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US 11,279,677 B2Granted
Photochromic hydrazone switches
AssigneeTrustees of Dartmouth College
InventorsIvan Abrahamian, Hai Qian, Susnata Pramanik, Baihao Shao, Quan Li
Life of this patent
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Abstract
Provided herein are compounds for use as photochromic molecular switches having very long thermal isomerization half-lives and switchable fluorescence properties both in solution and the solid state.
Claims13
A compound of Formula I or a salt thereof:
- wherein
- represents a double bond having either E or Z stereochemistry;
- A is phenyl or naphthyl;
- B is phenyl or pyridine-2-yl;
- R is O—R′,
- where:
- R′ is azide, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, alkoxyalkyl, heteroalkyl, alkoxy, aryl, or heteroaryl,
- where in the alkenyl and alkynyl groups for R′, the double or triple bond is not at the alpha-beta position in the alkenyl or alkynyl group;
- R1 and R2 are independently, for each occurrence, selected from the group consisting of heterocyclyl, halo, alkylamino, dialkylamino, diphenyl amino, hydroxyl, nitro, cyano, carboxyl, carboxylalkyl and carboxamido;
- or
- R and one of R2 are optionally linked by a 3-8 carbon linker, which is optionally substituted;
- n is 0, 1, 2, 3, 4 or 5;
- and
- m is 0, 1, 2, 3, 4, 5, 6 or 7;
- provided that when n and m are both 0, at least one of A and B is not phenyl.
12 more elements
A method of optically switching a compound of Formula I, or a salt thereof, or a material comprising the compound of Formula I or a salt thereof:
- wherein
- represents a double bond having either E or Z stereochemistry;
- A is phenyl or naphthyl;
- B is phenyl or pyridine-2-yl;
- R is O—R′,
- where:
- each R′ is independently azide, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, alkoxyalkyl, heteroalkyl, alkoxy, aryl, or heteroaryl,
- where in the alkenyl and alkynyl groups for R′, the double or triple bond is not at the alpha-beta position in the alkenyl or alkynyl group;
- R1 and R2 are independently, for each occurrence, selected from the group consisting of heterocyclyl, halo, alkylamino, dialkylamino, diphenyl amino, hydroxyl, nitro, cyano, carboxyl, carboxylalkyl and carboxamido;
- or
- R and one of R2 are optionally linked by a 3-8 carbon linker, which is optionally substituted;
- n is 0, 1, 2, 3, 4 or 5;
- and
- m is 0, 1, 2, 3, 4, 5, 6 or 7;
- provided that when n and m are both 0, at least one of A and B is not phenyl;
- the method comprising irradiating said compound or material, thereby isomerizing the compound from the E stereoisomer to the Z stereoisomer, isomerizing the compound from the Z stereoisomer to the E stereoisomer.
13 more elements
Dependencies are inferred from the claim text.