The synthesis and properties of solution processable phenyl cored thiophene dendrimers

William J. Mitchell, Nikos Kopidakis, Gary Rumbles, David S. Ginley, Scan E. Shaheen

Research output: Contribution to journalArticle

77 Citations (Scopus)

Abstract

In this paper we describe the convergent synthesis of a new class of phenyl cored thiophene dendrimers, which are promising candidates for use in organic semiconductor devices. We have prepared dendrimers with three and four dendrons around the core as well as dendrimers with 1st and 2nd generation dendrons. All the dendrimers were soluble in common organic solvents such as chloroform, THF and toluene. The structures and size properties are confirmed by a number of techniques including NMR, GPC and MALDI-TOF-MS. Decomposition was studied by TGA with initial breakdown of the hexyl surface groups followed by the aromatic core. The spectroscopic properties were studied by UV-vis and PL spectrometry which demonstrated substantial differences between the dendrimers with three and four dendrons. Optical band gaps varied between 2.34 and 2.60 eV for thin films of the dendrimers and electronic band gaps were, on average, 0.3 eV greater than the optical band gaps. The smallest band gap was measured for the dendrimer with four 2nd generation dendrons around the phenyl core. Fluorescence lifetimes of the molecules in solution ranged from 200 to 560 ps. This range in values was attributed to differences in internal conversion rates associated with varying degrees of flexibility of the extended dendrons.

Original languageEnglish
Pages (from-to)4518-4528
Number of pages11
JournalJournal of Materials Chemistry
Volume15
Issue number42
DOIs
Publication statusPublished - Nov 14 2005

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Dendrimers
Thiophenes
dendrimers
Thiophene
thiophenes
synthesis
Optical band gaps
Energy gap
Semiconducting organic compounds
internal conversion
organic semiconductors
Semiconductor devices
Chlorine compounds
chloroform
semiconductor devices
Organic solvents
Spectrometry
Toluene
toluene
flexibility

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Materials Science(all)

Cite this

The synthesis and properties of solution processable phenyl cored thiophene dendrimers. / Mitchell, William J.; Kopidakis, Nikos; Rumbles, Gary; Ginley, David S.; Shaheen, Scan E.

In: Journal of Materials Chemistry, Vol. 15, No. 42, 14.11.2005, p. 4518-4528.

Research output: Contribution to journalArticle

Mitchell, William J. ; Kopidakis, Nikos ; Rumbles, Gary ; Ginley, David S. ; Shaheen, Scan E. / The synthesis and properties of solution processable phenyl cored thiophene dendrimers. In: Journal of Materials Chemistry. 2005 ; Vol. 15, No. 42. pp. 4518-4528.
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