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Issue 16, 2019
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A controlled blue-shift in meso-nitrogen aryl fused DIPY and BODIPY skeletons

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Abstract

meso-Nitrogen substituted dipyrromethenes (DIPYs) and their boron(III) complexes (BODIPYs) were obtained by the method of nucleophilic aromatic substitution. The following intramolecular fusion with the formation of a 3H-[2,3-c]quinoline skeleton extends delocalisation, but shifts the absorption and emission hypsochromically. A further blue shift has been observed for a deprotonated form of the fused system. A nitrogen atom introduced into the system can be treated as a switching factor that controls the delocalisation significantly influencing the emission by shifting between the available amine and imine tautomeric forms.

Graphical abstract: A controlled blue-shift in meso-nitrogen aryl fused DIPY and BODIPY skeletons

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Supplementary files

Article information


Submitted
23 Feb 2019
Accepted
24 Apr 2019
First published
25 Apr 2019

Org. Chem. Front., 2019,6, 2825-2832
Article type
Research Article

A controlled blue-shift in meso-nitrogen aryl fused DIPY and BODIPY skeletons

M. Farinone, J. Cybińska and M. Pawlicki, Org. Chem. Front., 2019, 6, 2825
DOI: 10.1039/C9QO00294D

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