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Published on: April 1, 2013
Tris-benzo[cd]indole Cyanine Enables the NIR-photosensitized Radical and Thiol-ene Polymerizations at 940 nm
Christine Elian1, Benjamin Mourot2, Camil Benbouziyane2
1Institut de Chimie et des Matériaux Paris-Est, UMR-CNRS 7182-UPEC, 2-8 rue Henri Dunant, 94320, Thiais, France.
Abstract:
A near-infrared-absorbing heptamethine (HM+ ) incorporating three bulky benzo[cd]indole heterocycles was designed to efficiently prevent self-aggregation of the dye, which results in a strong enhancement of its photoinitiating reactivity as compared to a parent bis-benzo[cd]indole heptamethine (HMCl+ ) used as a reference system. In this context, we highlight an efficient free-radical NIR-polymerization up to a 100 % acrylates C=C bonds conversion even under air conditions. Such an important initiating performance was obtained by incorporating our NIR-sensitizer into a three-component system leading to its self-regeneration. This original photoredox cycle was thoroughly investigated through the identification of each intermediary species using EPR spectroscopy.
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