IP Library › Granted Patent US 12,466,836
Granted Patent B2
US 12,466,836 · App. 17/697,286 · Granted Nov 11, 2025

Spiropyran hydrogels and light-driven expansion thereof

Inventors: Chuang Li (Evanston, IL); Samuel I. Stupp (Evanston, IL)
Assignee: Northwestern University
C07D491/107C08F222/1063C08F2800/10C08F2810/20C08F2810/50
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Quick Facts
Patent No.
US 12,466,836
App. No.
17/697,286
Filed
Mar 17, 2022
Granted
Nov 11, 2025
Kind
B2
Art Unit
1767
USPC
524/808
Abstract

Provided herein are sulfonate-based water-soluble photoswitches that, in contrast to existing systems, trigger a volumetric expansion in hydrogels upon exposure to photons; contraction is in turn observed under dark conditions in a highly reversible manner.

Claims (41)

1 . A compound of formula (I):

or a salt thereof, wherein:

R 1 is —SO 3 H;

R 2 is selected from hydrogen and —SO 3 H;

R 3 is selected from hydrogen and methyl;

m and n are each independently 0, 1, or 2; and

R 4 and R 5 are each independently selected from C 1 -C 3 alkyl, C 1 -C 3 alkoxy, halo, and nitro.

2 . The compound of claim 1 , or a salt thereof, wherein R 1 and R 2 are both —SO 3 H.

3 . The compound of claim 1 , or a salt thereof, wherein R 3 is methyl.

4 . The compound of claim 1 , or a salt thereof, wherein m and n are 0.

5 . The compound of claim 1 , wherein the compound is selected from:

or a salt thereof.

6 . The compound of claim 1 , wherein the compound is a sodium salt or a potassium salt.

7 . The compound of claim 6 , wherein the compound is selected from:

8 . A compound of formula (Ia):

or a salt thereof, wherein:

R 1 is —SO 3 H;

R 2 is selected from hydrogen and —SO 3 H;

m and n are each independently 0, 1, or 2; and

R 4 and R 5 are each independently selected from C 1 -C 3 alkyl, C 1 -C 3 alkoxy, halo, and nitro.

9 . A polymer comprising a monomer unit of formula (II):

or a salt thereof, wherein:

R 1 is —SO 3 H;

R 2 is selected from hydrogen and —SO 3 H;

R 3 is selected from hydrogen and methyl;

m and n are each independently 0, 1, or 2; and

R 4 and R 5 are each independently selected from C 1 -C 3 alkyl, C 1 -C 3 alkoxy, halo, and nitro,

wherein each

represents a point of attachment to the polymer chain.

10 . The polymer of claim 9 , or a salt thereof, wherein R 1 and R 2 are both —SO 3 H.

11 . The polymer of claim 9 , or a salt thereof, wherein R 3 is methyl.

12 . The polymer of claim 9 , or a salt thereof, wherein m and n are 0.

13 . The polymer of claim 9 , wherein the monomer unit has a formula selected from:

or a salt thereof.

14 . The polymer of claim 13 , wherein the monomer unit is in sodium or potassium salt form.

15 . The polymer of claim 14 , wherein the monomer unit has a formula selected from:

16 . The polymer of claim 9 , further comprising one or more additional monomers selected from N-isopropylacrylamide, di(ethylene glycol) methyl ether methacrylate, oligo(ethylene glycol) methyl ether methacrylate, and any combination thereof.

17 . The polymer of claim 9 , further comprising one or more crosslinking monomers.

18 . The polymer of claim 17 , wherein the crosslinking monomer is N,N′-methylenebis(acrylamide).

19 . A method of triggering volumetric expansion of a hydrogel comprising a compound of claim 1 , the method comprising exposing the hydrogel to light.

20 . A method of triggering volumetric contraction of a hydrogel comprising a compound of claim 1 , the method comprising exposing the hydrogel to darkness.

Assignments (2)
CONFIRMATORY LICENSE Recorded May 9, 2023
From: NORTHWESTERN UNIVERSITY
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 063578/0551 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2022
From: LI, CHUANG; STUPP, SAMUEL I
To: NORTHWESTERN UNIVERSITY
Reel/Frame 061058/0823 →
Continuity (2)
Provisional Application 63162268 · Mar 17, 2021
Related Publication 20220298169A1 · Sep 22, 2022
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