Synthesis of an amphiphilic rhodamine derivative and characterization of its solution and thin film properties

Hagit Aviv, Sivan Harazi, Dillon Schiff, Yoni Ramon, Yaakov R. Tischler

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Here we present characterization of solution and thin film properties of Lissamine rhodamine B sulfonyl didodecyl amine (LRSD), an amphiphilic derivative of rhodamine. LRSD was synthesized by functionalizing Lissamine rhodamine B sulfonyl chloride (LRSC) with didodecylamine via a straightforward sulfonylation reaction. LRSD's long alkane chains make it highly soluble in chloroform, with a marked increase in brightness compared to the starting material. LRSD is shown to form well-defined robust micelles in water, without the addition of a co-surfactant and stable monolayers at the air-water interface. The greater lipophilicity of LRSD also enables doping into non-polar polymeric host matrices such as polystyrene with less aggregation and hence higher fluorescence quantum yield than LRSC or even rhodamine B. The monolayers of LRSD were prepared via Langmuir-Blodgett deposition and showed shifts in the photoluminescence peak from 575 nm to 595 nm, as the surface pressure is varied from 3 mN/m to 11 mN/m.

Original languageEnglish
Pages (from-to)86-91
Number of pages6
JournalThin Solid Films
Volume564
DOIs
StatePublished - 1 Aug 2014

Bibliographical note

Funding Information:
This research was supported by the ISF (Israeli Science Foundation ), grant number: 206738 .

Keywords

  • Dopant
  • Dye
  • Langmuir-Blodgett
  • Micelle
  • Monolayer
  • Photoluminescence

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