Solid polymer substrates and coated fibers containing 2,4,6-trinitrobenzene motifs as smart labels for the visual detection of biogenic amine vapors.
Attempts to polymerize trinitrobenzene derivatives (TNB) have been fruitless so far. Accordingly, polymers containing TNB have not been exploited in spite of their envisaged potential applications. Here, we describe two ways for preparing polymers with TNB moieties thus overcoming the previously reported polymerization impairments. We also report on the exploitation of the materials, both obtained as tractable transparent films and coated fibers, as smart labels for the visual detection of amine vapors. More precisely, amines in the atmosphere surrounding the sensory materials diffuse into them reacting with the TNB motifs forming highly colored Meisenheimer complexes, giving rise to development of color and to the naked eye sensing phenomenon. This is the case of highly volatile amines, such as trimethylamine, produced in food spoilage, specifically in the deterioration of fish or meat, for which the color development of the smart labels can be used as a visual test for food freshness.
Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Plaza de Misael Bañuelos s/n, 09001 Burgos (Spain). jlpablos@ubu.es.
Jesús L
JL
Pablos
Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Plaza de Misael Bañuelos s/n, 09001 Burgos (Spain).
Saúl
S
Vallejos
Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Plaza de Misael Bañuelos s/n, 09001 Burgos (Spain).
Asunción
A
Muñoz
Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Plaza de Misael Bañuelos s/n, 09001 Burgos (Spain).
María J
MJ
Rojo
Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Plaza de Misael Bañuelos s/n, 09001 Burgos (Spain).
Felipe
F
Serna
Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Plaza de Misael Bañuelos s/n, 09001 Burgos (Spain).
Félix C
FC
García
Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Plaza de Misael Bañuelos s/n, 09001 Burgos (Spain). jmiguel@ubu.es.
José M
JM
García
D001679:Biogenic Amines / Q000737:chemistry*; D018857:Food Packaging / Q000592:standards*; D011108:Polymers / Q000737:chemistry; D014301:Trinitrobenzenes / Q000737:chemistry*
D001679:Biogenic Amines; D011108:Polymers; D014301:Trinitrobenzenes; C029222:sym-trinitrobenzene
amine sensors; biogenic amines; chemosensors; packaged food; polymers