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

TETRAHEDRON

卷:67

Article

Kim, Jeongsik^1,2  Oka, Yoshikazu²  Morozumi, Tatsuya³  Choi, Eun Wha⁴  Nakamura, Hiroshi³ 

[1] Korea Res Inst Chem Technol, Adv Mat Div, Taejon 305606, South Korea

[2] Hokkaido Univ, Grad Sch Environm Sci, Div Environm Earth Sci, Sapporo, Hokkaido 0600810, Japan

[3] Hokkaido Univ, Res Fac Environm Earth Sci, Sapporo, Hokkaido 0600810, Japan

[4] Korea Res Inst Chem Technol, Drug Discovery Div, Taejon 305606, South Korea

关键词: Photoinduced electron transfer;    Anthracene;    Steric effect;    Chemosensor;    Benzo-15-crown-5;   

DOI  :  10.1016/j.tet.2011.05.042

来源: Elsevier

【 摘 要 】

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 H-1 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 pi-conjugation between the amide moiety and the benzene ring. (C) 2011 Elsevier Ltd. All rights reserved.

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