Using the 3-Diethylaminobenzyl Group as a Photocage in Aqueous Solution

The Journal of Organic Chemistry
Xiong Ding, Pengfei Wang

Abstract

We have demonstrated that the 3-diethylaminobenzyl (DEABn) photolabile protecting group (PPG) is an effective and structurally simple PPG for releasing molecules in aqueous environment. In general, the photoreaction is clean, and the released substrate and the PPG product, i.e., 3-diethylaminobenzyl alcohol, are obtained in high yield. The clean photoreaction can also be achieved under mild ambient conditions with sunlight, while the reactant is stable under indoor lighting. Release of two substrates from one PPG chromophore in aqueous solution has been demonstrated to be feasible. We have also compared the uncaging properties of the DEABn and the widely used o-nitrobenzyl ( o-NB) group, given their comparable structural simplicity. With its clean and efficient photochemical reaction, DEABn should find wide applications, including in the basic and applied research areas where o-NB and its various derivatives are widely used.

References

Mar 28, 2003·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Anna Paola Pelliccioli, Jakob Wirz
Apr 9, 2004·Journal of the American Chemical Society·Yuri V Il'ichevJakob Wirz
Dec 24, 2004·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Martin GaplovskyJakob Wirz
Mar 21, 2007·Organic Letters·Pengfei WangYun Wang
Jul 24, 2008·The Journal of Organic Chemistry·Pengfei WangLurong Pan
Mar 5, 2011·The Journal of Organic Chemistry·Haishen YangPengfei Wang
May 27, 2011·The Journal of Organic Chemistry·Lei ZhouPengfei Wang
Sep 29, 2011·The Journal of Organic Chemistry·Haishen YangPengfei Wang
Nov 19, 2011·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Haishen YangPengfei Wang
Sep 12, 2013·Chemical Communications : Chem Comm·Wenya LuPengfei Wang
Feb 14, 2014·Macromolecular Rapid Communications·Ekaterina SokolovskayaJörg Lahann
Dec 19, 2014·Organic Letters·Pengfei WangZhenying Ding
May 27, 2016·The Journal of Organic Chemistry·Pengfei WangWenya Lu
Aug 12, 2016·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Alain TrachselAndreas Herrmann
Jun 24, 2017·The Journal of Organic Chemistry·Xiong Ding, Pengfei Wang
Nov 10, 2017·The Journal of Organic Chemistry·Đani ŠkalameraNikola Basarić

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Citations

Oct 5, 2019·Organic & Biomolecular Chemistry·Manoranjan BeraN D Pradeep Singh
Jul 22, 2018·The Journal of Organic Chemistry·David K RomneyChao-Jun Li

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