Journal
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
Volume 78, Issue 2, Pages 726-731Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.saa.2010.12.004
Keywords
Anion receptor; Indolylmethane; Nitro-substitution; Deprotonation; Oxidation process
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Funding
- National Natural Science Foundation of China [20672121]
- State Key Laboratory of Oxo Synthesis & Selective Oxidation [OSSO2008kjk6]
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A series of nitro-substituted 3,3'-bis-indolyl phenylmethane derivatives were synthesized and their anion binding properties were investigated in detail. The introduction of the electron-withdrawing nitro group into indole unit and/or meso-phenyl ring, which leads to the increased acidity of indole NH and meso-position CH proton, has a positive effect on anion binding. The nitro-substituted bis(indolyl)methane receptors exhibited selective colorimetric sensing of F- anion, as revealed by the notable color and spectral changes, rationally due to the deprotonation of the indole NH of the receptor. Meanwhile, the additive introduction of the nitro substituents on the meso-phenyl ring of bis(indolyl)methane can lead to the deprotonation of the meso-position CH and further induce an irreversible oxidation process obtaining bis(indolyl)methene product in the F- anion sensing system. (C) 2010 Elsevier B.V. All rights reserved.
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