Discriminating molecule family for neutron and gamma radiation

• US 8,389,940 B2
• Filed: 07/10/2009
• Issued: 03/05/2013
• Est. Priority Date: 07/11/2008
• Status: Expired due to Fees

• Current Assignee: Centre National De La Recherche Scientifique
• Original Assignee: Universite Louis Pasteur De Strasbourg
• Inventors: Barillon, Remi, Bouajila, Ezeddine, Douce, Laurent, Jung, Jean-Marc, Stuttge, Louise
• Primary Examiner(s): Kim, Kiho
• Application Number:
  US13/003,646
• Publication Number:
  US 20110303850A1
• Time in Patent Office: 1,334 Days
• Field of Search: 250/362
• US Class Current: 250/362
• CPC Class Codes: C07D 413/10 linked by a carbon chain containing aromatic rings

Abstract

The invention relates to a novel discriminating molecule family for neutron and gamma radiation, and to the preparation method thereof. Said molecules are also useful for detecting radiation (X, gamma, electrons, protons, ions), and thus for manufacturing radar, and industrial or medical dosimetry instruments.

Claims

1. Method for detecting gamma, X, neutron, proton radiation, comprising the step of detecting the fluorescence of a fluorophore compound F₁ carrying an organic cationic group combined with a counter-anion, or else carrying an anionic group combined with an organic counter-cation, said cationic group or organic counter-cation comprising at least one heteroatom chosen from among N, S or P carrying a positive charge.

2. The method according to claim 1, wherein the fluorophore compound F₁ carries an organic cationic group combined with a counter-anion.

3. The method according to claim 2, wherein the organic cationic group is a heterocyclic group optionally substituted by one to three groups chosen from among R^1a, R^1b, R^1c or R²⁵,

or else the organic cationic group is a group (a), (b), (c) or (d):

4. The method according to claim 3 of a compound of formula (A):

L*-Y—

Z⁺⁻

X

wherein;

Z⁺ is an organic caitonic group such as defined in claim 3,

X⁻

is an organic or inorganic anion,

Y is a C₁-C₆ alkylene group or;

(C₁-C₄ alkylene)_m-Q-(C₁-C₄ alkylene)_n group;

C₆-C₁₀ arylene group;

wherein the alkylene, arylene groups are optionally substituted by 1 to 3 R²⁰ groups;

Q is a group from among —

C(═

O)—

, —

NR²¹C(═

O)—

, —

C(═

O)NR²¹—

, —

C(═

O)O—

, —

OC(═

O)—

, —

O—

, —

NR²¹—

, —

S(O)_y—

, —

CR²¹═

CR²¹—

, —

C≡

C—

, C₆-C₁₀ arylene, 5-10-membered heteroarylene, C₃-C₆ cycloalkylene or 3- to 6-membered heterocycloalkylene,

wherein said arylene, heteroarylene, cycloalkylene groups are optionally substituted by 1 to 3 R²⁰ groups;

L* is a fluorophore group,

m is 0 or 1;

n is 0 or 1;

y is 0, 1 or 2,

The R²⁰and R²¹ groups being such as defined in claim 3.

5. The method according to claim 1, to discriminate between proton/gamma, proton/X, neutron/gamma, neutron/X, alpha/gamma, alpha/X, gamma ion/X ion radiation.

6. The method according to claim 1, wherein the organic cationic group is a heterocyclic group comprising at least one nitrogen atom.

7. The method according to claim 1, wherein the organic cationic group is a group chosen from among pyridil, imidazolyl, imidazolidinyl, oxazolyl, oxazolidinyl, thiazolyl, thiazolidinyl, pyrazolyl, triazolyl, tetrazolyl, benzotriazolyl, benzotriazolyle a guanine group, a caprolactam group.

8. The method according to claim 1, wherein the fluorophore compound F₁ carrying a cationic or anionic group is an oxazolyl, oxadiazolyl anthracenyl, phenanthrenyl radical.

9. The method according to claim 1, wherein the fluorophore compound F1 of formula (I):

10. The method according to claim 9, wherein the compound of formula (A) is of formula (Ia):

11. The method according to claim 1, comprising a step of manufacture of radar and industrial or medical dosimetry instruments, with a fluorophore compound according to claim 1.

