Synthesis and characterization of an amphiphilic blue-light-emitting glycosylated poly(naphthalene/phenylene) copolymer

Miklós Nagy, Dávid Rácz, L. Daróczi, Balázs Lukács, I. Jóna, M. Zsuga, S. Kéki

Research output: Article

3 Citations (Scopus)

Abstract

A glucosylated naphthalene/phenylene-type copolymer was prepared by the Suzuki polycondensation of 1,6- dibromo-2-naphthyl-tetra-O-acetyl-b-D-glucoside and benzene- 1,4-diboronic acid. In the first step, poly[2-(tetra- Oacetylglucopyranosyl)- 1,6-naphthalene-1,4-phenylene] was obtained, which was deacetylated to obtain poly(2- glucopyranosyl-1,6-naphthalene-1,4-phenylene). The polymerwas characterized by GPC and 1H NMR spectroscopy. It was found that the glucosylated copolymer was soluble in polar solvents such as a methanol/THF mixture and even in water. The poly[2-(tetra-O-acetylglucopyranosyl)-1,6- naphthalene-1,4-phenylene] showed self-assembly behavior in themethanol/ THFmixture and in aqueousmedium. The formation of uniform-sized nanospheres in the solid phase having an average diameter of 460nm was detected by TEM. The nanospheres showed blue fluorescence under optical microscopy. It was shown that the copolymer formedaggregates also inaqueousmedium.Usingdynamic light scattering, the cmc and hydrodynamic radius of the aggregates were determined. The fluorescence properties of the copolymer were also studied. Emission spectra were recorded and the emission maxima were determined. lmax=396nm was found for poly[2-(tetra-O-acetylglucopyranosyl)- 1,6-naphthalene-1,4-phenylene] and lmax=403-405nm was found for poly(2-glucopyranosyl- 1,6-naphthalene-1,4- phenylene), depending on the solvent applied. The emission maximum and the shape of the emission peak showed solvent dependence that can be attributed to the self assembly of the copolymer. It was shown that the red shift and the broader emission peak can be attributed to a specific p-interaction between the polymer chains due to self-assembly. In short, the elevated solubility, the ability of the preparation of well-defined surfaces through self-assembly and the ability to alter the emission spectrum make this glucosylated copolymer a promising candidate in the field of blue-light-emitting polymers.

Original languageEnglish
Pages (from-to)1891-1899
Number of pages9
JournalMacromolecular Chemistry and Physics
Volume212
Issue number17
DOIs
Publication statusPublished - szept. 1 2011

Fingerprint

Naphthalene
naphthalene
copolymers
Copolymers
Self assembly
self assembly
synthesis
Nanospheres
Polymers
emission spectra
Fluorescence
fluorescence
glucosides
Glucosides
polymers
Polycondensation
Benzene
red shift
Light scattering
Nuclear magnetic resonance spectroscopy

ASJC Scopus subject areas

  • Materials Chemistry
  • Polymers and Plastics
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Condensed Matter Physics

Cite this

@article{d3790625e4574ad780abbdd8b3531083,
title = "Synthesis and characterization of an amphiphilic blue-light-emitting glycosylated poly(naphthalene/phenylene) copolymer",
abstract = "A glucosylated naphthalene/phenylene-type copolymer was prepared by the Suzuki polycondensation of 1,6- dibromo-2-naphthyl-tetra-O-acetyl-b-D-glucoside and benzene- 1,4-diboronic acid. In the first step, poly[2-(tetra- Oacetylglucopyranosyl)- 1,6-naphthalene-1,4-phenylene] was obtained, which was deacetylated to obtain poly(2- glucopyranosyl-1,6-naphthalene-1,4-phenylene). The polymerwas characterized by GPC and 1H NMR spectroscopy. It was found that the glucosylated copolymer was soluble in polar solvents such as a methanol/THF mixture and even in water. The poly[2-(tetra-O-acetylglucopyranosyl)-1,6- naphthalene-1,4-phenylene] showed self-assembly behavior in themethanol/ THFmixture and in aqueousmedium. The formation of uniform-sized nanospheres in the solid phase having an average diameter of 460nm was detected by TEM. The nanospheres showed blue fluorescence under optical microscopy. It was shown that the copolymer formedaggregates also inaqueousmedium.Usingdynamic light scattering, the cmc and hydrodynamic radius of the aggregates were determined. The fluorescence properties of the copolymer were also studied. Emission spectra were recorded and the emission maxima were determined. lmax=396nm was found for poly[2-(tetra-O-acetylglucopyranosyl)- 1,6-naphthalene-1,4-phenylene] and lmax=403-405nm was found for poly(2-glucopyranosyl- 1,6-naphthalene-1,4- phenylene), depending on the solvent applied. The emission maximum and the shape of the emission peak showed solvent dependence that can be attributed to the self assembly of the copolymer. It was shown that the red shift and the broader emission peak can be attributed to a specific p-interaction between the polymer chains due to self-assembly. In short, the elevated solubility, the ability of the preparation of well-defined surfaces through self-assembly and the ability to alter the emission spectrum make this glucosylated copolymer a promising candidate in the field of blue-light-emitting polymers.",
keywords = "Glucose, Light emission, Nanoparticles, Naphthalene, Self assembly",
author = "Mikl{\'o}s Nagy and D{\'a}vid R{\'a}cz and L. Dar{\'o}czi and Bal{\'a}zs Luk{\'a}cs and I. J{\'o}na and M. Zsuga and S. K{\'e}ki",
year = "2011",
month = "9",
day = "1",
doi = "10.1002/macp.201100091",
language = "English",
volume = "212",
pages = "1891--1899",
journal = "Macromolecular Chemistry and Physics",
issn = "1022-1352",
publisher = "Wiley-VCH Verlag",
number = "17",

}

TY - JOUR

T1 - Synthesis and characterization of an amphiphilic blue-light-emitting glycosylated poly(naphthalene/phenylene) copolymer

AU - Nagy, Miklós

AU - Rácz, Dávid

AU - Daróczi, L.

