Jump to main content
Jump to site search

Issue 1, 2018
Previous Article Next Article

Synthesis and characterization of pyrrolyldipyrrin F-BODIPYs

Author affiliations

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.

Graphical abstract: Synthesis and characterization of pyrrolyldipyrrin F-BODIPYs

Back to tab navigation

Supplementary files

Publication details

The article was received on 08 Sep 2017, accepted on 27 Nov 2017 and first published on 08 Dec 2017


Article type: Paper
DOI: 10.1039/C7PP00341B
Citation: Photochem. Photobiol. Sci., 2018,17, 89-98
  •   Request permissions

    Synthesis and characterization of pyrrolyldipyrrin F-BODIPYs

    S. M. Greening, K. N. Robertson and A. Thompson, Photochem. Photobiol. Sci., 2018, 17, 89
    DOI: 10.1039/C7PP00341B

Search articles by author

Spotlight

Advertisements