Novel pyrrole monomers and polymers prepared therefrom

Claim 2

A pyrrole having the general formula wherein m is an integer of from 1 to 18 and R is hydrogen, an alkyl group containing from 1 to 6 carbon atoms, an aryl group, or is the group where m is as above defined.

Claim 3

A pyrrole as claimed in claim 1 wherein R is a hydrogen atom

Claim 4

3-Octanoylpyrrole.

Claim 5

3-Octanoylpyrrole.

Claim 6

3-Dodecanoylpyrrole.

Claim 7

3-Dodecanoylpyrrole.

Claim 8

3-Octadecanoylpyrrole.

Claim 9

3-Octadecanoylpyrrole.

Claim 10

A process for the preparation of a pyrrole as claimed in claim 1, which process comprises reacting a pyrrole derivative of the formula where R is as defined in claim 1 and V is a protecting group, preferably a p-toluenesulphonyl group, with an acid chloride of the formula R I COCI where R 1 is the group -(CH 2 ) m CH 3 where m is as defined in claim 1, in the presence of an aluminium chloride catalyst to form the compound and subsequently removing the protecting group therefrom to give the compound of the formula

Claim 11

A polypyrrole derivative which comprises repeating units of the general formula where R and m are as defined in claim 1 and counterions of the formula X, where X is chloride, bromide, sulphate, bisulphate, nitrate, tetrafluoroborate, alkylsulphonate, arylsulphonate, arenecarboxylate, alkylcarboxylate, arenedicarboxylate, polystyrenesulphonate, polyacrylate, cellulose sulphonate, cellulose sulphate, anthracene sulphonate, H2PO 3 , H2PC 4 , PF 6 , SbF 6 , AsF 6 or a perfluorinated polyanion.

Claim 12

A polypyrrole derivative as claimed in claim 7 wherein the counterion is PF6" .

Claim 13

A process for the preparation of a polypyrrole derivative as claimed in claim 7 or claim 8 which process comprises subjecting a pyrrole monomer as claimed in claim 1 in a non-aqueous solvent to electrochemical oxidation at an electrode potential which is at least as electropositive as the oxidation potential of the pyrrole monomer.

Claim 14

A process as claimed in claim 10 wherein the solvent is acetonitrile, dichloromethane, chloroform, nitromethane, nitrobenzene, propylene carbonate, N-methylpyrrolidone, sulpholane, dimethylformamide, dimethylsulphoxide or trichlorobenzene, or a mixture of two or more thereof.

Claim 15

A process as claimed in claim 9 or claim 10 wherein the electrochemical oxidation is carried out in an electrolyte which provides the counterion X, where X is as defined in claim 7.

Claim 16

A copolymer of a pyrrole derivative as claimed in any one of claims 1 to 6 with another monomer which is polymerisable therewith.

Claim 17

A copolymer as claimed in claim 12 wherein the other monomer is pyrrole.

Claim 18

The use of a polymer as claimed in claim 7 or claim 8 in a photovoltaic cell, preferably a solar cell.

Claim 19

A process for the preparation of a pyrrole having the general formula wherein m is an integer of from 1 to 18 and R is hydrogen, an alkyl group containing from 1 to 6 carbon atoms, an aryl group, or is the group where m is as above defined, which process comprises reacting a pyrrole derivative of the formula where R is as above defined and V is a protecting group, with an acid chloride of the formula R'COCI where R 1 is the group -(CH 2 ) m CH 3 where m is as defined above in the presence of an aluminium chloride catalyst to form the compound and subsequently removing the protecting group therefrom to give the compound of the formula

Claim 20

A process for the preparation of a pyrrole having the general formula wherein m is an integer of from 1 to 18 and R is hydrogen, an alkyl group containing from 1 to 6 carbon atoms, an aryl group, or is the group where m is as above defined, which process comprises reacting a pyrrole derivative of the formula where R is as above defined and V is a protecting group, with an acid chloride of the formula R'COCI where R 1 is the group -(CH 2 ) m CH 3 where m is as defined above in the presence of an aluminium chloride catalyst to form the compound and subsequently removing the protecting group therefrom to give the compound of the formula

Claim 21

A process as claimed in claim 1 wherein the protecting group is a p-toluenesulphonyl group.

Claim 22

A process for the preparation of a polypyrrole derivative having repeating units of the general formula where R and m are as defined in claim 1 and counterions of the formula X, where X is chloride, bromide, sulphate, bisulphate, nitrate, tetrafluoroborate, alkylsulphonate, arylsulphonate, arenecarboxylate, alkylcarboxylate, arenedicarboxylate, polystyrenesulphonate, polyacrylate, cellulose sulphonate, cellulose sulphate, anthracene sulphonate, H2PO 3 , H2PO 4 , PF 6 , SbF 6 , AsF 6 or a perfluorinated polyanion, which process comprises subjecting a pyrrole monomer as defined in claim 1 in a non-aqueous solvent to electrochemical oxidation at an electrode potential which is at least as electropositive as the oxidation potential of the pyrrole monomer.

Claim 23

A process as claimed in claim 3 wherein the solvent is acetonitrile, dichloromethane, chloroform, nitromethane, nitrobenzene, propylene carbonate, N-methylpyrrolidone, sulpholane, dimethylformamide, dimethylsulphoxide or trichlorobenzene, or a mixture of two or more thereof.

Claim 24

A process as claimed in claim 3 or claim 4 wherein the electrochemical oxidation is carried out in an electrolyte which provides the counterion X.

Claim 25

The use of a polymer as defined in claim 3 in a photovoltaic cell, preferably a solar cell.