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Steric effects on controlling of photoinduced electron transfer action of anthracene modified benzo-15-crown-5 by complexation with Mg2+ and Ca2+

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Title: Steric effects on controlling of photoinduced electron transfer action of anthracene modified benzo-15-crown-5 by complexation with Mg2+ and Ca2+
Authors: Kim, Jeongsik Browse this author
Oka, Yoshikazu Browse this author
Morozumi, Tatsuya Browse this author
Choi, Eun Wha Browse this author
Nakamura, Hiroshi Browse this author
Keywords: Photoinduced electron transfer
Anthracene
Steric effect
Chemosensor
Benzo-15-crown-5
Issue Date: 1-Jul-2011
Publisher: Elsevier Ltd
Journal Title: Tetrahedron
Volume: 67
Issue: 26
Start Page: 4814
End Page: 4819
Publisher DOI: 10.1016/j.tet.2011.05.042
Abstract: Benzo-crown ether based chemosensors linked by an amide bond at the 1-, 2- or 9-positions of anthracene rings were synthesized. Their complexation behavior with alkaline earth metal ions in acetonitrile was investigated using fluorescence, UV, and 1H-NMR spectroscopy. In the absence of a metal ion, all compounds showed only very slight fluorescence emissions (fluorescence ‘off’ state) because of intramolecular charge/electron transfer process. After the complex formation with Mg2+ and Ca2+, however, only the 2-position analogue gave a fluorescence ‘on’ response by inhibiting the photoinduced electron transfer. Because 2- positioned anthracene was free from steric hindrance of the crown ether ring, a strongly bent complex structure was formed with Mg2+ and Ca2+, which induced a breakdown of π- conjugation between the amide moiety and the benzene ring.
Relation: http://www.sciencedirect.com/science/journal/00404020
Type: article (author version)
URI: http://hdl.handle.net/2115/46902
Appears in Collections:環境科学院・地球環境科学研究院 (Graduate School of Environmental Science / Faculty of Environmental Earth Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 中村 博

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