Photochromic compounds and compositions

Patent metadata

Field	Value
Publication number	US-9034219-B2
Application number	US-201113313178-A
Country	US
Kind code	B2
Filing date	Dec 7, 2011
Priority date	Dec 16, 2010
Publication date	May 19, 2015
Grant date	May 19, 2015

Abstract

Described herein are compounds generally comprising an indeno[2′,3′:3,4]naptho[1,2-b]pyran structure. Such compounds may be useful for their photochromic properties, and be used in certain photochromic compositions. Such compositions may further comprise other photochromic compositions and/or materials. Additionally, such compounds and/or compositions may be suitable for preparing certain photochromic articles. Also described herein are methods for preparing certain photochromic compounds, compositions, and articles.

First claim

We claim:

1. A compound of Formula II,

wherein,
R 1 is selected from bromo, perhaloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, aryl, heteroaryl, perhaloalkoxy, carboxy, amino, optionally substituted amino, cyano, nitro, sulfonyl, sulfonato, alkylcarbonyl, and alkoxycarbonyl;
R 5 for each occurrence, is independently selected from chiral or achiral groups selected from formyl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, aminocarbonyloxy, alkoxycarbonylamino, boronic acid, boronic acid esters, alkyl, alkenyl, alkynyl, halogen, cycloalkyl, aryl, heteroaryl, alkoxy, heteroalkyl, heterocycloalkyl, amino, and perhaloalkyl;
m is an integer from 0 to 3;
n is an integer from 0 to 4;
R 6 and R 7 are each independently selected from hydrogen, hydroxy and chiral or achiral groups selected from optionally substituted heteroalkyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted heterocycloalkyl, halogen, optionally substituted amino, carboxy, alkylcarbonyl, alkoxycarbonyl, optionally substituted alkoxy, and aminocarbonyl, or R 6 and R 7 may be taken together with any intervening atoms to form a group selected from oxo, optionally substituted cycloalkyl, and optionally substituted heterocycloalkyl; and
B and B′ are each independently selected from hydrogen, halogen, and chiral or achiral groups selected from metallocenyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted heteroalkyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocycloalkyl, and optionally substituted cycloalkyl, or wherein B and B′ are taken together with any intervening atoms to form a group selected from optionally substituted cycloalkyl and optionally substituted heterocycloalkyl.

2. The compound of claim 1 , wherein:
R 1 is selected from optionally substituted C 2 -C 6 alkenyl, optionally substituted C 2 -C 6 alkynyl, phenyl, C 1 -C 6 perhaloalkoxy, C 1 -C 6 perhaloalkyl, bromo, cyano, nitro, C 1 -C 6 alkylcarbonyl, and C 1 -C 6 alkoxycarbonyl;
R 5 for each occurrence, is independently selected from formyl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkyl, boronic acid ester, halogen, cycloalkyl, aryl, alkoxy, heteroalkyl, heterocycloalkyl, amino, and perhaloalkyl;
m and n are each independently an integer selected from 0 to 2;
R 6 and R 7 are each independently selected from hydrogen, hydroxy, and chiral and achiral groups selected from optionally substituted heteroalkyl, optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, halogen, optionally substituted amino, carboxy, alkylcarbonyl, alkoxycarbonyl, optionally substituted alkoxy, and aminocarbonyl or R 6 and R 7 may be taken together with anyintervening atoms to form a group selected from oxo, optionally substituted cycloalkyl and optionally substituted heterocycloalkyl; and
B and B′ are each independently selected from hydrogen, halogen, chiral or achiral groups selected from optionally substituted alkyl, optionally substituted alkenyl, optionally substituted heteroalkyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heteroaryl, and optionally substituted cycloalkyl, or wherein B and B′ are taken together with any intervening atoms to form a group selected from optionally substituted cycloalkyl and optionally substituted heterocycloalkyl.

