IP Library Granted Patent US 11,982,676
Granted Patent B2
US 11,982,676 · App. 17/232,419 · Granted May 14, 2024

Near-infrared fluorescent nanoprobe

Inventors: Richard Martel (Montréal, CA); Étienne Gaufrès (Talence, FR); Charlotte Allard (Montréal, CA)
Assignees: VALORISATION-RECHERCHE, LIMITED PARTNERSHIP; POLYVALOR, LIMITED PARTNERSHIP; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
G01N33/587G01N21/6428G01N21/6456G01N33/582C09K11/06G01N2021/6439
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Quick Facts
Patent No.
US 11,982,676
App. No.
17/232,419
Granted
May 14, 2024
Kind
B2
Abstract

A fluorescent probe having a capsule of nanometric size and an aggregate of fluorogenic molecules coupled to the capsule is provided. The aggregate emits a fluorescent signal at one or more wavelengths within the fluorescence spectral range when the probe is illuminated by an excitation light beam at one or more wavelengths within the excitation spectral range. Preferably, the fluorescent spectral range is in the near-infrared region of the spectrum. In some embodiments, the capsule is a boron nitride (BN) nanotube and the aggregate comprise 3,6-Bis[2,2′]bithiophenyl-5-yl-2,5-di-n-octylpyrrolo[3,4-c]pyrrole-1,4-dione as fluorogenic molecules. In some embodiments, the 3,6-Bis[2,2′]bithiophenyl-5-yl-2,5-di-n-octylpyrrolo[3,4-c]pyrrole-1,4-dione fluorogenic molecules are in a J-aggregation state.

Claims (20)

1. A fluorescent probe comprising a capsule of nanometric size, the capsule being a boron nitride nanotube, the fluorescent probe further comprising an aggregate of fluorogenic molecules coupled to the capsule, the aggregate emitting a fluorescent signal at one or more wavelengths within a near-infrared fluorescence spectral range when the probe is illuminated by an excitation light beam at one or more wavelengths within a visible or NIR1 excitation spectral range.

2. The fluorescent probe according to claim 1 , wherein the aggregate comprise 3,6-Bis[2,2′]bithiophenyl-5-yl-2,5-di-n-octylpyrrolo[3,4-c]pyrrole-1,4-dione as fluorogenic molecules.

3. The fluorescent probe according to claim 1 , wherein the fluorogenic molecules are in a J-aggregation state.

4. The fluorescent probe according to claim 1 , wherein the fluorogenic molecules are in a combination of a J-aggregation state and a H-aggregation state.

5. The fluorescent probe according to claim 1 , wherein the fluorescent spectral range of the aggregate of fluorogenic molecules is shifted with respect to a fluorescent emission spectrum of said fluorogenic molecules in a free state by a spectral shift of the order of 600 nm.

6. The fluorescent probe according to claim 1 , wherein the fluorescent spectral range of the aggregate of fluorogenic molecules is broadened with respect to a fluorescent emission spectrum of said fluorogenic molecules in a free state.

7. The fluorescent probe according to claim 1 , wherein the fluorescent signal comprises multiple peaks in the NIR2 range upon excitation by the excitation light beam at a wavelength in the NIR1 range.

8. A fluorescent probe, comprising a capsule of nanometric size and an aggregate of fluorogenic molecules coupled to the capsule, the aggregate emitting a fluorescent signal at one or more wavelengths within a near-infrared fluorescence spectral range when the probe is illuminated by an excitation light beam at one or more wavelengths within a visible or NIR1 excitation spectral range, the aggregate comprising 3,6-Bis[2,2′]bithiophenyl-5-yl-2,5-di-n-octylpyrrolo[3,4-c]pyrrole-1,4-dione as fluorogenic molecules.

9. The fluorescent probe according to claim 8 , wherein the fluorogenic molecules are in a J-aggregation state.

10. The fluorescent probe according to claim 8 , wherein the fluorogenic molecules are in a combination of a J-aggregation state and a H-aggregation state.

11. The fluorescent probe according to claim 8 , wherein the fluorescent spectral range of the aggregate of fluorogenic molecules is shifted with respect to a fluorescent emission spectrum of said fluorogenic molecules in a free state by a spectral shift of the order of 600 nm.

12. The fluorescent probe according to claim 8 , wherein the fluorescent spectral range of the aggregate of fluorogenic molecules is broadened with respect to a fluorescent emission spectrum of said fluorogenic molecules in a free state.

13. The fluorescent probe according to claim 8 , wherein the fluorescent signal comprises multiple peaks in the NIR2 range upon excitation by the excitation light beam at a wavelength in the NIR1 range.

14. A fluorescent probe, comprising a capsule of nanometric size and an aggregate of fluorogenic molecules coupled to the capsule, the fluorogenic molecules being in a combination of a J-aggregation state and a H-aggregation state the aggregate emitting a fluorescent signal at one or more wavelengths within a near-infrared fluorescence spectral range when the probe is illuminated by an excitation light beam at one or more wavelengths within a visible or NIR 1 excitation spectral range.

15. The fluorescent probe according to claim 14 , wherein:

the capsule is a boron nitride nanotube; and

the aggregate comprise 3,6-Bis[2,2′]bithiophenyl-5-yl-2,5-di-n-octylpyrrolo[3,4-c]pyrrole-1,4-dione as fluorogenic molecules.

16. The fluorescent probe according to claim 14 , wherein the fluorescent spectral range of the aggregate of fluorogenic molecules is shifted with respect to a fluorescent emission spectrum of said fluorogenic molecules in a free state by a spectral shift of the order of 600 nm.

17. The fluorescent probe according to claim 14 , wherein the fluorescent spectral range of the aggregate of fluorogenic molecules is broadened with respect to a fluorescent emission spectrum of said fluorogenic molecules in a free state.

18. The fluorescent probe according to claim 14 , wherein the fluorescent signal comprises multiple peaks in the NIR2 range upon excitation by the excitation light beam at a wavelength in the NIR1 range.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2024
From: MARTEL, RICHARD
To: UNIVERSITÉ DE MONTRÉAL
Reel/Frame 066913/0851 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2024
From: UNIVERSITÉ DE MONTRÉAL
To: VALORISATION-RECHERCHE, LIMITED PARTNERSHIP
Reel/Frame 066913/0969 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2024
From: ALLARD, CHARLOTTE
To: CORPORATION DE L'ECOLE POLYTECHNIQUE DE MONTREAL
Reel/Frame 066914/0193 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2024
From: CORPORATION DE L’ECOLE POLYTECHNIQUE DE MONTREAL
To: POLYVALOR, LIMITED PARTNERSHIP
Reel/Frame 066914/0314 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2024
From: GAUFRES, ETIENNE
To: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
Reel/Frame 066914/0425 →
Continuity (1)
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