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Issue 5, 2013
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Luminescent N,O-chelated chroman-BF2 complexes: structural variants of BODIPY

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Abstract

The synthesis and characterization of 5-(chromen-4-one)-dipyrromethane (1), 5-(6-methyl-chromen-4-one)-dipyrromethane (2), 5-(6-isopropyl-chromen-4-one)-dipyrromethane (3) and the respective chromans, 7-[2-pyrrolo]-pyrrole[1,2-a]12H pyrrolino[2,3-b]chroman-4-one (4), 4-methyl-7-[2-pyrrolo]-pyrrole[1,2-a]12H pyrrolino[2,3-b]-chroman-4-one (5) and 4-isopropyl-7-[2-pyrrolo]-pyrrole[1,2-a]12H pyrrolino[2,3-b]-chroman-4-one (6) have been described. Chroman derivatives 4–6 have been used in the synthesis of highly stable, fluorescent, borondifluoride complexes (7–9). All the compounds have been fully characterised by various physicochemical techniques viz., elemental analyses, IR, HRMS, NMR (1H, 13C), electronic absorption, emission (solution and solid state), electrochemical and thermal studies. Crystal structures of dipyrromethanes 1 and 2, chroman derivative 6 and boron complexes 7–9 have been determined by X-ray single crystal analyses. Structural studies revealed that the formation of 4–6 takes place by DDQ mediated C–N coupling. The higher stability of 4–6 relative to their respective dipyrrins has been supported by theoretical studies.

Graphical abstract: Luminescent N,O-chelated chroman-BF2 complexes: structural variants of BODIPY

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Publication details

The article was received on 09 Aug 2012, accepted on 24 Oct 2012 and first published on 24 Oct 2012


Article type: Paper
DOI: 10.1039/C2DT31820B
Citation: Dalton Trans., 2013,42, 1696-1707
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    Luminescent N,O-chelated chroman-BF2 complexes: structural variants of BODIPY

    R. S. Singh, M. Yadav, R. K. Gupta, R. Pandey and D. S. Pandey, Dalton Trans., 2013, 42, 1696
    DOI: 10.1039/C2DT31820B

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