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Journal of Fluorescence

, Volume 26, Issue 3, pp 845–854 | Cite as

Impact of Structural Modification on the Photophysical Response of Benzoquinoline Fluorophores

  • Pronab Kundu
  • Saptarshi Ghosh
  • Rajiv Karmakar
  • Gourhari Maiti
  • Nitin Chattopadhyay
ORIGINAL ARTICLE

Abstract

Structural influence on the photophysical behavior of two pairs of molecular systems from the biologically potent benzoquinoline family, namely, dimethyl-3-(4-chlorophenyl)-3,4-dihydrobenzo[f]-quinoline-1,2-dicarboxylate, dimethyl-3-(2,6-dichlorophenyl)-3,4-dihydrobenzo[f]quinoline-1,2-dicarboxylate and their corresponding dehydrogenated analogues has been investigated exploiting experimental as well as computational techniques. The study unveils that dehydrogenation in the heterocyclic rings of the studied quinoline derivatives modifies their photophysics radically. Experimental observations imply that the photophysical behavior of the dihydro analogues is governed by the intramolecular charge transfer (ICT) process. However, the ICT process is restricted significantly by the dehydrogenation of the heterocyclic rings. Computational exertion leads to the proposition that the change in the electronic distribution in these molecular systems on dehydrogenation is the rationale behind the dramatic modification of their photophysics.

Keywords

Benzoquinoline Photophysics Intramolecular charge transfer Dehydrogenation Charge distribution 

Notes

Acknowledgments

Financial support from the Council of Scientific and Industrial Research, Government of India (Project No. 01/(2807)/14/EMR-II), is gratefully acknowledged. P.K. and S.G. thank Council of Scientific and Industrial Research and University Grants Commission respectively for their research fellowships.

Supplementary material

10895_2016_1772_MOESM1_ESM.doc (3 mb)
ESM 1 (DOC 3069 kb)

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Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Pronab Kundu
    • 1
  • Saptarshi Ghosh
    • 1
  • Rajiv Karmakar
    • 1
  • Gourhari Maiti
    • 1
  • Nitin Chattopadhyay
    • 1
  1. 1.Department of ChemistryJadavpur UniversityKolkataIndia

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