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Substituted Position Effect on Twisted intramolecular Charge Transfer of 1- and 2-anthracene aromatic Carboxamides as Chemosensors Based on Linear Polyether

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Abstract

Bi-chromophoric compounds linked to linear polyether N,N'-[oxybis(3-oxapentamethyleneoxy-2-phenyl)]- bis(1-anthracenecarboxamide) (14) and its analogues (15, 24 and 25) were synthesized. Their photochemical properties and complexation actions were investigated in acetonitrile. These fluoroionophores have shown weak emissions in the absence of guest ions, resulting in a twisted intramolecular charge transfer (TICT) quenching process (off state) of an anthracene aromatic amide moiety. After the formation of a complex with alkaline earth metal ions, a large enhancement of fluorescent intensities was obtained (on state). The efficiencies of controlling an off-on fluorescent signal using 14 and its analogues (15, 24 and 25) were larger than that of the 9-positioned analogue. These results suggested that the TICT relaxation process was effectively able to control using 14 and its analogues (15, 24 and 25) by complex formations.

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Authors and Affiliations

  1. Division of Environmental Materials Science, Graduate School of Environmental Science, Hokkaido University, 060-0810, Sapporo, Hokkaido, Japan

    Jeongsik Kim

  2. Section of Materials Science, Research Faculty of Environmental Earth Science, Hokkaido University, 060-0810, Sapporo, Hokkaido, Japan

    Tatsuya Morozumi, Hisafumi Hiraga & Hiroshi Nakamura

Authors
  1. Jeongsik Kim
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  2. Tatsuya Morozumi
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  3. Hisafumi Hiraga
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  4. Hiroshi Nakamura
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Correspondence to Hiroshi Nakamura.

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Kim, J., Morozumi, T., Hiraga, H. et al. Substituted Position Effect on Twisted intramolecular Charge Transfer of 1- and 2-anthracene aromatic Carboxamides as Chemosensors Based on Linear Polyether. ANAL. SCI. 25, 1319–1325 (2009). https://doi.org/10.2116/analsci.25.1319

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  • DOI: https://doi.org/10.2116/analsci.25.1319

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