Patent ID: 7790068
Filing Date: 2010-09-07
Classification: C07D

Abstract:
1. A photochromic compound which is a [1,3]oxazine compound substituted at one or more positions, wherein the unsubstituted [1,3]oxazine compound is described as having a structure with fused indoline and benzooxazine fragments such that they are fused along (i) the bond connecting positions 1 and 2 of the indoline fragment and (ii) the bond connecting positions 2 and 3 of the benzooxazine fragment, and further substituted by an electron withdrawing group for a hydrogen attached at any position of the phenyl ring of the benzooxazine fragment, wherein said [1,3]oxazine compound has a substituted structure as shown in Formula I: wherein R 1 , R 4 , and R 5 are selected to adjust (i) excitation wavelength for cleavage of the [C—O] bond in said compound to produce a phenolate derivative by the ring cleavage and (ii) absorbance wavelength of the phenolate derivative and R 2 and R 3 are selected to adjust the [1,3]oxazine compound's rate of coloration and/or decoloration, wherein said R 2 and R 3 are different; wherein said R 1 is selected from the group consisting of hydrogen, hydroxyl, C1-C4 alkyls, C5-C6 cycloalkyls, substituted C1-C4 alkyls, substituted C5-C6 cycloalkyls, C5-C6 aryls, substituted C5-C6 aryls, C5-C6 heterocycles, and substituted C5-C6 heterocycles; wherein said R 2 is selected from the group consisting of hydrogen, hydroxyl, C1-C4 alkyls, C5-C6 cycloalkyls, substituted C1-C4 alkyls, substituted C5-C6 cycloalkyls, C5-C6 aryls, substituted C5-C6 aryls, C5-C6 heterocycles, and substituted C5-C6 heterocycles; wherein said R 3 is selected from the group consisting of hydrogen, hydroxyl, C1-C4 alkyls, C5-C6 cycloalkyls, substituted C1-C4 alkyls, substituted C5-C6 cycloalkyls, C5-C6 aryls, substituted C5-C6 aryls, C5-C6 heterocycles, and substituted C5-C6 heterocycles; wherein said R 4 is selected from the group consisting of hydrogen, hydroxyl, C1-C4 alkyls, C5-C6 cycloalkyls, substituted C1-C4 alkyls, substituted C5-C6 cycloalkyls, C5-C6 aryls, substituted C5-C6 aryls, C5-C6 heterocycles, and substituted C5-C6 heterocycles; wherein said R 5 is a nitrogen-containing group or any other electron withdrawing substituent; wherein a light excitation induces cleavage of a [C—O] bond in the oxazine ring of said compound to produce a phenolate derivative by ring cleavage; wherein said compound switches to said phenolate derivative in 250 ns or less; wherein isomerization between said compound and said phenolate derivative is thermally reversible without said light.