Next Article in Journal
Metathesis Polymerization Reactions Induced by the Bimetallic Complex (Ph4P)2[W2(μ-Br)3Br6]
Previous Article in Journal
Study of the Tensile Properties of CFRP Strengthened Steel Plates
Article Menu

Export Article

Open AccessArticle
Polymers 2015, 7(12), 2625-2637; doi:10.3390/polym7121538

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

College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Shin-ichi Yusa
Received: 22 September 2015 / Revised: 21 November 2015 / Accepted: 4 December 2015 / Published: 9 December 2015
View Full-Text   |   Download PDF [5681 KB, uploaded 9 December 2015]   |  

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. View Full-Text
Keywords: pyrene; water-soluble fluorescent polymer; click-chemistry; thiol-ene reaction; reversible addition-fragmentation chain transfer (RAFT) pyrene; water-soluble fluorescent polymer; click-chemistry; thiol-ene reaction; reversible addition-fragmentation chain transfer (RAFT)
Figures

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Li, X.; Wang, M.; Tan, H.; Yang, Q.; Wang, A.; Bai, L.; Zhao, H.; Wu, Y. Preparation of the Water-Soluble Pyrene-Containing Fluorescent Polymer by One-Pot Method. Polymers 2015, 7, 2625-2637.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Polymers EISSN 2073-4360 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top