Department of Chemistry and Biochemistry, University of Arizona, 1306 East University Boulevard, Tucson, Arizona 85721, United States.
J Am Chem Soc. 2015 Aug 12;137(31):9764-7. doi: 10.1021/jacs.5b04367. Epub 2015 Jul 31.
Controlling chemical reactivity using light is a longstanding practice within organic chemistry, yet little has been done to modulate the basicity of compounds. Reported herein is a triazabutadiene that is rendered basic upon photoisomerization. The pH of an aqueous solution containing the water-soluble triazabutadiene can be adjusted with 350 nm light. Upon synthesizing a triazabutadiene that is soluble in aprotic organic solvents, we noted a similar light-induced change in basicity. As a proof of concept we took this photobase and used it to catalyze a condensation reaction.
利用光控制化学反应活性是有机化学中的一项长期实践，但在调节化合物的碱性方面却鲜有尝试。本文报道了一种三氮杂丁二烯，其在光异构化后呈现碱性。含有水溶性三氮杂丁二烯的水溶液的 pH 值可以用 350nm 的光进行调节。在合成一种可溶于非质子有机溶剂的三氮杂丁二烯时，我们注意到碱性也会发生类似的光诱导变化。作为概念验证，我们使用这种光碱来催化缩合反应。
