Tris‐benzoindole Cyanine Enables the NIR‐photosensitized Radical and Thiol‐ene Polymerizations at 940 nm

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+...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2023-10, Vol.62 (43)
Main Authors: Elian, Christine, Mourot, Benjamin, Benbouziyane, Camil, Jean‐Pierre Malval, Lajnef, Sonia, Peyrot, Fabienne, Massuyeau, Florian, Siri, Olivier, Jacquemin, Denis, Simon, Pascal, Davy‐Louis Versace
Format: Article
Language:English
Subjects:
Acrylates
Near infrared radiation
Polymerization
Reference systems
Spectroscopy
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Summary: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.In memory of Professor Yusuf Yağci
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202305963