Synthesis and properties of monodisperse oligofluorene-functionalized truxenes : highly fluorescent star-shaped architectures

A.L. Kanibolotsky, R. Berridge, P.J. Skabara, I.F. Perepichka, D.D.C. Bradley, M. Koeberg

Research output: Contribution to journalArticle

271 Citations (Scopus)

Abstract

This paper describes the strategy toward novel monodisperse, well-defined, star-shaped oligofluorenes with a central truxene core and from monofluorene to quaterfluorene arms. Introduction of solubilizing n-hexyl groups at both fluorene and truxene moieties results in highly soluble, intrinsically two-dimensional nanosized macromolecules T1-T4. The radius for the largest oligomer of ca. 3.9 nm represents one of the largest known star-shaped conjugated systems. Cyclic voltammetry experiments reveal reversible or quasi-reversible oxidation and reduction processes (E-ox = +0.74 to 0.80 V, E-red = -2.66 to 2.80 eV vs Fc/Fc(+)), demonstrating excellent electrochemical stability toward both p- and n-doping, while the band gaps of the oligomers are quite high (E-g(CV) = 3.20-3.40 eV). Close band gaps of 3.05-3.29 eV have been estimated from the electron absorption spectra. These star-shaped macromolecules demonstrate good thermal stability (up to 400-420 degreesC) and improved glass transition temperatures with an increase in length of the oligofluorene arms (from T-g = 63 degreesC for T1 to 116 degreesC for T4) and show very efficient blue photoluminescence (lambda(PL) = 398-422 nm) in both solution (Phi(PL) = 70-86%) and solid state (PhiPL = 43-60%). Spectroelectrochernical experiments reveal that compounds T1-T4 are stable electrochromic systems which change their color reversibly from colorless in the neutral state (similar to340-400 nm) to colored (from red to purple color; similar to500-600 nm) in the oxidized state.
LanguageEnglish
Pages13695-13702
Number of pages7
JournalJournal of the American Chemical Society
Volume126
Issue number42
DOIs
Publication statusPublished - 2004

Fingerprint

Stars
Color
Macromolecules
Oligomers
Transition Temperature
Photoluminescence
Energy gap
Electron absorption
Oxidation-Reduction
Glass
Hot Temperature
Electrons
Cyclic voltammetry
Absorption spectra
Thermodynamic stability
Experiments
Doping (additives)
Oxidation
fluorene
Glass transition temperature

Keywords

  • light-emitting-diodes
  • discotic liquid-crystals
  • field-effect transistors
  • phenylboronic acid
  • deuterium nmr
  • blue emission
  • derivatives
  • phase
  • copolymers
  • alignment

Cite this

Kanibolotsky, A. L., Berridge, R., Skabara, P. J., Perepichka, I. F., Bradley, D. D. C., & Koeberg, M. (2004). Synthesis and properties of monodisperse oligofluorene-functionalized truxenes : highly fluorescent star-shaped architectures. Journal of the American Chemical Society, 126(42), 13695-13702. https://doi.org/10.1021/ja039228n
Kanibolotsky, A.L. ; Berridge, R. ; Skabara, P.J. ; Perepichka, I.F. ; Bradley, D.D.C. ; Koeberg, M. / Synthesis and properties of monodisperse oligofluorene-functionalized truxenes : highly fluorescent star-shaped architectures. In: Journal of the American Chemical Society. 2004 ; Vol. 126, No. 42. pp. 13695-13702.
@article{005e832ae6e44e958baf5338f375b125,
title = "Synthesis and properties of monodisperse oligofluorene-functionalized truxenes : highly fluorescent star-shaped architectures",
abstract = "This paper describes the strategy toward novel monodisperse, well-defined, star-shaped oligofluorenes with a central truxene core and from monofluorene to quaterfluorene arms. Introduction of solubilizing n-hexyl groups at both fluorene and truxene moieties results in highly soluble, intrinsically two-dimensional nanosized macromolecules T1-T4. The radius for the largest oligomer of ca. 3.9 nm represents one of the largest known star-shaped conjugated systems. Cyclic voltammetry experiments reveal reversible or quasi-reversible oxidation and reduction processes (E-ox = +0.74 to 0.80 V, E-red = -2.66 to 2.80 eV vs Fc/Fc(+)), demonstrating excellent electrochemical stability toward both p- and n-doping, while the band gaps of the oligomers are quite high (E-g(CV) = 3.20-3.40 eV). Close band gaps of 3.05-3.29 eV have been estimated from the electron absorption spectra. These star-shaped macromolecules demonstrate good thermal stability (up to 400-420 degreesC) and improved glass transition temperatures with an increase in length of the oligofluorene arms (from T-g = 63 degreesC for T1 to 116 degreesC for T4) and show very efficient blue photoluminescence (lambda(PL) = 398-422 nm) in both solution (Phi(PL) = 70-86{\%}) and solid state (PhiPL = 43-60{\%}). Spectroelectrochernical experiments reveal that compounds T1-T4 are stable electrochromic systems which change their color reversibly from colorless in the neutral state (similar to340-400 nm) to colored (from red to purple color; similar to500-600 nm) in the oxidized state.",
keywords = "light-emitting-diodes, discotic liquid-crystals, field-effect transistors, phenylboronic acid, deuterium nmr, blue emission, derivatives, phase, copolymers, alignment",
author = "A.L. Kanibolotsky and R. Berridge and P.J. Skabara and I.F. Perepichka and D.D.C. Bradley and M. Koeberg",
year = "2004",
doi = "10.1021/ja039228n",
language = "English",
volume = "126",
pages = "13695--13702",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "42",

