Electron-Rich Polyclinic aromatic compounds containing a Boron-Nitrogen bond: Synthesis and Optical Properties
Disciplines
Chemistry | Materials Chemistry | Organic Chemistry
Abstract (300 words maximum)
Dyes that absorb in the visible and fluoresce in the red- and near-infrared (NIR) regions of the electromagnetic spectrum are gaining popularity in materials science. These dyes have been proven to be effective in photodynamic and photothermal therapy. Because of the undeniable biological benefits of red and NIR light, such as deep tissue penetration and little interference from background autofluorescence, these dyes are commonly utilized for high contrast bioimaging and detection in biological systems. However, majority of these dyes have limited solubility and/or fluorescence, making them unsuitable for use in a variety of biological applications. To address low fluorescence, we synthesized, characterized, and investigated new fluorescent dyes with a boron-nitrogen bond, known as polycyclic 1,2-BN-heteroarene. These dyes have a flat and rigid scaffold with a highly conjugated π-system to optimize optical properties and allow for absorption and emission at long wavelengths and high fluorescence. To increase solubility, we added a diphenyl propeller-shaped moiety to the scaffold's left hemisphere. This decreases π-π stacking interactions, improves solubility, and enables multifunctional fluorescent materials. The diphenyl propeller shape is also an efficient electron donor, generating intramolecular charge transfer (ICT) and red/NIR emission. These discoveries will help to design future electron-rich polycyclic heteroarene dyes containing a Boron-Nitrogen bond for bioimaging and detection in living organisms with low interference from background autofluorescence.
Academic department under which the project should be listed
CSM - Chemistry and Biochemistry
Primary Investigator (PI) Name
Carl J Saint-Louis
Electron-Rich Polyclinic aromatic compounds containing a Boron-Nitrogen bond: Synthesis and Optical Properties
Dyes that absorb in the visible and fluoresce in the red- and near-infrared (NIR) regions of the electromagnetic spectrum are gaining popularity in materials science. These dyes have been proven to be effective in photodynamic and photothermal therapy. Because of the undeniable biological benefits of red and NIR light, such as deep tissue penetration and little interference from background autofluorescence, these dyes are commonly utilized for high contrast bioimaging and detection in biological systems. However, majority of these dyes have limited solubility and/or fluorescence, making them unsuitable for use in a variety of biological applications. To address low fluorescence, we synthesized, characterized, and investigated new fluorescent dyes with a boron-nitrogen bond, known as polycyclic 1,2-BN-heteroarene. These dyes have a flat and rigid scaffold with a highly conjugated π-system to optimize optical properties and allow for absorption and emission at long wavelengths and high fluorescence. To increase solubility, we added a diphenyl propeller-shaped moiety to the scaffold's left hemisphere. This decreases π-π stacking interactions, improves solubility, and enables multifunctional fluorescent materials. The diphenyl propeller shape is also an efficient electron donor, generating intramolecular charge transfer (ICT) and red/NIR emission. These discoveries will help to design future electron-rich polycyclic heteroarene dyes containing a Boron-Nitrogen bond for bioimaging and detection in living organisms with low interference from background autofluorescence.