Synthesis and Characterization of New Xanthene Derivatives, and Their Electrochemical Study

This work investigated the synthesis of biphenyl-3,3′,4,4′-tetracarboxylic dianhydride and benzophenone-3,3′,4,4′-tetracarboxylic dianhydride derivatives (3a–e and 6a–e) with different substituted phenols via Friedel-Crafts acylation reaction in the presence of dilute sulfuric acid. Dianhydride derivatives with 3-N,N′-dimethylamino phenol (3d and 6d) and resorcinol (3e and 6e) have been found to be highly fluorescent. The structures of all newly synthesized compounds were confirmed by the chromatographic, spectral and elemental data. Electrochemical study was done to determine to band gap energy, LUMO and HOMO levels energy. Band gap and LUMO energy levels were found to be lowest in xanthene derivatives substituted with 3-N,N′-dimethylamino group having value 2.24 and 4.85 eV respectively.

[1]  Richard J. Fitzmaurice,et al.  Photodetachment spectra of deprotonated fluorescent protein chromophore anions. , 2012, The journal of physical chemistry. A.

[2]  Y. Na.  Recent cancer drug development with xanthone structures , 2009 .

[3]  Bernd Engels,et al.  Exciton trapping in pi-conjugated materials: a quantum-chemistry-based protocol applied to perylene bisimide dye aggregates. , 2008, Journal of the American Chemical Society.

[4]  B. Bhowmik,et al.  Photophysics of xanthene dyes in surfactant solution. , 2005, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[5]  P. Marshall.  Rules for the visible absorption spectra of halogenated Fluorescein dyes , 1975, The Histochemical Journal.

[6]  A. Jha,et al.  Convenient synthesis of 12H-benzo[a]xanthenes from 2-tetralone , 2004 .

[7]  G. Feijoo,et al.  A packed-bed fungal bioreactor for the continuous decolourisation of azo-dyes (Orange II). , 2001, Journal of biotechnology.

[8]  S. Diele,et al.  Fluorescent J-type aggregates and thermotropic columnar mesophases of perylene bisimide dyes. , 2001, Chemistry.

[9]  A. Clayton,et al.  Spectral Properties of Fluorescein in Solvent‐Water Mixtures: Applications as a Probe of Hydrogen Bonding Environments in Biological Systems , 1998, Photochemistry and photobiology.

[10]  R. Ion,et al.  The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption and emission spectroscopy. , 1998, Acta biochimica Polonica.

[11]  C. Tsai,et al.  Potentiation of the antiviral activity of poly r(A-U) by xanthene dyes. , 1990, Cell biology international reports.

[12]  C. Knight,et al.  Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles. , 1989, The Biochemical journal.