Water soluble, pyran-based photochromic compounds having carboxylate functionality
OwnerJoseph Thomas Ippolitiinventor
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Abstract
The present invention provides water-soluble, pyran-based photochromic compounds characterized by improved stability when in an open, excited configuration. The advantages of the present invention are provided, at least in part, by functionalizing a pyran-based photochromic compound with carboxylate functionality in such a way that the carboxylate and/or its counter ion have sufficient mobility to engage in intermolecular and intramolecular interactions. In preferred embodiments, such a mobile carboxylate and/or counter ion provided on one side of an open pyran ring is preferably capable of complexing with functionality on the other side of the open pyran ring, greatly stabilizing the open configuration.
Claims51
An ionic photochromic compound, comprising:
- (a) a pyran moiety comprising oxygen as a ring constituent;
- (b) an aromatic moiety comprising an aromatic ring fused to the pyran moiety;
- (c) at least one heterocyclic ring moiety linked to the pyran moiety at an ortho position relative to the oxygen ring constituent;
- and
- (d) at least one carboxylate moiety linked to the heterocyclic ring moiety.
A method of making an ionic photochromic compound, comprising the steps of:
- (a) providing a reactant comprising a heterocyclic ring including a nitrogen atom as a ring constituent and comprising an aromatic moiety having an aromatic ring fused to the heterocyclic ring;
- (b) attaching a carboxyl moiety to the nitrogen atom in a manner such that the carboxyl moiety is linked to the nitrogen atom by a divalent linking group;
- (c) providing an aromatic reactant comprising an aromatic ring having substituents reactive with the product of step (b) to form a reaction product comprising a pyran ring having an oxygen atom as a ring substituent and a saturated carbon atom ortho to the oxygen atom, said substituents being reactive such that the aromatic ring of the aromatic ring is fused to the resultant pyran ring and the saturated carbon atom of the pyran ring ortho to the oxygen atom is linked to the heterocyclic ring;
- and
- (d) reacting the product of step (b) with the aromatic reactant under conditions effective to form said pyran ring, whereby the ionic photochromic compound is formed.
A method of making a photochromic compound, comprising the steps of:
- (a) providing a first reactant of the formula:
- wherein each of R1 and R2 is independently a monovalent moiety other than H or an acidic group or R1 and R2 are co-members of a cyclic ring structure;
- R3 is —CH3;
- and A3 is an aromatic moiety comprising an aromatic ring fused to the heterocyclic ring.
- (b) providing a second reactant of the formula:
- wherein X1 is a divalent linking group and Y is selected from the group consisting of a halogen atom and a tosylate group;
- (c) reacting the first reactant with the second reactant according to the following reaction scheme:
- (d) providing a third reactant of the formula:
- wherein each R independently is a monovalent moiety or, in combination with another R substituent, is a co-member of a cyclic ring structure;
- and
- (e) reacting the product of step (c) with the third reactant according to the following reaction scheme:
- whereby the photochromic compound is formed.
A method of making a photochromic compound, comprising the steps of:
- (a) providing a first reactant of the formula:
- wherein each of R1 and R2 is independently a monovalent moiety other than H or an acidic group or R1 and R2 are co-members of a cyclic ring structure;
- R3 is —CH3;
- and A3 is an aromatic moiety comprising an aromatic ring fused to the heterocyclic ring;
- (b) providing a second reactant of the formula:
- wherein X1 is a divalent linking group and Y is selected from the group consisting of a halogen atom and a tosylate group;
- (c) reacting the first reactant with the second reactant according to the following reaction scheme:
- (d) providing a third reactant of the formula:
- wherein each R independently is a monovalent moiety or, in combination with another R substituent, is a co-member of a cyclic ring structure;
- and
- (e) reacting the product of step (c) with the third reactant according to the following reaction scheme:
- whereby the photochromic compound is formed.
Dependencies are inferred from the claim text.