Substituted extensively conjugated ionic polyacetylenes
AssigneeUniversity of Lowell
InventorsAlexandra Blumstein, Sundar Subramanyam
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Abstract
A family of ionic polyacetylenes containing long sequences of conjugated double bonds in the backbone with ionic charges adjacent to or in conjugation with the backbone, and a synthetic process for preparing them, are disclosed. These polymers, which are soluble in many solvents including water, are mono- and di-substituted polyacetylenes that are extensively conjugated. The charge density and geometry of charge distribution depends on the number and nature of the substituents.
Claims28
A method of preparing a conjugated polyacetylene comprising reacting a compound containing a quaternizable heteroatom with a compound that functions as a quaternizing agent, wherein one of the compounds is an acetylenic monomer having a carbon-carbon triple bond, under conditions sufficient to form a quaternized acetylene monomer having an acetylenic triple bond that is directly attached to the heteroatom or that is conjugated with the heteroatom through a sequence of conjugated carbon-carbon double bonds, whereby the carbon-carbon triple bond on the quaternized acetylene monomer spontaneously polymerizes to form the conjugated polyacetylene.
A method for preparing conjugated polyacetylene comprising:
- a) reacting an acetylene monomer having the formula:
- R--C.dbd.C--X
- wherein R is selected from the group consisting of:
- H, alkyl, alkoxy, alkylthio, trialkylsilyl, trialkyloxysilyl, aryl, aryloxy, arylthio, triarylsilyl, triaryloxysilyl, ester and thioester groups;
- and X is an atom or group of atoms capable of forming an anion, with a quaternizing agent having the formula:
- R'--Y
- where R' is an alkyl or aryl group and Y is a heteroatom which is part of a cyclic, heterocyclic or heterocyclicaromatic compound which is susceptible to quaternization, under conditions sufficient for quaternization of the heteroatom to occur, thereby forming a quaternized acetylene intermediate;
- and
- b) maintaining the reaction under conditions sufficient for spontaneous polymerization of the quaternized acetylene intermediate to occur.
A method for preparing a conjugated polyacetylene comprising:
- a) reacting an acetylene monomer having a conjugated nitrogen atom susceptible to quaternization with a quaternizing agent having the formula:
- R'--X
- wherein R' is an alkyl or aryl group and X is an atom or a group of atoms capable of forming an anion, under conditions sufficient for quaternization of the nitrogen atom to occur thereby forming a quaternized intermediate;
- and
- b) maintaining the reaction under conditions sufficient for spontaneous polymerization of the quaternized intermediate to occur.
A method for preparing a conjugated polyacetylene comprising:
- a) reacting 1,2-bis-4'-pyridylacetylene with one or two equivalents of a quaternizing agent having the formula:
- R--X
- wherein R is an alkyl group, an aryl group or a macromolecule and X is an atom or a group of atoms capable of forming an anion, under conditions sufficient for quaternization of the nitrogen atom to occur thereby forming a quaternized intermediate;
- and
- b) maintaining the reaction under conditions sufficient for spontaneous polymerization of the quaternized intermediate to occur.
A method for preparing conjugated polyacetylenes comprising:
- a) reacting an acetylene monomer having a nitrogen, phosphorous or arsenic atom susceptible to quaternization with a metal halide having the formula:
- M.sub.a --X.sub.b
- wherein M is a metal atom, X is an atom or a group of atoms capable of forming an anion, and a and b are integers representing the number of each atoms or groups of atoms in the formula;
- under conditions sufficient for quaternization of the nitrogen atom to occur, thereby forming a quaternized intermediate;
- and
- b) maintaining the reaction under conditions sufficient for spontaneous polymerization of the quaternized intermediate to occur.
Dependencies are inferred from the claim text.