Photophysics and electrochemistry of a platinum-acetylide disubstituted perylenediimide

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Llewellyn, Ben A. ; Slater, Anna G. ; Goretzki, Gudrun ; Easun, Timothy ; Sun, Xue-Zhong ; Davies, E. Stephen ; Argent, Stephen P. ; Lewis, William ; Beeby, Andrew ; George, Michael W. ; Champness, Neil R. (2014)
  • Publisher: Royal Society of Chemistry
  • Related identifiers: doi: 10.1039/c3dt50874a
  • Subject: QD
    arxiv: Physics::Atomic and Molecular Clusters

The synthesis and photophysical study of a perylene diimide (PDI) functionalised with platinum acetylide units of the type, trans{–C[triple bond, length as m-dash]C–Pt(PBu3)2–C[triple bond, length as m-dash]C–Ph} and comparison with a phenylacetylide substituted model compound are reported. The model compound demonstrates typical perylene absorption and photoluminescence spectra characteristic of singlet excited state formation and decay. The Pt-substitution, however, appears to induce spin–orbit coupling into the chromophore and giving rise to a triplet excited state which was confirmed by transient absorption measurements. This excited state is quenched by oxygen, leading to the formation of singlet oxygen in dichloromethane, recorded by time-resolved near-infrared luminescence measurements.
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    40 Figure 1. Views of a) the single crystal structure of N,N'-di-(cyclohexyl)- 1,7-di(tri-isopropyl-silylethynyl)-PDI, note the 1,7-isomeric arrangement; b) pairs of π-π stacked M and P isomers of N,N'-di-(cyclohexyl)-1,7- di(tri-isopropyl-silylethynyl)-PDI. Carbon - grey, nitrogen - blue, oxygen - red, silicon - yellow. Hydrogen atoms are omitted for clarity.

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