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Impact of Structural Modification on the Photophysical Response of Benzoquinoline Fluorophores

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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.

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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.

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Authors and Affiliations

  1. Department of Chemistry, Jadavpur University, Kolkata, 700 032, India

    Pronab Kundu, Saptarshi Ghosh, Rajiv Karmakar, Gourhari Maiti & Nitin Chattopadhyay

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  1. Pronab Kundu
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  2. Saptarshi Ghosh
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  3. Rajiv Karmakar
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  4. Gourhari Maiti
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  5. Nitin Chattopadhyay
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Correspondence to Nitin Chattopadhyay.

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Highlights

• Structural impact on the photophysics of synthesized benzoquinolines is studied• Drastic modification in the photophysics results upon dehydrogenation• Dihydrobenzoquinolines give dual emissions for the normal and the ICT species• The ICT species is formed in the ground as well as in the photoexcited states • Dehydrogenation in the heterocyclic ring leads to suppression of the ICT emission

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Kundu, P., Ghosh, S., Karmakar, R. et al. Impact of Structural Modification on the Photophysical Response of Benzoquinoline Fluorophores. J Fluoresc 26, 845–854 (2016). https://doi.org/10.1007/s10895-016-1772-9

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