AB - A set polyethylene glycol (PEG)-appended BODIPY architectures (BOPEG1-BOPEG3) have been prepared and studied in CH2Cl2, H2O:CH3CN (1:1) and aqueous solutions. BOPEG1 and BOPEG2 both contain a short PEG chain and differ in substitution about the BODIPY framework. BOPEG3 is comprised of a fully substituted BODIPY moiety linked to a PEG polymer that is roughly 13 units in length. The photophysics and electrochemical properties of these compounds have been thoroughly characterized in CH2Cl2 and aqueous CH3CN solutions. The behavior of BOPEG1-BOPEG3 correlates with established rules of BODIPY stability based on substitution about the BODIPY moiety. Electrogenerated chemiluminescence (ECL) for each of these compounds was also monitored. BOPEG1, which is unsubstituted at the 2- and 6-positions dimerized upon electrochemical oxidation while BOPEG2, which contains ethyl groups at the 2- and 6-positions, was much more robust and served as an excellent ECL luminophore. BOPEG3 is highly soluble in water due to the long PEG tether and demonstrated modest ECL activity in aqueous solutions using tri-n-propylamine (TPrA) as a coreactant. As such, BOPEG3 represents the first BODIPY derivative that has been shown to display ECL in water without the need for an organic cosolvent, and marks an important step in the development of BODIPY based ECL probes for various biosensing applications.
Solar Energy Conversion, Organic Photovoltaics, Artificial Photosynthesis, Porphyrin Synthesis and Spectroscopy, Self-Assembly, Photodynamic Therapy, Dendrimer synthesis, Electron-Transfer Reactions, Time-Resolved Laser Spectroscopy, Photophysics and Photochemistry.
Synthesis and photophysics of 6-dimethylaminopurine …
Photophysical Properties of Unusual Porphyrins and Porphyrinoids
My group also synthesizes and studies the optical properties (steady state and ultrafast time-resolved) of unusual porphyrins and porphyrinoids. In particular, we are interested in using the tautomerism inherent to certain classes of porphyrins to influence excited state chemistry.