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Improved Photodecarboxylation Properties in Zinc Photocages Constructed Using m‐Nitrophenylacetic Acid Variants

Von Wiley-VCH zur Verfügung gestellt

DPAdeCageOMe is a new photocaged complex for Zn2+ that utilizes a photodecarboxylation reaction of a meta-nitrophenylacetic acid derivative. DPAdeCageOMe exhibits a 104-fold change in affinity for Zn2+ upon photolysis which occurs at wavelengths and with quantum yields near to xanthone chromophores owing to the addition of the methoxy group.


Abstract

The methoxy- and fluoro-derivatives of meta-nitrophenylacetic acid (mNPA) chromophores undergo photodecarboxylation with comparable quantum yields (Φ) to unsubstituted mNPA, but uncage at red-shifted excitation wavelengths. This observation prompted us to investigate DPAdeCageOMe (2-[bis(pyridin-2-ylmethyl)amino]-2-(4-methoxy-3-nitrophenyl)acetic acid) and DPAdeCageF (2-[bis(pyridin-2-ylmethyl)amino]-2-(4-fluoro-3-nitrophenyl)acetic acid) as Zn2+ photocages. DPAdeCageOMe has a high Φ and exhibits other photophysical properties comparable to XDPAdeCage ({bis[(2-pyridyl)methyl]amino}(9-oxo-2-xanthenyl) acetic acid), the best preforming Zn2+ photocage reported to date. Since the synthesis of DPAdeCageOMe is more straightforward than XDPACage, the new photocage will be a highly competitive tool for biological applications.

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