Issue 7, 2007

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

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

Article information

Article type
Paper
Submitted
10 Jan 2007
Accepted
01 Feb 2007
First published
15 Feb 2007

Org. Biomol. Chem., 2007,5, 1056-1061

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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