Preparation of the Water-Soluble Pyrene-Containing Fluorescent Polymer by One-Pot Method

Abstract

A new water-soluble pyrene-containing fluorescent polymer, 1-{3 1-S-[poly(acryloyl ethylene diamine hydrochloride)-2 1-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 1-[poly(N-Boc-acryloyl ethylene diamine)-2 1-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 1-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.

Recyclable Thermoresponsive Polymer−β-Glucosidase Conjugate with Intact Hydrolysis Activity

“…The enzyme modification by DMP-CTA was studied through UV−vis spectroscopy (Figure 2). Native B8CYA8 showed absorbance at 280 nm (Figure 2), but after modification with DMP-CTA, an additional peak at nearly 310 nm indicated the presence of a CS double bond of trithiocarbonate group of DMP-CTA 49,50 and confirmed the formation of B8CYA8-macroCTA. Although the excess DMP-CTA was removed by dialysis, free enzyme was present in the solution in addition to the B8CYA8-macroCTA.…”

Supramolecular Luminescent Sensors

“…Biologically relevant detection applications tend to occur in aqueous environments, which require that the polymers be soluble in such environments . Methods to impart aqueous solubility include the incorporation of charged moieties to generate conjugated polyelectrolytes or the incorporation of polar, charge-neutral side chains (vide supra) .…”

“…Biologically relevant detection applications tend to occur in aqueous environments, 1631 which require that the polymers be soluble in such environments. 1632 Methods to impart aqueous solubility include the incorporation of charged moieties to generate conjugated polyelectrolytes or the incorporation of polar, charge-neutral side chains (vide supra). 1633 However, in some cases water-insoluble polymers can be used for detection in aqueous environments, such as in conjugated polymer thin film sensors that were dipped into an analyte-containing aqueous solution and respond to the presence of that analyte with a change in spectral signal.…”

Amphiphilic water soluble cationic ring opening metathesis copolymer as an antibacterial agent

“…Di‐ tert ‐butyl dicarbonate (BOC) and triethylamine were purchased from Sigma‐Aldrich and ethylenediamine (EDA) was purchased from Carlo Erba Reagents. Mono BOC protection ethylene diamine (EDA‐BOC) was synthesized in the laboratory by a standard method as previously described . Exo‐3a,4,7,7a‐tetrahydro‐4,7‐epoxyisobenzofuran‐1,3‐dione (1) was synthesized from maleic anhydride and furan in THF solvent by Diels–Alder reaction according to a published article .…”