3. The compound of claim 2 , wherein:
R 1 is selected from optionally substituted C 2 -C 4 alkenyl, optionally substituted C 2 -C 4 alkynyl, phenyl, C 1 -C 4 perhaloalkoxy, C 1 -C 4 perhaloalkyl, bromo, cyano, nitro, C 1 -C 4 alkylcarbonyl, and C 1 -C 4 alkoxycarbonyl;
R 5 for each occurrence, is independently selected from alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkyl, boronic acid ester, halogen, cycloalkyl, aryl, alkoxy, heterocycloalkyl, amino, and perhaloalkyl;
m and n are each independently an integer selected from 0 to 2;
R 6 and R 7 are each independently selected from hydrogen, hydroxy, and chiral groups selected from optionally substituted heteroalkyl, optionally substituted alkyl, optionally substituted aryl, optionally substituted cycloalkyl, halogen, carboxy, alkylcarbonyl, alkoxycarbonyl, optionally substituted alkoxy, and aminocarbonyl or may be taken together with any intervening atoms to form a group selected from oxo and optionally substituted cycloalkyl; and
B and B′ are each independently selected from hydrogen, chiral groups selected from optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, and optionally substituted cycloalkyl, or wherein B and B′ are taken together with any intervening atoms to form a group selected from optionally substituted cycloalkyl.

4. The compound of claim 3 , wherein:
R 1 is selected from —OCF 3 , —OCF 2 CF 3 , CF 3 , CF 2 CF 3 , bromo, cyano, nitro, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, and phenyl;
R 5 for each occurrence is independently selected from methyl, ethyl, bromo, chloro, fluoro, methoxy, ethoxy and CF 3;
R 6 and R 7 are each independently selected from methyl, ethyl, propyl and butyl; and
B and B′ are each independently selected from phenyl substituted with one or more groups independently selected from aryl, heteroaryl, heterocycloalkyl, alkyl, alkenyl, alkynyl, alkoxy, halogen, amino, alkylcarbonyl, carboxy, and alkoxycarbonyl.

5. The compound of claim 1 , selected from:
3,3-bis(4-methoxyphenyl)-12-bromo-6,13,13-trimethyl-3H,13H-indeno [2 ′,3′:3,4]naphtho[1,2-b]pyran;
3,3-bis(4-methoxyphenyl)-6,7-dimethoxy-10,12-bis(trifluoromethyl)-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;
3,3-bis(4-methoxyphenyl)-10,12-dibromo-6,7-dimethoxy-11,13,13-trimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;
3 -(4-butoxyphenyl)-3-(4-methoxyphenyl)-10,12-dibromo-6-trifluromethyl-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;
3,3-bis(4-fluorophenyl)-10,12-dibromo-6-trifluromethyl-13,13 -dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;
3,3 -bis(4-methoxyphenyl)-10,12-dibromo-13,13 -dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;
3-(4-fluorophenyl)-3-(4-(piperidin-1-yl)phenyl)-10,12-dibromo-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran; and/or
3-phenyl-3-(4-morpholinophenyl)-6,7-dimethoxy-12-trifluoromethyl-13,13-dimethyl-indeno[2′,3′:3,4]naphtho[1,2-b]pyran.

6. The compound of claim 1 , wherein said compound is a photochromic compound.

7. A photochromic composition comprising the photochromic compound of claim 6 and optionally at least one complementary photochromic compound.

8. A photochromic composition comprising at least one compound of claim 6 incorporated into at least a portion of an organic material, said organic material being a polymeric material, an oligomeric material, a monomeric material or a mixture or combination thereof.

9. The photochromic composition of claim 8 wherein said polymeric material comprises liquid crystal materials, self-assembling materials, polycarbonate, polyamide, polyimide, poly(meth)acrylate, polycyclic alkene, polyurethane, poly(urea)urethane, polythiourethane, polythio(urea)urethane, polyol(allyl carbonate), cellulose acetate, cellulose diacetate, cellulose triacetate, cellulose acetate propionate, c

Assignees

• He Meng
• Dabideen Darrin R
• Dai Xiao-Man
• Xiao Wenjing
• Xu Ruisong
• Mondal Sujit
• Kumar Anil
• Chopra Anu
• Transitions Optical Inc

Inventors

• He Meng
• Dabideen Darrin R
• Dai Xiao-Man
• Xiao Wenjing
• Xu Ruisong
• Mondal Sujit
• Kumar Anil
• Chopra Anu

Classifications

• G03F7/004

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• G03F7/0047

  characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing · CPC title

• G03F7/0387

  Polyamides or polyimides · CPC title

• G03F7/0041

  providing an etching agent upon exposure (G03F7/075 takes precedence; photolytic halogen compounds G03F7/0295) · CPC title

• G03F7/028

  with photosensitivity-increasing substances, e.g. photoinitiators · CPC title