Abstract
A new water-soluble pyrene-containing fluorescent polymer, 1-{3′-S-[poly(acryloyl ethylene diamine hydrochloride)-2′-methyl propionic acid]}propionyloxy hexyloxy pyrene (P3) with defined structure, was designed and synthesized using the click reaction between thiol and a carbon-carbon double bond. The intermediate products P1 (S-1-dodecyl-S′-[poly(N-Boc-acryloyl ethylene diamine)-2′-methyl propionic acid]trithiocarbonate) and AHP (1-(acryloyloxy hexyloxy)pyrene) were prepared via reversible addition fragmentation chain transfer (RAFT) polymerization and Williamson synthesis, respectively. Conjugating AHP with P1, P2 (1-{3′-S-[poly(N-butoxycarbonyl-acryloyl ethylene diamine)-2″-methyl propionic acid]} propionyloxy hexyloxy pyrene) was synthesized, adopting both the reduction reaction of a trithioester bond of P1 to thiol and the click reaction between thiol and the carbon-carbon double bond of AHP simultaneously. P3 was obtained by the deprotection of the resulting Boc-protected polymer (P2) with aqueous HCl. The experiment results showed that P2 exhibited a bright blue-violet emission band at approximately 387–429 nm. After deprotection, P3 displayed good solubility in water and not only exhibited a blue-violet fluorescence emission band at approximately 387–429 nm in aqueous solution but also had the similar photoluminescent spectra to those of AHP and P2 in dichloromethane. The fluorescence quantum yields of P2 in dilute tetrahydrofuran and P3 in a dilute aqueous solution were 0.44 and 0.39, respectively. This experiment provided a novel insight into the study of water-soluble fluorescent polymers.
Highlights
Water-soluble fluorescent polymers have drawn much attention in recent years given their successful utility in distinguishing different proteins [1] and isozymes [2], as an effective and sensitive probe for further bio-applications differentiating tumorous and malignant cells [3,4], ranging from cytotoxicity studies to pharmacodiagnosis
Water solubility is a prerequisite of those fluorescent polymers for applications in biological environments [5,6], since as long as the fluorescent polymers enjoy water solubility they can be uniformly dispersed in the aqueous medium of the system under characterization
Chemical modification method that was the designed strategy in this contribution, which was chemically bonded to the fluorescent dye on the polymer chain or born hydrophilic groups to fluorescent polymers
Summary
Water-soluble fluorescent polymers have drawn much attention in recent years given their successful utility in distinguishing different proteins [1] and isozymes [2], as an effective and sensitive probe for further bio-applications differentiating tumorous and malignant cells [3,4], ranging from cytotoxicity studies to pharmacodiagnosis. The water-soluble fluorescent polymers in the field of applied biotechnology research exhibited unique advantages. Since S–H bonds are relatively weak, thiol groups are subject to rapid oxidation during purification and storage and, thereby, result in the low conversion in the following click reaction. To circumvent this limitation, the synthesis of thiol groups and click reaction were simultaneously performed in one system (one-pot method). Polymers 2015, 7, 2625–2637 how the pyrenyl functional end group is introduced into a water-soluble polymer, which is applied to the light emitting properties of pyrene in aqueous solution. Water-soluble pyrene-containing fluorescent polymer (P3) was obtained by the deprotection of the resulting Boc-protected polymer (P2). The fluorescent polymer P3 had good water solubility and showed good optical performance
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