Fluorescent dibenzazole derivatives and methods related thereto

C - Chemistry – Metallurgy – 07 – D

Patent

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Details

C07D 277/64 (2006.01) C07D 263/62 (2006.01) C07D 277/66 (2006.01) C07D 417/06 (2006.01) C07F 9/653 (2006.01) C07F 9/6541 (2006.01) C07H 11/04 (2006.01) C07H 15/26 (2006.01) C07H 17/00 (2006.01) C07H 19/04 (2006.01) C07H 21/00 (2006.01) G01N 33/58 (2006.01) H04N 5/00 (2006.01)

Patent

CA 2295304

Dibenzazole compounds having general structure (I) and (II), wherein R1, R2, R3, R4, R5, R6 are independently H or a substituent which aids in solubility of the compound or which provides a linker arm for linking the compound to another moiety; Y is H or a cleavalable moiety; X is a hydrogen, halogen, CF3, or SO3H; V and W are oxygen or sulfur; Z is -C=C-, -CC- or an aromatic ring moiety; and n is 0, 1, or 2. When n=0 at least one of R1, R2, R3, R4, and R5 is a substituent which aids in solubility of the compound or which provides a linker arm for linking the compound to another moiety or X is a halogen, CF3 or SO3H. These compounds are highly fluorescent and can be easily detected using a fluorometer. Derivatives in which the Y group is a substituent other than H contain a fluorescence inhibiting chemical moiety that upon removal restores the fluorescence of the compound. Methods for their synthesis and application are provided.

L'invention concerne des composés de dibenzazole de structure générale (I) et (II), dans lesquelles; R¿1?; R¿2?, R¿3?, R¿4?, R¿5?, R¿6? sont indépendamment H ou un substituant qui contribue à la solubilité du composé ou qui constitue un bras de liaison permettant de lier le composé à une autre fraction; Y est H ou une fraction clivable; X est hydrogène, halogène, CF¿3?, ou SO¿3?H; V et W sont oxygène ou soufre; Z est -C=C-, -C?C- ou une fraction à noyau aromatique; et n est égal à 0, 1 ou 2. Lorsque n=0, l'un au moins de R¿1?; R¿2?, R¿3?, R¿4?, et R¿5? est un substituant qui contribue à la solubilité du composé ou qui constitue un bras de liaison permettant de lier le composé à une autre fraction ou Y est halogène, CF¿3?, ou SO¿3?H. Ces composés sont très fluorescents et peuvent être facilement détectés à l'aide d'un fluoromètre. L'invention concerne également des dérivés, dans lesquels le groupe Y est un substituant autre que H, renfermant une fraction chimique inhibant la fluorescence, qui une fois éliminée, redonne au composé sa fluorescence. L'invention concerne enfin des méthodes de synthèse et d'application de ces composés.

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