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Issue 21, 2011
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Dual fluorescence in 9-amino-2,7,12,17-tetraphenylporphycene

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The absorption spectrum of the asymmetric 9-amino-2,7,12,17-tetraphenylporphycene shows new, strongly red-shifted bands compared to the symmetric parental 2,7,12,17-tetraphenylporphycene and to the also asymmetric 9-acetoxy-2,7,12,17-tetraphenylporphycene. Dual emission is also observed with relative contributions that depend strongly on the excitation wavelength and temperature. The gap between the two fluorescence bands is 84 nm. Tautomerization in both the ground and excited states is shown to account for these observations, the 9-amino group being particularly able to selectively lower the energy of the first excited singlet state of just one of the trans tautomers. Introduction of amino groups in porphycenes may be a convenient way to gain a deeper insight into the tautomerization mechanisms in this macrocyclic core.

Graphical abstract: Dual fluorescence in 9-amino-2,7,12,17-tetraphenylporphycene

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Supplementary files

Article information

24 Nov 2010
31 Mar 2011
First published
26 Apr 2011

Phys. Chem. Chem. Phys., 2011,13, 10326-10332
Article type

Dual fluorescence in 9-amino-2,7,12,17-tetraphenylporphycene

M. Duran-Frigola, R. Tejedor-Estrada, D. Sánchez-García and S. Nonell, Phys. Chem. Chem. Phys., 2011, 13, 10326
DOI: 10.1039/C0CP02654A

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