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Visible light‐induced photodeoxygenation of polycyclic selenophene Se‐oxides
Journal of Physical Organic Chemistry ( IF 1.8 ) Pub Date : 2020-09-22 , DOI: 10.1002/poc.4144
Satyanarayana M. Chintala 1 , John C. Throgmorton 1 , Peter F. Maness 1 , Ryan D. McCulla 1
Affiliation  

Photodeoxygenation 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.

中文翻译:

可见光诱导的多环硒氧化物的光脱氧

据信二苯并噻吩S-氧化物(DBTO)的光脱氧在溶液中产生基态原子氧[O(3 P)]。与其他活性氧(ROS)相比,O(3 P)具有强效和选择性,是一种独特的氧化剂。DBTO的衍生物已被用作O(3 P)的前体,以氧化多种分子,包括质粒DNA,蛋白质,脂质,硫醇和其他小有机分子。不幸的是,DBTO的光脱氧需要紫外线照射,这对于生物系统而言不是理想的波长范围,并且具有约0.003的低量子产率。在这项工作中,苯并[ b ]萘[1,2- d ]硒烯Se-氧化物,苯并[b ]萘并[2,1- d ]硒吩氧化物,二萘并[2,3- b:2' ,3'- d ]硒吩氧化物,和perylo [1,12- B,C,d ]硒吩合成了Se-氧化物,并研究了它们利用可见光生成O(3 P)的能力。苯并[ b ]萘[1,2- d ]硒烯Se-氧化物在420 nm处辐照会产生O(3 P)。此外,苯并[ b ]萘并[1,2- d ]硒吩氧化物,苯并[ b ]萘并[2,1- d]硒烯Se-氧化物和二萘并[2,3- b:2',3'- d ]硒烯Se-氧化物在用UVA光照射时会产生O(3 P),并且光脱氧的量子产率在0.009至0.33之间。这项工作通过扩展可用于在溶液中生成O(3 P)的波长范围,增加了光脱氧的实用性。
更新日期:2020-09-22
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