AU - Lukács, Balázs

AU - Jóna, I.

AU - Zsuga, M.

AU - Kéki, S.

PY - 2011/9/1

Y1 - 2011/9/1

N2 - A glucosylated naphthalene/phenylene-type copolymer was prepared by the Suzuki polycondensation of 1,6- dibromo-2-naphthyl-tetra-O-acetyl-b-D-glucoside and benzene- 1,4-diboronic acid. In the first step, poly[2-(tetra- Oacetylglucopyranosyl)- 1,6-naphthalene-1,4-phenylene] was obtained, which was deacetylated to obtain poly(2- glucopyranosyl-1,6-naphthalene-1,4-phenylene). The polymerwas characterized by GPC and 1H NMR spectroscopy. It was found that the glucosylated copolymer was soluble in polar solvents such as a methanol/THF mixture and even in water. The poly[2-(tetra-O-acetylglucopyranosyl)-1,6- naphthalene-1,4-phenylene] showed self-assembly behavior in themethanol/ THFmixture and in aqueousmedium. The formation of uniform-sized nanospheres in the solid phase having an average diameter of 460nm was detected by TEM. The nanospheres showed blue fluorescence under optical microscopy. It was shown that the copolymer formedaggregates also inaqueousmedium.Usingdynamic light scattering, the cmc and hydrodynamic radius of the aggregates were determined. The fluorescence properties of the copolymer were also studied. Emission spectra were recorded and the emission maxima were determined. lmax=396nm was found for poly[2-(tetra-O-acetylglucopyranosyl)- 1,6-naphthalene-1,4-phenylene] and lmax=403-405nm was found for poly(2-glucopyranosyl- 1,6-naphthalene-1,4- phenylene), depending on the solvent applied. The emission maximum and the shape of the emission peak showed solvent dependence that can be attributed to the self assembly of the copolymer. It was shown that the red shift and the broader emission peak can be attributed to a specific p-interaction between the polymer chains due to self-assembly. In short, the elevated solubility, the ability of the preparation of well-defined surfaces through self-assembly and the ability to alter the emission spectrum make this glucosylated copolymer a promising candidate in the field of blue-light-emitting polymers.

AB - A glucosylated naphthalene/phenylene-type copolymer was prepared by the Suzuki polycondensation of 1,6- dibromo-2-naphthyl-tetra-O-acetyl-b-D-glucoside and benzene- 1,4-diboronic acid. In the first step, poly[2-(tetra- Oacetylglucopyranosyl)- 1,6-naphthalene-1,4-phenylene] was obtained, which was deacetylated to obtain poly(2- glucopyranosyl-1,6-naphthalene-1,4-phenylene). The polymerwas characterized by GPC and 1H NMR spectroscopy. It was found that the glucosylated copolymer was soluble in polar solvents such as a methanol/THF mixture and even in water. The poly[2-(tetra-O-acetylglucopyranosyl)-1,6- naphthalene-1,4-phenylene] showed self-assembly behavior in themethanol/ THFmixture and in aqueousmedium. The formation of uniform-sized nanospheres in the solid phase having an average diameter of 460nm was detected by TEM. The nanospheres showed blue fluorescence under optical microscopy. It was shown that the copolymer formedaggregates also inaqueousmedium.Usingdynamic light scattering, the cmc and hydrodynamic radius of the aggregates were determined. The fluorescence properties of the copolymer were also studied. Emission spectra were recorded and the emission maxima were determined. lmax=396nm was found for poly[2-(tetra-O-acetylglucopyranosyl)- 1,6-naphthalene-1,4-phenylene] and lmax=403-405nm was found for poly(2-glucopyranosyl- 1,6-naphthalene-1,4- phenylene), depending on the solvent applied. The emission maximum and the shape of the emission peak showed solvent dependence that can be attributed to the self assembly of the copolymer. It was shown that the red shift and the broader emission peak can be attributed to a specific p-interaction between the polymer chains due to self-assembly. In short, the elevated solubility, the ability of the preparation of well-defined surfaces through self-assembly and the ability to alter the emission spectrum make this glucosylated copolymer a promising candidate in the field of blue-light-emitting polymers.

KW - Glucose

KW - Light emission

KW - Nanoparticles

KW - Naphthalene

KW - Self assembly

UR - http://www.scopus.com/inward/record.url?scp=84855666548&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84855666548&partnerID=8YFLogxK

U2 - 10.1002/macp.201100091

DO - 10.1002/macp.201100091

M3 - Article

AN - SCOPUS:84855666548

VL - 212

SP - 1891

EP - 1899

JO - Macromolecular Chemistry and Physics

JF - Macromolecular Chemistry and Physics

SN - 1022-1352

IS - 17

ER -