Visible light-induced photodeoxygenation of polycyclic selenopheneSe-oxides

Photodeoxygenation of dibenzothiopheneS-oxide (DBTO) is believed to produce ground-state atomic oxygen [O(P-3)] in solution. Compared with other reactive oxygen species (ROS), O(P-3) is a unique oxidant as it is potent and selective. Derivatives of DBTO have been used as O(P-3)-precursors to oxidize variety of molecules, including plasmid DNA, proteins, lipids, thiols, and other small organic molecules. Unfortunately, the photodeoxygenation of DBTO requires ultraviolet irradiation, which is not an ideal wavelength range for biological systems, and has a low quantum yield of approximately 0.003. In this work, benzo[b]naphtho[1,2-d]selenopheneSe-oxide, benzo[b]naphtho[2,1-d]selenopheneSe-oxide, dinaphtho[2,3-b:2',3'-d]selenopheneSe-oxide, and perylo[1,12-b,c,d]selenopheneSe-oxide were synthesized, and their ability to utilize visible light for generating O(P-3) was interrogated. Benzo[b]naphtho[1,2-d]selenopheneSe-oxide produces O(P-3) upon irradiation centered at 420 nm. Additionally, benzo[b]naphtho[1,2-d]selenopheneSe-oxide, benzo[b]naphtho[2,1-d]selenopheneSe-oxide, and dinaphtho[2,3-b:2',3'-d]selenopheneSe-oxide produce O(P-3) when irradiated with UVA light and have quantum yields of photodeoxygenation ranging from 0.009 to 0.33. This work increases the utility of photodeoxygenation by extending the range of wavelengths that can be used to generate O(P-3) in solution.

Automated summary

This study expands the utility of photodeoxygenation by synthesizing and investigating the ability of benzoselenophene oxides to generate O(P-3) using visible light, thereby increasing the practicality of the photodeoxygenation process.