16. The compound of formula (I) according to claim 15, characterized in that it meets formula (Ia):

17. The compound of formula (I) according to claim 16, wherein R^1a is a C₁-C₁₆ alkyl group.

18. The compound of formula (I) according to claim 17, wherein R^1b and R^1c are both H.

19. Method for preparing a compound of formula (Ia) comprising the reaction of a compound of formula (II) with a compound of formula (III):

12. Fluorophore compound F₁ carrying an organic cation group combined with a counter-anion, or else carrying an anionic group combined with an organic counter-cation, said cationic group or counter-cation comprising at least one heteroatom chosen from among N, S or P carrying a positive charge, wherein the fluorophore group F₁ is not an anthracenyl group.

13. The compound according to claim 12, wherein the fluorophore group is chosen from among an oxazolyl, oxadiazolyl or phenanthrenyl radical.

14. The compound according to claim 13, wherein the fluorophore group F₁ is an oxazolyl radical.

15. The compound of formula (I) according to claim 14:

20. The compound according to claim 12, wherein U is CR²⁶.

21. The compound according to claim 20, wherein U is CH.

22. The compound according to claim 12, wherein Y is a C₁-C₆ alkylene group.

23. The compound according to claim 22, wherein Y is CH₂.

24. The compound of formula (I) according to claim 12, wherein X⁻

is an anion chosen from among a halide, P(R⁴)₆⁻

, B(R⁴)₄⁻

, SCN<sup>−

, (R5</sup>SO₂)₂N⁻

, R⁵OSO₃, R⁵SO₃⁻

, carborane, carbonate, hydrogenocarbonate, alcoholate, carboxylate, amide, phosphate, SiF₆⁻

, SbF₆⁻

, I₃⁻

, nitrate, halide oxide, silicate, sulphate, sulphonate, cyanide, carbanion or metallate, wherein;

R⁴, on each occurrence, is a group independently chosen from among a halogen atom, C₁-C₆ alkyl group, C6-C₁₀ aryl group, arylalkyl group;

R⁵, on each occurrence, is a group independently chosen from among C₁-C₂₀ alkyl, C₁-C₂₀ halogenoalkyl, C₆-C₁₀ aryl, arylalkyl.

25. The compound according to claim 12, wherein X⁻

is chosen from among Br, PF₆⁻

, BF₄⁻

, (CF₃SO₂)₂N⁻

, C₁₂H₂₅OSO₃⁻

, C₁₆H₃₃OSO₃⁻

, CF₃SO₃⁻

.

26. The compound according to claim 12, chosen from among:

1-methyl-3-[4-(5-phenyl-oxazol-2-yl)-benzyl]-3H-imidazol-1-ium bromide,

1-hexyl-3-[4-(5-phenyl-oxazol-2-yl)-benzyl]-3H-imidazol-1-ium bromide,

1-octyl-3-[4-(5-phenyl-oxazol-2-yl)-benzyl]-3H-imidazol-1-ium bromide,

1-decyl-3-[4-(5-phenyl-oxazol-2-yl)-benzyl]-3H-imidazol-1-ium bromide,

1-dodecyl-3-[4-(5-phenyl-oxazol-2-yl)-benzyl]-3H-imidazol-1-ium bromide,

3-[4-(5-phenyl-oxazol-2-yl)-benzyl]-1-tetradecyl-3H-imidazol-1-ium bromide,

1-hexadecyl-3-[4-(5-phenyl-oxazol-2-yl)-benzyl]-3H-imidazol-1-ium bromide,

1-hexadecyl-3-[4-(5-phenyl-oxazol-2-yl)-benzyl]-3H-imidazol-1-ium hexafluorophosphate,

1-hexadecyl-3-[4-(5-phenyl-oxazol-2-yl)-benzyl]-3H-imidazol-1-ium bis(trifluoromethylsulphonyl)imide,

1-hexadecyl-3-[4-(5-phenyl-oxazol-2-yl)-benzyl]-3H-imidazol-1-ium dodecyl sulphate,

1-hexadecyl-3-[4-(5-phenyl-oxazol-2-yl)-benzyl]-3H-imidazol-1-ium hexadecyl sulphate.

27. Material comprising a fluorophore compound according to claim 12.

28. The material according to claim 27, characterized in that it is a transparent plastic material.