Singlet Oxygen Generation from Polyaminoglycerol by Spin-Flip-Based Electron Transfer

Jung Seung Nam, Youngjoo Hong, Chae Gyu Lee, Tae In Kim, Chaiheon Lee, Deok Ho Roh, In Seong Lee, Songa Kweon, Gyunhyeok Ahn, Seung Kyu Min, Byeong Su Kim, Tae Hyuk Kwon

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)


Reactive oxygen species have drawn attention owing to their strong oxidation ability. In particular, the singlet oxygen (1O2) produced by energy transfer is the predominant species for controlling oxidation reactions efficiently. However, conventional 1O2generators, which rely on enhanced energy transfer, frequently suffer from poor solubility, low stability, and low biocompatibility. Herein, we introduce a hyperbranched aliphatic polyaminoglycerol (hPAG) as a 1O2generator, which relies on spin-flip-based electron transfer. The coexistence of a lone pair electron on the nitrogen atom and a hydrogen-bonding donor (the protonated form of nitrogen and hydroxyl group) affords proximity between hPAG and O2. Subsequent direct electron transfer after photo-irradiation induces hPAG•+-O2•-formation, and the following spin-flip process generates 1O2. The spin-flip-based electron transfer pathway is analyzed by a series of photophysical, electrochemical, and computational studies. The 1O2generator, hPAG, is successfully employed in photodynamic therapy and as an antimicrobial reagent.

Original languageEnglish
Pages (from-to)933-942
Number of pages10
JournalJACS Au
Issue number4
Publication statusPublished - 2022 Apr 25

Bibliographical note

Funding Information:
This work was supported by the Ulsan National Institute of Science & Technology (UNIST) (Research Fund 1.220026.01), and the National Research Foundation of Korea (NRF) (Grant 2016M1A2A2940910, 2017M3A7B4052802, 2017R1A2B3012148, 2018R1A5A1025208, 2019R1A2C1007744, 2021M3H4A1A0305139011, 2021R1A2C3004978, and 2021R1A2C2009504). C.G.L. and I.S.L. acknowledge support from the Global Ph.D. Fellowship Program through the NRF funded by the Ministry of Education (NRF-2018H1A2A1061237 and NRF-2017H1A2A1043792).

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

All Science Journal Classification (ASJC) codes

  • Chemistry (miscellaneous)
  • Analytical Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry


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