Method and compositions providing enhanced chemiluminescence from 1,2-dioxetanes

Claim 1

A method for generating light which comprises: (a) providing in a setting where the light is to be produced a fluorescent compound dispersed in or on one of a surfactant, a micelle, liposome, reversed micelle, microemulsion film, including a monolayer or a polymer which brings the fluorescent compound into a closely spaced relationship with and in admixture with a 1,2-dioxetane which is stable in the setting where light is to be produced of the formula ##STR32## wherein ArOX represents an aryl group substituted with an X-oxy group which forms an oxide intermediate 1,2-dioxetane compound when triggered by removing X with an activating agent so that the intermediate 1,2-dioxetane compound decomposes and releases electronic energy to form light and two carbonyl containing compounds of the formula ##STR33## wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate 1,2-dioxetane and wherein A are passive organic groups which allow the light to be produced by the 1,2-dioxetane when X is removed; and (b) triggering the stable 1,2dioxetane with the activating agent wherein the fluorescent compound accepts the electronic energy generated upon decomposition of the oxide intermediate light than is produced by the triggering of the dioxetane alone.

Claim 2

A method for generating light which comprises: (a) providing in a setting where the light is to be produced a fluorescent compound dispersed in or on one of a surfactant, a micelle, liposome, reversed micelle, microemulsion film, including a monolayer or a polymer which brings the fluorescent compound into a closely spaced relationship with and in admixture with a 1,2-dioxetane which is stable in the setting where light is to be produced of the formula ##STR32## wherein ArOX represents an aryl group substituted with an X-oxy group which forms an oxide intermediate 1,2-dioxetane compound when triggered by removing X with an activating agent so that the intermediate 1,2-dioxetane compound decomposes and releases electronic energy to form light and two carbonyl containing compounds of the formula ##STR33## wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate 1,2-dioxetane and wherein A are passive organic groups which allow the light to be produced by the 1,2-dioxetane when X is removed; and (b) triggering the stable 1,2dioxetane with the activating agent wherein the fluorescent compound accepts the electronic energy generated upon decomposition of the oxide intermediate light than is produced by the triggering of the dioxetane alone.

Claim 3

A method for generating light which comprises: (a) providing in a setting where the light is to be produced a fluorescent compound dispersed in or on one of a surfactant, a micelle, liposome, reversed micelle, microemulsion, film, including a monolayer or a polymer which brings the fluorescent compound into a closely spaced relationship with and in admixture with a 1,2-dioxetane compound which is stable in the setting where the light is to be produced of the formula ##STR34## wherein R 1 and R 2 together and R 3 and R 4 together can be joined as spirofused cycloalkylene which can obtain hereto atoms selected from the group consisting of N, S, O and P in addition to carbon and aryl rings, wherein at least one of R 1 and R 2 or R 3 and R 4 is an aryl group substituted with an X-oxy group which forms an oxide intermediate 1,2dioxetane compound when triggered by removing X with an activating agent selected from acids, bases, salts, enzymes, inorganic and organic catalysts and other electron donors so that the oxide intermediate 1,2-dioxetane compound decomposes and releases electronic energy to form light and two carbonyl containing compounds of the formula: ##STR35## wherein those of R 1 , R 2 , R 3 or R 4 which are unsubstituted by an X-oxy group are carbon and hereto atom containing organic groups which provide stability for the stable 1,2-dioxetane compound and wherein X is a chemically labile group which is removed by the activating agent to form the oxide intermediate 1,2-dioxetane; and (b) triggering the stable 1,2-dioxetane with the activating agent to remove X wherein the fluorescent compound accepts the electronic energy generated upon decomposition of the oxide intermediate 1,2-dioxetane compound and produces a more intense light than is produced by the triggering of the dioxetane alone.

