Photochromic compounds based on ring opening and closing of an [1,3]oxazine compound
US8252209B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Aug 6, 2010 |
| Grant date | Aug 28, 2012 |
| Priority date | — |
| Expiry date | Aug 6, 2030 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D498/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
We have designed a molecular switch based on the photoinduced opening and thermal closing of a [1,3]oxazine ring. A substituted [1,3]oxazine compound described as having a general (i.e., unsubstituted) structure with fused indoline and benzooxazine fragments such that they share a common bond in the [1,3]oxazine compound: (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. Irradiation by light of suitable wavelength and intensity of this photochromic compound induces cleavage of a [C—O] bond of the [1,3]oxazine ring to form a phenolate chromophore. The photogenerated (e.g., colored) isomer may revert thermally to the starting (e.g., colorless) oxazine. Alternatively, the switch may be between isomers of the compound that absorb at different wavelengths. Reversible coloration of silica or polymeric materials and switching optical signals may involve many cycles of interconversion between different colored states. A colorless/colored state may be maintained by constant irradiation or chemical trapping.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.