Visible light‐induced photodeoxygenation of polycyclic selenophene Se ‐oxides
Visible light‐induced photodeoxygenation of polycyclic selenophene Se ‐oxides
复制标题
可见光诱导多环硒酚硒氧化物的光脱氧
DOI：
10.1002/poc.4144
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发表时间：
2020
影响因子：
1.8
通讯作者：
McCulla, Ryan D.
中科院分区：
文献类型：
--
作者：
Chintala, Satyanarayana M.;Throgmorton, John C.;Maness, Peter F.;McCulla, Ryan D.
二苯并硫代硫氧化物(DBTO)的光脱氧反应被认为是在溶液中产生基态原子氧[O(3P)]。与其他活性氧物种(ROS)相比，O(3P)是一种独特的氧化剂，具有较强的活性和选择性。DBTO的衍生物已被用作O(3P)的前体，用于氧化各种分子，包括质粒DNA、蛋白质、脂类、硫醇和其他有机小分子。不幸的是，DBTO的光脱氧需要紫外光照射，这不是生物系统的理想波长范围，并且量子产率低，约为0.003。本工作合成了苯并[b]萘并[1，2-d]硒氧化物、苯并[b]萘并[2，1-d]硒氧化物、二氮杂并[2，3-b：2‘，3’-d]硒氧化物和并[1，12-b，c，d]硒氧化物，考察了它们利用可见光产生O(3P)的能力。苯并[b]萘并[1，2-d]硒-氧化物在420 nm处照射产生O(3P)。另外，苯并[b]萘并[1，2-d]硒氧化物、苯并[b]萘并[2，1-d]硒氧化物和二氮杂并[2，3-b：2‘，3’-d]硒氧化物在紫外光照射下产生O(3P)，光脱氧量子产率在0.009~0.33%之间。这项工作通过扩大可用于在溶液中产生O(3P)的波长范围来增加光脱氧的效用。
Photodeoxygenation of dibenzothiopheneS‐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]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(3P) was interrogated. Benzo[b]naphtho[1,2‐d]selenopheneSe‐oxide produces O(3P) 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(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.