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Issue 7, 2007
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Synthesis and near-infrared luminescence of a deuterated conjugated porphyrin dimer for probing the mechanism of non-radiative deactivation

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Abstract

β,meso,β-Fused porphyrin oligomers have many attractive photophysical features such as strong absorption in the near-IR at wavelengths greater than 1000 nm, and high two-photon cross sections. However their ultrafast S1–S0 deactivation (kd > 1011 s−1) limits potential applications. We have synthesised a deuterated fused porphyrin dimer to test whether deuteration influences the rate of non-radiative deactivation. An efficient synthetic strategy was developed, starting with deuteration of dipyrromethane. Deuteration of the zinc porphyrin dimer does not affect its fluorescence quantum yield in CD2Cl2 (ΦfD/ΦfH = 1.00 ± 0.05). This implies that the ultrafast non-radiative deactivation is not simply a consequence of the small S1–S0 energy gap. Comparison with other conjugated porphyrin oligomers confirms that the deactivation rate in the edge-fused oligomers is faster than would be expected from the energy gap law. This result indicates that it should be possible to create near-IR dyes with similar S1–S0 energy gaps to the β,meso,β-fused porphyrin oligomers but with slower rates of S1–S0 decay.

Graphical abstract: Synthesis and near-infrared luminescence of a deuterated conjugated porphyrin dimer for probing the mechanism of non-radiative deactivation

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Publication details

The article was received on 10 Jan 2007, accepted on 01 Feb 2007 and first published on 15 Feb 2007


Article type: Paper
DOI: 10.1039/B700408G
Citation: Org. Biomol. Chem., 2007,5, 1056-1061
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    Synthesis and near-infrared luminescence of a deuterated conjugated porphyrin dimer for probing the mechanism of non-radiative deactivation

    M. J. Frampton, G. Accorsi, N. Armaroli, J. E. Rogers, P. A. Fleitz, K. J. McEwan and H. L. Anderson, Org. Biomol. Chem., 2007, 5, 1056
    DOI: 10.1039/B700408G

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