Journal of Fluorescence

, Volume 25, Issue 6, pp 1645–1654 | Cite as

Synthesis, Fluorescence Spectra, Redox Property and the DNA Binding Studies of 7-phenylacenaphtho[1,2-b]quinoxalin-7-ium chloride: Evidences of the Formation of Neutral Radical Analogue

  • Suman Kundu
  • Ananya Banerjee
  • Arpan De
  • Asma Yasmeen Khan
  • Gopinatha Suresh Kumar
  • Ranjan Bhadra
  • Prasanta Ghosh
ORIGINAL ARTICLE

Abstract

Reaction of acenaphthoquinone with N-phenyl-o-phenylenediamine in methanol in presence of HCl yielded 7-phenylacenaphtho[1,2-b]quinoxalin-7-ium chloride, [1][Cl]. [1][Cl] is brightly fluorescencent in dichloromethane (λex = 403 nm and λem = 442, 464, 488 nm) and water (λex = 408 nm and λem = 545 nm). Density functional theory (DFT) and time dependent (TD) DFT calculations on [1]+ at the B3LYP level of the theory elucidated that the origin of the lower energy excitation at around 400 nm is due to π → π* transition. [1]+ is redox active and exhibits a reversible cathodic wave at −0.66 V referenced to Fc+/Fc couple due to [1]+/[1] redox couple. Electrogenerated neutral radical analogue [1] was characterized by electron paramagnetic resonance (EPR), UV–vis spectra and DFT calculations. DNA binding studies using the techniques of UV–vis absorption, fluorescence, circular dichroism (CD) spectra, viscosity, gel electrophoresis, hydrodynamic, isothermal titration calorimetry (ITC) and UV optical melting studies of [1][Cl] revealed that [1]+ is a strong DNA intercalator obeying neighbor exclusion principle. ITC experiment authenticated that the binding of [1]+ to DNA is entropy driven.

Keywords

7-phenylacenaphtho[1,2-b]quinoxalin-7-ium chloride 7-phenylacenaphtho[1,2-b]quinoxalin radical DNA intercalator Biophysical studies 

Supplementary material

10895_2015_1651_MOESM1_ESM.doc (92 kb)
ESM 1Electronic absorption spectra of [1]+ obtained from TD DFT calculations (Fig. S1), Excitation energies, oscillator strengths, transition types and dominant contributions of UV–vis absorption bands of [1]+ obtained from TD DFT calculations (Table S1) and the coordinates of the optimized geometries of the [1]+ and [1] (Tables S2 and S3). (DOC 91 kb)

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Suman Kundu
    • 1
  • Ananya Banerjee
    • 2
  • Arpan De
    • 2
  • Asma Yasmeen Khan
    • 3
  • Gopinatha Suresh Kumar
    • 3
  • Ranjan Bhadra
    • 1
  • Prasanta Ghosh
    • 1
  1. 1.Department of ChemistryR. K. M. Residential CollegeKolkataIndia
  2. 2.VJRC R&D Center, Vijaygarh Jyotish Ray CollegeKolkataIndia
  3. 3.Biophysical Chemistry Laboratory, Organic and Medicinal Chemistry DivisionCSIR-Indian Institute of Chemical BiologyKolkataIndia

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