Study on the Chromogenic Behaviors of Oxided Anthracyl Bis(indolyl)methane

doi:10.7517/j.issn.1674-0475.2007.04.257

Abstract

Abstract: Two chromogenic compounds,oxided 2-anthracyl bis(indolyl)methane(2-AnBIM) and oxided 9-anthracyl bis(indolyl)methane(9-AnBIM) were synthesized via two steps.The medium factors(polarity,anions and pH) on the absorption behaviors of the two compounds were studied.The difference of UV behaviors in other aprotic solvents is that both 2-AnBIM and 9-AnBIM show strong red shift in CCl₄.Concentration effect and NMR data show aggregation of titled compounds could be formed at concentration of 1.0×10^-5 mol/L in CCl₄.In CH₃CN,2-AnBIM acts as a selective colorimetric sensor only for F^-,and 9-AnBIM could be sensitive for F^-,Cl^-and Ac^-.Both compounds are sensitive only for HSO₄^-in CH₃CN/H₂O(4/1) system.Both 2-AnBIM and 9-AnBIM show fluorescence emission of intermolecular charge transfer(ITC) state at 77 K.More planarity of 2-AnBIM gives longer wavelength emission and higher quantum yield compared with 9-AnBIM.No obvious emission from 2-AnBIM and 9-AnBIM at room temperature are found,the reason might be from the fast proton transfer at excited state,which decreases the conjugation degree and co-plane of molecules.

Key words: oxided anthracyl bis(indolyl)methane, hydrogen bonding, anion recognization, intramolecular charge transfer, fluorescence emission

CLC Number:

ZHANG Jun-li, WANG Hua. Study on the Chromogenic Behaviors of Oxided Anthracyl Bis(indolyl)methane[J]. Imaging Science and Photochemistry, 2007, 25(4): 257-266.

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