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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/128/09/1435-1443

    • Keywords

       

      BODIPY; charge transfer; lippert-mataga equation; solvatochromism.

    • Abstract

       

      Nucleophilic substitution on 3-bromo/3,5-dibromo-4,4'-difluoro-8-(aryl)-4-bora-3a,4a-diaza-sindacene (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 monosubstituted 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 findthe substituent effects on BODIPY.

    • Author Affiliations

       

      KARTHIKA J KADASSERY1 2 AKANKSHA NIMESH1 3 SANOJ RAJ1 4 NEERAJ AGARWAL1

      1. UM-DAE, Centre for Excellence in Basic Sciences, Health center building, Kalina campus, Santacruz (E), Mumbai, 400 098 India
      2. Current address: Department of Chemistry, University at Buffalo, Buffalo, NY 14260, USA
      3. Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016 India
      4. Current address: Department of Chemistry, University of Illinois at Chicago, Chicago, Illinois 60607, USA
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