Claim 4

A method for generating light which comprises: (a) providing in a setting where the light is to be produced a fluorescent compound dispersed in or on one of a surfactant, a micelle, liposome, reversed micelle, microemulsion, film, including a monolayer or a polymer which brings the fluorescent compound into a closely spaced relationship with and in admixture with a 1,2-dioxetane compound which is stable in the setting where the light is to be produced of the formula ##STR34## wherein R 1 and R 2 together and R 3 and R 4 together can be joined as spirofused cycloalkylene which can obtain hereto atoms selected from the group consisting of N, S, O and P in addition to carbon and aryl rings, wherein at least one of R 1 and R 2 or R 3 and R 4 is an aryl group substituted with an X-oxy group which forms an oxide intermediate 1,2dioxetane compound when triggered by removing X with an activating agent selected from acids, bases, salts, enzymes, inorganic and organic catalysts and other electron donors so that the oxide intermediate 1,2-dioxetane compound decomposes and releases electronic energy to form light and two carbonyl containing compounds of the formula: ##STR35## wherein those of R 1 , R 2 , R 3 or R 4 which are unsubstituted by an X-oxy group are carbon and hereto atom containing organic groups which provide stability for the stable 1,2-dioxetane compound and wherein X is a chemically labile group which is removed by the activating agent to form the oxide intermediate 1,2-dioxetane; and (b) triggering the stable 1,2-dioxetane with the activating agent to remove X wherein the fluorescent compound accepts the electronic energy generated upon decomposition of the oxide intermediate 1,2-dioxetane compound and produces a more intense light than is produced by the triggering of the dioxetane alone.

Claim 5

A method for generating light which comprises: (a) providing in a setting where the light is to be produced a fluorescent compound dispersed in or on one of a surfactant, a micelle, liposome, reversed micelle, microemulsion, film, including a monolayer or a polymer which brings the fluorescent compound and the dioxetane into a closely spaced relationship with and in admixture with a dioxetane compound which is stable in the setting where the light is to be produced of the formula: ##STR36## wherein R 1 is selected from alkyl, alkoxy, aryloxy dialkylamino, trialkyl or aryl silyloxy and aryl groups including spirofused aryl groups joined with R 2 , wherein R 2 is an aryl group which can include R 1 and is substituted with an X-oxy group which forms an oxide intermediate 1,2-dioxetane compound when triggered by removing X with an activating agent selected from acids, bases, salts, enzymes, inorganic and organic catalysts and other electron donors so that the oxide intermediate 1,2-dioxetane compound decomposes and releases electronic energy to form light and two carbonyl containing compounds of the formula: ##STR37## wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate 1,2-dioxetane compound and wherein R 3 and R 4 are selected from aryl, heteroalkyl and alkyl groups which can be joined together as spirofused polycyclic alkyl and polycyclic aryl groups; and (b) triggering the stable 1,2-dioxetane with the activating agent to remove X wherein the fluorescent compound accepts the electronic energy generated upon decomposition of the oxide intermediate 1,2-dioxetane compound and produces a more intense light than is produced by the triggering of the dioxetane alone.

Claim 6

A method for generating light which comprises: (a) providing in a setting where the light is to be produced a fluorescent compound dispersed in or on one of a surfactant, a micelle, liposome, reversed micelle, microemulsion, film, including a monolayer or a polymer which brings the fluorescent compound and the dioxetane into a closely spaced relationship with and in admixture with a dioxetane compound which is stable in the setting where the light is to be produced of the formula: ##STR36## wherein R 1 is selected from alkyl, alkoxy, aryloxy dialkylamino, trialkyl or aryl silyloxy and aryl groups including spirofused aryl groups joined with R 2 , wherein R 2 is an aryl group which can include R 1 and is substituted with an X-oxy group which forms an oxide intermediate 1,2-dioxetane compound when triggered by removing X with an activating agent selected from acids, bases, salts, enzymes, inorganic and organic catalysts and other electron donors so that the oxide intermediate 1,2-dioxetane compound decomposes and releases electronic energy to form light and two carbonyl containing compounds of the formula: ##STR37## wherein X is a chemically labile group which is removed by the activating agent to form the unstable oxide intermediate 1,2-dioxetane compound and wherein R 3 and R 4 are selected from aryl, heteroalkyl and alkyl groups which can be joined together as spirofused polycyclic alkyl and polycyclic aryl groups; and (b) triggering the stable 1,2-dioxetane with the activating agent to remove X wherein the fluorescent compound accepts the electronic energy generated upon decomposition of the oxide intermediate 1,2-dioxetane compound and produces a more intense light than is produced by the triggering of the dioxetane alone.