Aryloxy-phthalocyanines of group IV metals

A compound of a general molecular structure (II):

• wherein M is silicon, tin, or a combination thereof;
• wherein “n” is an integer equal to or greater than 0;
• wherein each R1 independently is a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof;
• and
• wherein R2 and R3 are the same or different and are a halogen, oxygen, sulfur, nitrogen, or an aryloxy containing group and at least one or the R2 and R3 is a meta-substituted aryloxy containing group having from 7 to about 10 carbon atoms.

A method for preparing a compound of the general molecular structure (I):

• wherein M is silicon, germanium, tin, or a combination thereof;
• wherein “n”is an integer equal to or greater than 0;
• wherein each R1 independently is a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof;
• wherein R2 is a substituted aryl containing group having about 7 to about 22 carbon atoms, the method, comprising the steps of:
• a) providing a compound having a halogen-metal bond containing R1 substituted phthalocyanines precursor, wherein the halogen is chlorine, bromine, iodine, fluorine, or a combination thereof;
• and wherein each R1 independently is a straight chain alkylgroup, a branched alkyl group, a cycloalkyl group, and alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof;
• b) providing a reactant having a meta-substituted aryl (—R2 )or a meta-substituted arylalcohol group (OH—R2 ), wherein R2 comprises from 7 to about 22 carbon atoms, and
• c)reacting the compound having a halogen-metal bond containing phthalocyanines precursor and the reactant in the presence of an organic solvent under conditions effective to form the compound of the general molecular structure (I), wherein the compound of the general molecular structure (I) is non-soluble, negiligibly soluble, partially soluble in an organic solvent, or at least partially soluble in an organic solvent.

A method for preparing a compound of the general molecular structure (II):

• wherein M is silicon, germanium, -tin, or a combination thereof;
• wherein “n”is an integer equal to or greater than 0;
• wherein each R1 independently is a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof;
• and
• wherein R2 and R3 are the sme or different and are a halogen, oxygen, sulfur, nitrogen, or an aryloxy containing group and at least one of the R2 and R3 is a substituted aryloxy containing group having about 7 to about 22 carbon atoms,
• the method, comprising the steps of:
• a) providing a compound having a halogen-metal bond containing R1 substituted phthalocyanines precursor, wherein the halogen is chlorine, bromine, iodine, fluorine, or a combination thereof, and wherein each R1 independently has a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, and alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydeogen, a halogen, or a combination thereof;
• b) providing a reactant having R2 and/or R3 moieties, wherein R2 and R3 are the same or different and have a halogen, oxygen, sulfur, nitrogen, or an aryloxy containing group, and at least one of the R2 and R3 is aryloxy containing group having from 7 to about 10 carbon atoms;
• and
• (c)reacting the compound having a halogen-metal bond containing phthalocyanines precursor and the reactant in the presence of an organic solvent under conditions effective to form the compound of the general molecular structure (II), wherein the compound of the general molecular structure (II) is non-soluble, negiligibly soluble, partially soluble in an organic solvent, or at least partially soluble in an organic solvent.

A compound of a general structure (I):

• wherein M is silicon, germanium, tin, or a combination thereof;
• wherein “n”is an integer equal to or greater than 0;
• wherein each R1 independently is a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof;
• wherein R2 is a substituted aryl containing group having about 7 to about 22 carbon atoms, and includes a halogen selected from the group consisting essentially of fluorine, chlorine, bromine, iodine, and a combination thereof.

A compound of a general molecular structure (II):

• wherein M is silicon, germanium, tin, or a combination thereof;
• wherein “n”is an integer equal to or greater than 0;
• wherein each R1 independently is a straight chain alkyl group, a branched alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, heterocyclic group, a monocyclic aromatic group, a polycyclic aromatic group, an aryl group, an alkylaryl group, an arylalkyl group, an akylene group, a hydrogen, a halogen, or a combination thereof;
• and
• wherein R2 and R3 are the same or different and are a halogen, oxygen, sulfur, nitrogen, or an aryloxy containing group and at least one of the R2 and R3 includes a substituted aryloxy containing group having about 7 to about 22 carbon atoms, and a halogen selected from the group consisting essentially of fluorine, chlorine, bromine, iodine, and a combination thereof.