}

Kanibolotsky, AL, Berridge, R, Skabara, PJ, Perepichka, IF, Bradley, DDC & Koeberg, M 2004, 'Synthesis and properties of monodisperse oligofluorene-functionalized truxenes : highly fluorescent star-shaped architectures' Journal of the American Chemical Society, vol. 126, no. 42, pp. 13695-13702. https://doi.org/10.1021/ja039228n

Synthesis and properties of monodisperse oligofluorene-functionalized truxenes : highly fluorescent star-shaped architectures. / Kanibolotsky, A.L.; Berridge, R.; Skabara, P.J.; Perepichka, I.F.; Bradley, D.D.C.; Koeberg, M.

In: Journal of the American Chemical Society, Vol. 126, No. 42, 2004, p. 13695-13702.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and properties of monodisperse oligofluorene-functionalized truxenes : highly fluorescent star-shaped architectures

AU - Kanibolotsky, A.L.

AU - Berridge, R.

AU - Skabara, P.J.

AU - Perepichka, I.F.

AU - Bradley, D.D.C.

AU - Koeberg, M.

PY - 2004

Y1 - 2004

N2 - This paper describes the strategy toward novel monodisperse, well-defined, star-shaped oligofluorenes with a central truxene core and from monofluorene to quaterfluorene arms. Introduction of solubilizing n-hexyl groups at both fluorene and truxene moieties results in highly soluble, intrinsically two-dimensional nanosized macromolecules T1-T4. The radius for the largest oligomer of ca. 3.9 nm represents one of the largest known star-shaped conjugated systems. Cyclic voltammetry experiments reveal reversible or quasi-reversible oxidation and reduction processes (E-ox = +0.74 to 0.80 V, E-red = -2.66 to 2.80 eV vs Fc/Fc(+)), demonstrating excellent electrochemical stability toward both p- and n-doping, while the band gaps of the oligomers are quite high (E-g(CV) = 3.20-3.40 eV). Close band gaps of 3.05-3.29 eV have been estimated from the electron absorption spectra. These star-shaped macromolecules demonstrate good thermal stability (up to 400-420 degreesC) and improved glass transition temperatures with an increase in length of the oligofluorene arms (from T-g = 63 degreesC for T1 to 116 degreesC for T4) and show very efficient blue photoluminescence (lambda(PL) = 398-422 nm) in both solution (Phi(PL) = 70-86%) and solid state (PhiPL = 43-60%). Spectroelectrochernical experiments reveal that compounds T1-T4 are stable electrochromic systems which change their color reversibly from colorless in the neutral state (similar to340-400 nm) to colored (from red to purple color; similar to500-600 nm) in the oxidized state.

AB - This paper describes the strategy toward novel monodisperse, well-defined, star-shaped oligofluorenes with a central truxene core and from monofluorene to quaterfluorene arms. Introduction of solubilizing n-hexyl groups at both fluorene and truxene moieties results in highly soluble, intrinsically two-dimensional nanosized macromolecules T1-T4. The radius for the largest oligomer of ca. 3.9 nm represents one of the largest known star-shaped conjugated systems. Cyclic voltammetry experiments reveal reversible or quasi-reversible oxidation and reduction processes (E-ox = +0.74 to 0.80 V, E-red = -2.66 to 2.80 eV vs Fc/Fc(+)), demonstrating excellent electrochemical stability toward both p- and n-doping, while the band gaps of the oligomers are quite high (E-g(CV) = 3.20-3.40 eV). Close band gaps of 3.05-3.29 eV have been estimated from the electron absorption spectra. These star-shaped macromolecules demonstrate good thermal stability (up to 400-420 degreesC) and improved glass transition temperatures with an increase in length of the oligofluorene arms (from T-g = 63 degreesC for T1 to 116 degreesC for T4) and show very efficient blue photoluminescence (lambda(PL) = 398-422 nm) in both solution (Phi(PL) = 70-86%) and solid state (PhiPL = 43-60%). Spectroelectrochernical experiments reveal that compounds T1-T4 are stable electrochromic systems which change their color reversibly from colorless in the neutral state (similar to340-400 nm) to colored (from red to purple color; similar to500-600 nm) in the oxidized state.

KW - light-emitting-diodes

KW - discotic liquid-crystals

KW - field-effect transistors

KW - phenylboronic acid

KW - deuterium nmr

KW - blue emission

KW - derivatives

KW - phase

KW - copolymers

KW - alignment

UR - http://pubs.acs.org/cgi-bin/article.cgi/jacsat/2004/126/i42/pdf/ja039228n.pdf

UR - http://dx.doi.org/10.1021/ja039228n

U2 - 10.1021/ja039228n

DO - 10.1021/ja039228n

M3 - Article

VL - 126

SP - 13695

EP - 13702

JO - Journal of the American Chemical Society

T2 - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 42

ER -