Visible light‐induced photodeoxygenation of polycyclic selenophene Se‐oxides

Abstract

AbstractPhotodeoxygenation of dibenzothiophene S‐oxide (DBTO) is believed to produce ground‐state atomic oxygen [O(3P)] in solution. Compared with other reactive oxygen species (ROS), O(3P) is a unique oxidant as it is potent and selective. Derivatives of DBTO have been used as O(3P)‐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]selenophene Se‐oxide, benzo[b]naphtho[2,1‐d]selenophene Se‐oxide, dinaphtho[2,3‐b:2’,3’‐d]selenophene Se‐oxide, and perylo[1,12‐b,c,d]selenophene Se‐oxide were synthesized, and their ability to utilize visible light for generating O(3P) was interrogated. Benzo[b]naphtho[1,2‐d]selenophene Se‐oxide produces O(3P) upon irradiation centered at 420 nm. Additionally, benzo[b]naphtho[1,2‐d]selenophene Se‐oxide, benzo[b]naphtho[2,1‐d]selenophene Se‐oxide, and dinaphtho[2,3‐b:2’,3’‐d]selenophene Se‐oxide produce O(3P) 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(3P) in solution.