Several advanced optical oxygen sensor materials are
presented. They are based on bright NIR-emitting platinum(II)–benzoporphyrins covalently
incorporated into a variety of polymeric matrices.
The dye–polymer conjugates are prepared either via Suzuki coupling of the brominated
porphyrins to the styrene backbone or via
co-polymerisation of the monomers with monostyryl porphyrin derivative.
Importantly, in both strategies a highly stable C–C bond is obtained. The
resulted materials benefit from excellent photophysical properties of the
benzoporphyrin dyes (high brightness, emission in the NIR part of the spectrum)
and high stability of the covalently grafted materials due to complete
suppression of dye migration and leaching.
This is demonstrated to be particularly important for
operation of the sensors in harsh conditions e.g.
during steam sterilization where the materials based on non-covalently grafted
dyes showed significant drift of their calibration.
Additionally, we present a new synthetic method for
preparation of analytically pure benzoporphyrins via simple 1-step template condensation which a promising
alternative to the commonly used Lindsey method.
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