Highly emissive supramolecular oligo(p-phenylene vinylene) dendrimers

F.S. Precup, J.C. Garcia-Martinez, A.P.H.J. Schenning, E.W. Meijer

Research output: Contribution to journalArticleAcademicpeer-review

57 Citations (Scopus)

Abstract

p-Conjugated oligo(p-phenylene vinylene) (OPV) guest mols. for interaction with dendritic hosts were synthesized and fully characterized by NMR spectroscopy, MALDI-TOF-MS, elemental anal. and optical measurements. The binding properties of the five different OPV guests to a N,N-bis[(3-adamantyl ureido) propyl] methylamine host have been investigated. The guests that contained an aryl urea glycine spacer were bound with the highest assocn. const. Subsequently, an adamantyl urea modified fifth generation poly(propylene imine) dendrimer was synthesized as a multivalent host which contains 32 N,N-bis[(3-adamantyl ureido) propyl] amine binding sites. Size exclusion chromatog. showed that 32 of the OPV guests strongly bind to the fifth generation adamantyl functionalized dendritic host. In the case of the supramol. dendritic host/guest system smooth homogeneous thin films could be obtained by spin coating. The dendritic guest-host complexes showed a significantly higher emission upon binding then that of the individual mols. due to the three-dimensional orientation of the OPV guest mols. In the solid state, this enhancement in luminescence was a factor of 10. The p-conjugated oligomers are less aggregated in the supramol. assemblies presumably because of a shielding effect of the bulky adamantyl units present in the hosts. [on SciFinder (R)]
Original languageEnglish
Pages (from-to)12953-12960
JournalJournal of the American Chemical Society
Volume125
Issue number42
DOIs
Publication statusPublished - 2003

Fingerprint

Dendrimers
Urea
Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry
Spin coating
Binding sites
Luminescence
Oligomers
Shielding
Glycine
Nuclear magnetic resonance spectroscopy
Amines
Amino acids
Polypropylenes
Magnetic Resonance Spectroscopy
Binding Sites
Thin films
oligo(p-phenylene vinylene)
methylamine
poly(propyleneimine)

Cite this

@article{99452e84ebea446ca4f887736e90b062,
title = "Highly emissive supramolecular oligo(p-phenylene vinylene) dendrimers",
abstract = "p-Conjugated oligo(p-phenylene vinylene) (OPV) guest mols. for interaction with dendritic hosts were synthesized and fully characterized by NMR spectroscopy, MALDI-TOF-MS, elemental anal. and optical measurements. The binding properties of the five different OPV guests to a N,N-bis[(3-adamantyl ureido) propyl] methylamine host have been investigated. The guests that contained an aryl urea glycine spacer were bound with the highest assocn. const. Subsequently, an adamantyl urea modified fifth generation poly(propylene imine) dendrimer was synthesized as a multivalent host which contains 32 N,N-bis[(3-adamantyl ureido) propyl] amine binding sites. Size exclusion chromatog. showed that 32 of the OPV guests strongly bind to the fifth generation adamantyl functionalized dendritic host. In the case of the supramol. dendritic host/guest system smooth homogeneous thin films could be obtained by spin coating. The dendritic guest-host complexes showed a significantly higher emission upon binding then that of the individual mols. due to the three-dimensional orientation of the OPV guest mols. In the solid state, this enhancement in luminescence was a factor of 10. The p-conjugated oligomers are less aggregated in the supramol. assemblies presumably because of a shielding effect of the bulky adamantyl units present in the hosts. [on SciFinder (R)]",
author = "F.S. Precup and J.C. Garcia-Martinez and A.P.H.J. Schenning and E.W. Meijer",
year = "2003",
doi = "10.1021/ja0211050",
language = "English",
volume = "125",
pages = "12953--12960",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "42",

}

Highly emissive supramolecular oligo(p-phenylene vinylene) dendrimers. / Precup, F.S.; Garcia-Martinez, J.C.; Schenning, A.P.H.J.; Meijer, E.W.

In: Journal of the American Chemical Society, Vol. 125, No. 42, 2003, p. 12953-12960.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Highly emissive supramolecular oligo(p-phenylene vinylene) dendrimers

AU - Precup, F.S.

AU - Garcia-Martinez, J.C.

AU - Schenning, A.P.H.J.

AU - Meijer, E.W.

PY - 2003

Y1 - 2003

N2 - p-Conjugated oligo(p-phenylene vinylene) (OPV) guest mols. for interaction with dendritic hosts were synthesized and fully characterized by NMR spectroscopy, MALDI-TOF-MS, elemental anal. and optical measurements. The binding properties of the five different OPV guests to a N,N-bis[(3-adamantyl ureido) propyl] methylamine host have been investigated. The guests that contained an aryl urea glycine spacer were bound with the highest assocn. const. Subsequently, an adamantyl urea modified fifth generation poly(propylene imine) dendrimer was synthesized as a multivalent host which contains 32 N,N-bis[(3-adamantyl ureido) propyl] amine binding sites. Size exclusion chromatog. showed that 32 of the OPV guests strongly bind to the fifth generation adamantyl functionalized dendritic host. In the case of the supramol. dendritic host/guest system smooth homogeneous thin films could be obtained by spin coating. The dendritic guest-host complexes showed a significantly higher emission upon binding then that of the individual mols. due to the three-dimensional orientation of the OPV guest mols. In the solid state, this enhancement in luminescence was a factor of 10. The p-conjugated oligomers are less aggregated in the supramol. assemblies presumably because of a shielding effect of the bulky adamantyl units present in the hosts. [on SciFinder (R)]

AB - p-Conjugated oligo(p-phenylene vinylene) (OPV) guest mols. for interaction with dendritic hosts were synthesized and fully characterized by NMR spectroscopy, MALDI-TOF-MS, elemental anal. and optical measurements. The binding properties of the five different OPV guests to a N,N-bis[(3-adamantyl ureido) propyl] methylamine host have been investigated. The guests that contained an aryl urea glycine spacer were bound with the highest assocn. const. Subsequently, an adamantyl urea modified fifth generation poly(propylene imine) dendrimer was synthesized as a multivalent host which contains 32 N,N-bis[(3-adamantyl ureido) propyl] amine binding sites. Size exclusion chromatog. showed that 32 of the OPV guests strongly bind to the fifth generation adamantyl functionalized dendritic host. In the case of the supramol. dendritic host/guest system smooth homogeneous thin films could be obtained by spin coating. The dendritic guest-host complexes showed a significantly higher emission upon binding then that of the individual mols. due to the three-dimensional orientation of the OPV guest mols. In the solid state, this enhancement in luminescence was a factor of 10. The p-conjugated oligomers are less aggregated in the supramol. assemblies presumably because of a shielding effect of the bulky adamantyl units present in the hosts. [on SciFinder (R)]

U2 - 10.1021/ja0211050

DO - 10.1021/ja0211050

M3 - Article

C2 - 14558844

VL - 125

SP - 12953

EP - 12960

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 42

ER -