Synthesis and photophysical properties of 3,5-di(pyridone) and 3,5-di(oxypyridine) substituted boron-dipyrromethenes

Khan, Tamanna K. ; Rao, M. Rajeswara ; Ravikanth, M. (2010) Synthesis and photophysical properties of 3,5-di(pyridone) and 3,5-di(oxypyridine) substituted boron-dipyrromethenes European Journal of Organic Chemistry, 2010 (12). pp. 2314-2323. ISSN 1434-193X

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Official URL: http://onlinelibrary.wiley.com/wol1/doi/10.1002/ej...

Related URL: http://dx.doi.org/10.1002/ejoc.200901460

Abstract

Nucleophilic substitution reactions of 2-, 3- and 4-hydroxypyridines with 3,5-dibromo meso-aryl and meso-furyl boron-dipyrromethenes (BODIPYs) resulted in the formation of the corresponding 3,5-bis(oxopyridinyl)-BODIPYs and 3,5-bis(pyridinyloxy)-BODIPYs in decent yields. The effect of a pyridone versus an oxypyridine at the 3- and 5-positions on the spectral, electrochemical and photophysical properties were studied as a function of solvent. The 3,5-bis(oxopyridinyl)-BODIPYs exhibit broad, red-shifted absorption and emission bands, decreased quantum yields and lifetimes, displayed large Stokes shifts and easier reductions than did the 3,5-bis(pyridinyloxy)-BODIPYs. The differences in the properties of these two classes of BODIPY dyes are attributed to the extension of π-delocalization associated with the electron-deficient nature of the pyridone groups.

Item Type:Article
Source:Copyright of this article belongs to John Wiley and Sons.
Keywords:Boron; Nitrogen Heterocycles; Dyes/Pigments; Fluorescence; Fluorescent Probes; Photophysics; Nucleophilic Substitution
ID Code:104592
Deposited On:30 Nov 2017 12:30
Last Modified:30 Nov 2017 12:30

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