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Issue 26, 2014
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Time-resolved fluorescence spectroscopy study of excited state dynamics of alkyl- and benzo-substituted triphyrin(2.1.1)

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Abstract

We have investigated the photophysical properties of alkyl-substituted triphyrin(2.1.1) (ATp) and benzotriphyrin(2.1.1) (BTp) by steady-state and time-resolved fluorescence spectroscopy. We focused on the effect of NH proton tautomerization, planarity of the macrocycles, and substituents on these properties. The fluorescence quantum yields (Φy) of ATp did not depend on solvent viscosity, whereas those of BTp increased with solvent viscosity, reaching a maximum value of 0.17 in paraffin. Interestingly, analyzing Φy showed that the non-radiative rate constant of BTp decreased sharply as the solvent viscosity increased. These results suggest that the substituted phenyl groups play a crucial role in suppressing molecular distortion, thus leading to decreased non-radiative relaxation in triphyrin(2.1.1). The hydrogen bond formed in the inner cavity potentially contributes to the suppression of the structural distortion, whereas the pyrrole rings in the macrocycle are close, as in porphycene.

Graphical abstract: Time-resolved fluorescence spectroscopy study of excited state dynamics of alkyl- and benzo-substituted triphyrin(2.1.1)

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Article information


Submitted
20 Jan 2014
Accepted
09 Apr 2014
First published
10 Apr 2014

Phys. Chem. Chem. Phys., 2014,16, 13129-13135
Article type
Paper
Author version available

Time-resolved fluorescence spectroscopy study of excited state dynamics of alkyl- and benzo-substituted triphyrin(2.1.1)

Y. Iima, D. Kuzuhara, Z. Xue, S. Akimoto, H. Yamada and K. Tominaga, Phys. Chem. Chem. Phys., 2014, 16, 13129
DOI: 10.1039/C4CP00301B

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