Additive-free photo-mediated oxidative cyclization of pyridinium acylhydrazones to 1,3,4-oxadiazoles: solid-state conversion in a microporous organic polymer and supramolecular energy-level engineeringopen access
- Authors
- KIM, K.[KIM, KYUNGSU]; Chung, Y.K.[Chung, Y.K.]; Kim, H.[Kim, H.]; Ha, C.Y.[Ha, C.Y.]; Huh, J.[Huh, J.]; Song, C.[Song, C.]
- Issue Date
- Jan-2021
- Publisher
- Royal Society of Chemistry
- Citation
- RSC Advances, v.11, no.4, pp.1969 - 1975
- Indexed
- SCIE
SCOPUS
- Journal Title
- RSC Advances
- Volume
- 11
- Number
- 4
- Start Page
- 1969
- End Page
- 1975
- URI
- https://scholarworks.bwise.kr/skku/handle/2021.sw.skku/92316
- DOI
- 10.1039/d0ra09581h
- ISSN
- 2046-2069
- Abstract
- We discovered the efficient catalyst-free, photo-mediated oxidative cyclization reaction of bis-p-pyridinium benzoyl hydrazone (BH1) to 2-pyridinium-5-phenyl-1,3,4-oxadiazoles. This photoreaction is remarkable because it does not require additives (e.g., bases, strong oxidants, or photocatalysts), which are essential in previous reports, and proceeds very effectively even with solid-state microporous organic polymers. Interestingly, we found that the inclusion complexation of BH1 with cucurbit[7]uril (CB7) interferes with the photo-induced electron transfer from BH1 to molecular oxygen through modification of the LUMO energy level, thus inhibiting the photo-medicated oxidative cyclization. This journal is © 2021 The Royal Society of Chemistry.
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Collections - Graduate School > Chemistry > 1. Journal Articles
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