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A Modular Approach Towards Fluorescent pH and Ascorbic Acid Probes Based on Ring‐Opening Metathesis Polymerization
Author(s) -
Gallas Katharina,
Knall AstridCaroline,
Scheicher Sylvia R.,
Fast David E.,
Saf Robert,
Slugovc Christian
Publication year - 2014
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201300561
Subject(s) - polymerization , copolymer , monomer , norbornene , chemistry , fluorophore , romp , polymer chemistry , moiety , ascorbic acid , metathesis , ring opening metathesis polymerisation , polymer , fluorescence , amine gas treating , combinatorial chemistry , organic chemistry , physics , food science , quantum mechanics
Copolymerization represents a modular synthetic strategy toward optochemical sensors by disassembling small molecule probes and recombining them to screen various fluorophore‐quencher combinations, instead of synthesizing individual sensor molecules. To demonstrate this, a polymerizable, fluorescent 1,6,7,12‐tetrachloroperylene‐3,4:9,10‐bis(dicarboximide) derivative with a norbornene ester side chain is prepared and copolymerized with a tertiary‐amine‐bearing monomer, as well as an oligo‐glycol‐bearing monomer, via ring‐opening metathesis polymerization (ROMP). In this manner, water‐soluble optical pH sensor polymers (with apparent p k a values of 6.4–7) are obtained. The effect of the macromolecular architecture on the sensing performance is evaluated, whereby a diblock copolymer structure made of an oligoglycol segment and a segment containing the secondary amine and the fluorescent moiety is identified as being most favorable for pH sensing. Similarly, profluorescent polymers are obtained by employing nitroxides instead of secondary amines, which allows detection of ascorbic acid (with a detection limit of 0.1 × 10 −3 m ) in water.