Curcuminophore - Complexes with high fluorescence quantum yield for bioimaging

BACKGROUND

Finding new compounds having all the characteristics to become attractive candidates as fluorescent reporters is complex. Especially, dyes emitting in the Near Infrared (NIR) using two-photon excitation in the NIR region are of great interest for use in cell imaging because both excitation and detection operate in the biological transparency window.

Curcuminoid structures containing the borondifluoride unit have been shown as efficient emitters that fulfill many of the previous requirements. However, this work also led to the conclusion that solid-state fluorescence arose from highly stacked chromophores that limit the fluorescence quantum yield to ca. 5%. This invention is able to solve this problem.

HOW IT WORKS

The present invention relates to new borondifluoride complexes of curcuminoid compounds with an enhanced fluorescence quantum yield and emission.

Compounds of the invention, display a high fluorescence quantum yield (12.5% in water with maximum emission at 692 nm), and a good value of the two-photon absorption cross section (560 GM in water with excitation at 850 nm), therefore are very promissing fluorophores.

These fluorophores show improved NIR emitting properties particularly useful in the solid state for imaging applications, for example.

KEY BENEFITS vs. STATE OF THE ART

• High fluorescence quantum yield
• Enhanced optical properties in solution, such as high optical brightness at one and two photon excitation
• Photo luminescent behavior both in solid state and in solution
• Large two-photon absorption cross sections
• Simple, short (3 steps) and versatile synthesis
• Easy structural modification and tunable properties

DEVELOPMENT STATUS

Technical development to validate the most pertinent bioimaging application

APPLICATIONS

Bioimaging, organic laser, photodetector