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Improved Photodecarboxylation Properties in Zinc Photocages Constructed using M‐nitrophenylacetic Acid Variants
Inorganic Chemistry
  • Austin K. Shigemoto, Portland State University
  • Avik Bhattacharjee, Portland State University
  • Erin E. Hickey, Worcester Polytechnic Institute
  • Hallee Jade Boyd, Worcester Polytechnic Institute
  • Theresa M. McCormick, Portland State University
  • Shawn C. Burdette, Worcester Polytechnic Institute
Document Type
Article
Publication Date
7-1-2022
Subjects
  • Photodecarboxylation -- properties
Disciplines
Abstract

The methoxy- and fluoro-derivatives of meta-nitrophenylacetic acid (mNPA) chromophores undergo photodecarboxylation with comparable quantum yields 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 quantum yield and exhibits other photophysical properties comparable to XDPAdeCage ({bis[(2-pyridyl)methyl]amino}(9-oxo-2-xanthenyl) acetic acid), the best perforiming 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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Copyright (c) 2022 The Authors

This work is licensed under a Creative Commons Attribution 4.0 International License.

Locate the Document

10.26434/chemrxiv-2021-z46wl

DOI
10.26434/chemrxiv-2021-z46wl
Persistent Identifier
https://archives.pdx.edu/ds/psu/38099
Citation Information
Shigemoto, A., Bhattacharjee, A., Hickey, E., Boyd, H., McCormick, T., & Burdette, S. (2021). Improved photodecarboxylation properties in zinc photocages constructed using m-nitrophenylacetic acid variants.