Journal
TETRAHEDRON
Volume 61, Issue 42, Pages 10073-10080Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.08.008
Keywords
substiment effect; solvatochromism; fluorescence; charge-transfer complex; metal-ion complexation
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Substituent effects on the spectroscopic properties of a solvatochromic compound, 7-methyl-2-phenylimidazo[1,2-a]pyrazin-3(7H)-one (1c), using derivatives 1 with a para-substituent R on the phenyl group, were investigated systematically. In the UV/visible absorption spectra, the solvatochromic property of I originating from hydrogen-bonding interactions was effectively regulated by the substituent effects. In particular, the cyano derivative le showed significant solvatochromism with a wide color variation range and a high sensitivity toward solvents. Similarly, the fluorescence of I showed a redshift as the electron-withdrawing property of R increased. The substituent effects were evaluated by AM1-COSMO calculations, which also suggested that derivatives 1 are good electron donors and that the electron-donating ability is regulated by R. This was confirmed by the observation of low oxidation potentials and the formation of charge-transfer complexes with tetracyanoethylene. Absorption-spectrum changes of le and le caused by metal-ion complexation were also compared, showing that the cyano derivative le is a good colorimetric sensor for the Lewis acidity of the metal ions. From these observations, it was established that para-substitution of R on the phenyl group of le caused successive modulations of the colorimetric sensor properties. (c) 2005 Elsevier Ltd. All rights reserved.
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