Eyewear including catechol functionalized boron pyrromethene dye for neutralizing laser threat
View Patent ↗The embodiments described herein generally relate to compositions and articles including dye compounds having desirable optical properties, and related methods. In some cases, the compositions and articles may possess advantageous optical properties, including various degrees of absorbance, emission, and/or transmission at particular wavelengths or ranges of wavelength. Embodiments described herein may be useful as optical filters in protective eyewear applications.
1. An article, comprising: an optical filter including a substantially optically transparent polymer; and a boron pyrromethene compound associated with the polymer, wherein the optical filter has a quantum yield of fluorescence of about 5% or less upon exposure to electromagnetic radiation between about 300 nm and about 600 nm, wherein the optical filter is included in eyewear, and is selected from the group consisting of a lens, goggle, eyeglasses, and visor.
2. The article according to claim 1 , wherein the boron pyrromethene compound is dispersed on or within the polymer formed as a coating on the optical filter.
3. The article according to claim 1 , wherein the boron pyrromethene compound is formed as a coating on the optical filter.
4. The article according to claim 1 , wherein the boron pyrromethene compound has a maximum absorption peak between about 400 nm and about 800 nm.
5. The article according to claim 4 , wherein the boron pyrromethene compound has a maximum absorption peak at about 532 nm.
6. The article according to claim 1 , wherein the boron pyrromethene compound comprises an electron-donating group.
7. The article according to claim 1 , wherein the boron pyrromethene compound comprises a catechol group.
8. The article according to claim 1 , wherein the boron pyrromethene compound has the following structure,
wherein:
each R 1 -R 6 can be the same or different and each is hydrogen, halo, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, OR′, N(R′) 2 , or SR′, any of which is optionally substituted; and any two of R 1 -R 6 can be joined to form a ring, optionally substituted;
X is N or CR 7 , wherein R 7 is hydrogen, halo, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, OR′, N(R′) 2 , or SR′, any of which is optionally substituted;
Y 1 and Y 2 can be the same or different and each is halo, OR′, N(R′) 2 , or SR′, any of which is optionally substituted; or Y 1 and Y 2 are joined to form a ring, optionally substituted; and
R′ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, or heteroaryl, any of which is optionally substituted.
9. The article according to claim 8 , wherein Y 1 and Y 2 are joined to form a catechol group or a bisnaphthol group, any of which is optionally substituted.
10. The article according to claim 1 , wherein the substantially optically transparent polymer is polycarbonate.
11. The article according to claim 1 , wherein the boron pyrromethene compound having the following structure,
wherein:
each R 1 -R 6 can be the same or different and each is hydrogen, halo, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, OR′, N(R′) 2 , or SR′, any of which is optionally substituted; and any two of R 1 -R 6 can be joined to form a ring, optionally substituted;
R 7 is hydrogen, halo, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, OR′, N(R′) 2 , or SR′, any of which is optionally substituted;
each R 8 -R 11 can be the same or different and each is hydrogen, halo, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, OR′, N(R′) 2 , or SR′, any of which is optionally substituted; and any two of R 8 -R 11 can be joined to form a ring, optionally substituted; and
R′ is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, or heteroaryl, any of which is optionally substituted.
12. The article according to claim 11 , wherein the compound has the following structure,
13. The article according to claim 11 , wherein the compound has the following structure,
14. The article according to claim 11 , wherein the compound has the following structure,
15. The article according to claim 11 , wherein the compound has the following structure,
16. The article according to claim 11 , wherein the compound has the following structure,
17. The article according to claim 11 , wherein the compound has the following structure,
18. An article, comprising: an optical filter including a substantially optically transparent polymer and a boron pyrromethene compound associated with the polymer, wherein, when the article has an optical density of about 4 at an absorbance wavelength, the article has a scotopic luminous transmittance (SLT) from about 10% to about 50%, wherein the optical filter is included in eyewear, and is selected from the group consisting of a lens, goggle, eyeglasses, and visor.