Multifunctional Electron-Rich Polycyclic 1,2-BN-Heteroarenes: Synthesis, Optical Properties, and Applications
Disciplines
Chemistry | Materials Chemistry | Organic Chemistry
Abstract (300 words maximum)
Dyes that absorb long wavelength light and emit in the red and near-infrared (NIR) region of the electromagnetic spectrum are gaining popularity in materials technology for use in optical recording and laser filters, as well as cell imaging markets such as photodynamic and photothermal therapy, all of which use reactive oxygen species or heat to kill tumor cells. The dye's molecular structure is critical for long-wavelength absorption and NIR emission. The scaffold should be planar and rigid, with a highly conjugated π-surface, to allow dyes to absorb and emit at longer wavelengths and improving optical properties. In this study, we introduce strong electron-donating groups (EDGs) into the left hemisphere of a planar boron-nitrogen (BN) doped polycyclic aromatic compound, polycyclic 1,2-BN-heteroarene scaffold, to create an intramolecular charge transfer process and investigate the effect of strong EDGs on the photophysical properties. We hypothesize that adding strong EDGs, such as aryl amino derivatives, to the left hemisphere of the scaffold of polycyclic 1,2-BN-heteroarene will increase the energy of the highest occupied molecular orbital (HOMO), reducing the HOMO-LUMO gap and resulting in absorption in the visible region of the electromagnetic spectrum and emission in the red and NIR regions. This investigation will advance meritorious research in the field of polycyclic BN-heteroarenes, as well as our understanding of the photophysical properties of electron-rich substituted polycyclic aromatic compounds containing a B-N bond and the impact of EDGs on multifunctional materials. These findings will help to develop future electron-rich polycyclic BN-heteroarene dyes for bioimaging, in which red and NIR light can safely penetrate human tissue without causing apoptosis or cell damage, as well as detection in living organisms with minimal 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
Multifunctional Electron-Rich Polycyclic 1,2-BN-Heteroarenes: Synthesis, Optical Properties, and Applications
Dyes that absorb long wavelength light and emit in the red and near-infrared (NIR) region of the electromagnetic spectrum are gaining popularity in materials technology for use in optical recording and laser filters, as well as cell imaging markets such as photodynamic and photothermal therapy, all of which use reactive oxygen species or heat to kill tumor cells. The dye's molecular structure is critical for long-wavelength absorption and NIR emission. The scaffold should be planar and rigid, with a highly conjugated π-surface, to allow dyes to absorb and emit at longer wavelengths and improving optical properties. In this study, we introduce strong electron-donating groups (EDGs) into the left hemisphere of a planar boron-nitrogen (BN) doped polycyclic aromatic compound, polycyclic 1,2-BN-heteroarene scaffold, to create an intramolecular charge transfer process and investigate the effect of strong EDGs on the photophysical properties. We hypothesize that adding strong EDGs, such as aryl amino derivatives, to the left hemisphere of the scaffold of polycyclic 1,2-BN-heteroarene will increase the energy of the highest occupied molecular orbital (HOMO), reducing the HOMO-LUMO gap and resulting in absorption in the visible region of the electromagnetic spectrum and emission in the red and NIR regions. This investigation will advance meritorious research in the field of polycyclic BN-heteroarenes, as well as our understanding of the photophysical properties of electron-rich substituted polycyclic aromatic compounds containing a B-N bond and the impact of EDGs on multifunctional materials. These findings will help to develop future electron-rich polycyclic BN-heteroarene dyes for bioimaging, in which red and NIR light can safely penetrate human tissue without causing apoptosis or cell damage, as well as detection in living organisms with minimal interference from background autofluorescence.