Synthesis of naphthalimide-based indicator dyes with a 2-hydroxyethylsulfonyl function for covalent immobilisation to cellulose

A new approach for the synthesis of 2-hydroxyethylsulfonyl type indicator dyes has been introduced to the naphthalimide chemical structure. Thus, fluorescent indicator dyes can be obtained that can be covalently linked to cellulose used e.g. in optical sensor layers, textiles and wound dressings. Th...

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Bibliographic Details
Published in:Sensors and actuators. B, Chemical Chemical, 2018-12, Vol.275, p.439-445
Main Author: Mohr, Gerhard J.
Format: Article
Language:English
Subjects:
Biosensors
Cellulose
Chemosensors
Covalence
Dyes
Fluorescent indicators
Immobilization
Optical measuring instruments
Optical sensors
Organic chemistry
pH detection
Smart textiles
Synthesis
Textiles
Vinylsulfonyl dyes
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Summary:A new approach for the synthesis of 2-hydroxyethylsulfonyl type indicator dyes has been introduced to the naphthalimide chemical structure. Thus, fluorescent indicator dyes can be obtained that can be covalently linked to cellulose used e.g. in optical sensor layers, textiles and wound dressings. The approach is tailored to be simple in synthesis and with a minimum number of steps required to obtain a highly functional and stable sensor material. Three different pH indicator dyes have been prepared and covalently immobilised to transparent cellulose layers. The pKa values of the cellulose-immobilised dyes were found to be at around 3, 6 and 7, thus covering the physiologically relevant pH range. Using the 2-hydroxyethylsulfonyl group, covalent immobilisation of naphthalimides with various receptor functions may become possible.
ISSN:0925-4005
1873-3077
DOI:10.1016/j.snb.2018.07.095