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3-/3,5-Pyrrole-substituted BODIPY derivatives and their photophysical and electrochemical studies

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Abstract

Nucleophilic substitution on 3-bromo/3,5-dibromo-4,4′-difluoro-8-(aryl)-4-bora-3a,4a-diaza-s-indacene (BODIPY), substituted with anisyl or thienyl at meso positions, with neat pyrrole afforded the mono and di-pyrrole substituted BODIPYs 1–4 in good yields. Large bathochromic shifts, upto ∼180 nm in absorption maxima (581–682 nm), and fluorescence maxima (606–695 nm) were observed for these BODIPYs. Absorption and fluorescence properties were studied in different solvents to compare the effect of mono and di substitution on BODIPY. The Lippert-Mataga equations were used which predict strong polarization of mono substituted BODIPYs. Electrochemical studies were carried out to find the oxidation potential and HOMO energy levels were calculated. Theoretical studies of 1–4 provide the insight on the electron density distribution in 1–4. Theoretical and experimental photo-physical studies in different solvents were correlated to find the substituent effects on BODIPY.

Mono-pyrrole substituted BODIPYs show enhanced charge-transfer behavior compared to unsubstituted and bis-pyrrole substituted BODIPY as inferred from photophysical, electrochemical and DFT studies.

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Acknowledgements

KKJ, AN and Sanoj thank DST Inspire scholarships. Partial funding was provided by Department of Science and Technology, India (SR/FT/CS-87/2010). We also thank Tata Institute of Fundamental Research, Mumbai for providing the NMR, MALDI-TOF and TCSPC facilities.

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Author notes

  1. KARTHIKA J KADASSERY

    Present address: Department of Chemistry, University at Buffalo, Buffalo, NY, 14260, USA

  2. SANOJ RAJ

    Present address: Department of Chemistry, University of Illinois at Chicago, Chicago, Illinois, 60607, USA

Authors and Affiliations

  1. UM-DAE, Centre for Excellence in Basic Sciences, Health center building, Kalina campus, Santacruz (E), Mumbai, 400 098, India

    KARTHIKA J KADASSERY, AKANKSHA NIMESH, SANOJ RAJ & NEERAJ AGARWAL

  2. Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India

    AKANKSHA NIMESH

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  1. KARTHIKA J KADASSERY
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Supplementary information (SI)

Supplementary data of absorption and emission spectra, and CV data of BODIPY derivatives 1–4 in different solvents are available at www.ias.ac.in/chemsci.

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KADASSERY, K.J., NIMESH, A., RAJ, S. et al. 3-/3,5-Pyrrole-substituted BODIPY derivatives and their photophysical and electrochemical studies. J Chem Sci 128, 1435–1443 (2016). https://doi.org/10.1007/s12039-016-1134-9

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