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Synthesis and characterization of pyrrolyldipyrrin F-BODIPYs

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Abstract

A series of synthetic analogs of the tripyrrolic natural product prodigiosin were complexed with boron trifluoride to generate the corresponding F-BODIPYs. The maximum wavelengths of absorption and emission of the pyrrolyldipyrrin F-BODIPYs were tuned through variation of the substituents about the pyrrolyldipyrrinato core. The limited variation of substituents on the C-ring did not significantly affect absorption and emission. However, variation of substituents on the B-ring and A-ring resulted in a corresponding red-shift in absorption and emission reaching maximum wavelengths of 600 nm. The presence of electron donating substituents on the B-ring caused a decrease in the Stokes shift, while the presence of electron-withdrawing substituents caused an increase, ranging from 3–25 nm. Stokes shifts were solvent-dependant for some compounds. The inclusion of a dimethylamino group resulted in photo-induced electron transfer and thus quenched fluorescence which was restored upon protonation.

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Acknowledgments

We thank Dr Estelle Marchal for preparation of pyrrolyldipyrrin HCl salts, Pankaj Subedi for assistance with obtaining fluorescence spectra and Dr Norman Schepp for spectrofluorometer access.

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Authors and Affiliations

  1. Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4J3, Canada

    Sarah M. Greening & Alison Thompson

  2. Department of Chemistry, Saint Mary’s University, Halifax, NS, B3H 3C3, Canada

    Katherine N. Robertson

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  1. Sarah M. Greening
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Correspondence to Alison Thompson.

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Greening, S.M., Robertson, K.N. & Thompson, A. Synthesis and characterization of pyrrolyldipyrrin F-BODIPYs. Photochem Photobiol Sci 17, 89–98 (2018). https://doi.org/10.1039/c7pp00341b

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  • DOI: https://doi.org/10.1039/c7pp00341b

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