is a trifluoromethyl group, a phenoxy group, or a phenyl sulfide group.

5. A halogen-containing pentafluorosulfanyl benzene derivative of the following general formula (2):

(wherein Hal is a halogen atom, and X is a hydrogen atom, a halogen atom, or a cyano group).

6. A pentafluorosulfanyl phthalonitrile derivative of the following general formula (3):

(wherein R is a hydrogen atom, an alkyloxy group, an aryloxy group, an alkyl sulfide group, an aryl sulfide group, or a trifluoromethyl group).

7. A process for preparing the phthalocyanine derivative according to claim 1 , the process comprising the steps of:

(A) providing a pentafluorosulfanyl phthalonitrile derivative of the following general formula (3):

(wherein R is a hydrogen atom, an alkyloxy group, an aryloxy group, an alkyl sulfide group, an aryl sulfide group, or a trifluoromethyl group); and

(B) heating the pentafluorosulfanyl phthalonitrile derivative together with hydrogen, a metal, a metalloid, a metal oxide, a metalloid oxide, a metal hydroxide, a metalloid hydroxide, a metal halide, or a metalloid halide.

8. The process according to claim 7 , wherein R in the pentafluorosulfanyl phthalonitrile derivative of the general formula (3) is selected from the group consisting of a hydrogen atom, an alkyl sulfide group, an aryl sulfide group, and a trifluoromethyl group;

wherein the step (A) is a step of providing the pentafluorosulfanyl phthalonitrile derivative of the general formula (3), by following a step of converting a halogen-containing pentafluorosulfanyl benzene derivative of the following general formula (2):

(wherein Hal is a halogen atom, and X is a hydrogen atom, a halogen atom, or a cyano group) into the pentafluorosulfanyl phthalonitrile derivative the general formula (3), wherein when X is H, Hal in the derivative of general formula (2) is converted into CN group by a cyanide;

when X is CN, Hal in the derivative of general formula (2) is converted into a trifluoromethyl group by the Yagupolskii reagent, and to an aryloxy group by phenols, or to an arylsulfide group by thiophenols; and

when X is Hal, one of Hal in the derivative of general formula (2) is converted into CN by cyanide and the other Hal in the derivative of general formula (2) is converted into a trifluoromethyl group by the Yagupolskii reagent, and to an aryloxy group by phenols, or to an arylsulfide group by thiophenols.

9. A process for preparing the phthalocyanine derivative according to claim 2 , the process comprising the steps of:

(A1) converting Hal in a halogen-containing pentafluorosulfanyl benzene derivative of the following general formula (2a):

(wherein Hal is a halogen atom)

into a cyano group, to thereby provide a pentafluorosulfanyl phthalonitrile derivative of the following general formula (3a):

and

(B) heating the pentafluorosulfanyl phthalonitrile derivative together with hydrogen, a metal, a metalloid, a metal oxide, a metalloid oxide, a metal hydroxide, a metalloid hydroxide, a metal halide, or a metalloid halide.

10. A process for preparing the phthalocyanine derivative according to claim 3 , the process comprising the steps of:

(A2) converting one Hal and the other Hal in a halogen-containing pentafluorosulfanyl benzene derivative of the following general formula (2b):

(wherein Hal is a halogen atom)

into a cyano group and R′, respectively, to thereby provide a pentafluorosulfanyl phthalonitrile derivative of the following general formula (3b):

(wherein R′ is alkyloxy group, an aryloxy group, an alkyl sulfide group, an aryl sulfide group, or a trifluoromethyl group); and

(B) heating the pentafluorosulfanyl phthalonitrile derivative together with hydrogen, a metal, a metalloid, a metal oxide, a metalloid oxide, a metal hydroxide, a metalloid hydroxide, a metal halide, or a metalloid halide.

11. A process for preparing the phthalocyanine derivative according to claim 3 , the process comprising the steps of:

(A3) converting Hal in a halogen-containing pentafluorosulfanyl benzene derivative of the following general formula (2c):

(wherein Hal is a halogen atom)

into R′, to thereby provide a pentafluorosulfanyl phthalonitrile derivative of the following general formula (3c):

(wherein R′ is an alkyloxy group, an aryloxy group, an alkyl sulfide group, an aryl sulfide group, or a trifluoromethyl group); and

(B) heating the pentafluorosulfanyl phthalonitrile derivative together with hydrogen, a metal, a metalloid, a metal oxide, a metalloid oxide, a metal hydroxide, a metalloid hydroxide, a metal halide, or a metalloid halide.