Synthesis and Characterization of Pyrrolyldipyrrin F-BODIPYs
Greening, Sarah M.
Robertsonb, Katherine N.
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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 was 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 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.
Greening, S. M., Robertson, K. N., & Thompson, A. (2018). Synthesis and characterization of pyrrolyldipyrrin F-BODIPYs. Photochemical & Photobiological Sciences, 17(1), 89-98. DOIO: 10.1039/C7PP00341B