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Polyethylene glycols (PEGs) are widely utilized in scientific fields (e.\u2009g., drug discovery and material sciences) as linkers and for the improvement of various properties (solubility in water, stability, etc.) of mother compounds. Therefore, deuterated PEGs can be used as novel tools for drug discovery. Although the H\/D exchange reaction (deuteration) is a powerful and straightforward method to produce deuterated compounds, the deuteration of PEGs bearing many unactivated C(sp\n                    <jats:sup>3<\/jats:sup>\n                    )\u2212H bonds has not been developed. Herein, we report the photocatalytic deuteration of multiple sites of PEGs using tetra\u2010\n                    <jats:italic>n<\/jats:italic>\n                    \u2010butylammonium decatungstate (TBADT) and D\n                    <jats:sub>2<\/jats:sub>\n                    O as an inexpensive deuterium source. This deuteration can be adapted to PEG derivatives bearing various substituents ((hetero)aryl, benzoyl, alkyl, etc.). The deuteration efficiencies of the \u03b1\u2010oxy C(sp\n                    <jats:sup>3<\/jats:sup>\n                    )\u2212H bonds at the terminal positions of the PEGs were strongly influenced by the substituents. These reactivities were elucidated by density functional theory calculations of the reaction barriers towards the formation of radical intermediates, induced by the excited state of TBADT and the PEG substrate. In addition, the applicability of deuterated PEGs to internal standard experiments and Raman spectroscopy was demonstrated.\n                  <\/jats:p>","DOI":"10.1002\/chem.202404204","type":"journal-article","created":{"date-parts":[[2024,12,23]],"date-time":"2024-12-23T11:25:31Z","timestamp":1734953131000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Photocatalytic Multiple Deuteration of Polyethylene Glycol Derivatives Using Deuterium Oxide"],"prefix":"10.1002","volume":"31","author":[{"given":"Riku","family":"Ogasahara","sequence":"first","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Osaka University  1-6 Yamada-oka, Suita Osaka 565-0871 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Miyu","family":"Mae","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Osaka University  1-6 Yamada-oka, Suita Osaka 565-0871 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