Synthesis and characterization of a J-aggregating TDBC derivative in solution and in Langmuir-Blodgett films

Hagit Aviv, Yaakov R. Tischler

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

Here we present the synthesis and optical characterization of a new amphiphilic cyanine dye, 1,1′-dioctadecane-3,3′-di(4-sulfobutyl)-5,5′,6,6′-tetrachloro-benzimidazolocarbo-cyanine (C18S4). C18S4 is a derivative of the heavily studied J-aggregating cyanine dye TDBC that was designed specifically for creating stable amphiphilic monolayers when spread at an air-water interface. Unlike TDBC, which readily J-aggregates in water, we show that C18S4 introduced into water tends to produce micelles with monomeric spectral properties and only exhibits strong J-aggregation after an emulsification procedure and a week of dye reorganization. When deposited on a Langmuir Blodgett (LB) trough, C18S4 forms a stable monolayer with a repeatable isotherm. Layers transferred via LB deposition to a functionalized glass substrate show pronounced J-aggregation, depending on the surface transfer pressure. Layers transferred at 35 mN/m present an intense narrow absorption spectrum peaked at λ=589 nm with FWHM=523 cm-1 (18 nm). The accompanying fluorescence shows a narrow spectrum with FWHM=332 cm-1 (11.5 nm) and a Stokes shift less than 1 nm. The ability to create J-aggregates of C18S4 via LB deposition provides control over the J-aggregation process of TDBC-like molecules and can ultimately lead to tuning the J-aggregate coupling for specific experiments and applications.

Original languageEnglish
Pages (from-to)376-383
Number of pages8
JournalJournal of Luminescence
Volume158
DOIs
StatePublished - Feb 2015

Bibliographical note

Funding Information:
We gratefully acknowledge the professional support of Sivan Harazi and Dillon Schiff in putting the LB trough into a sealed glove-box and of David Rajsfus for the preliminary work on the synthesis. This research was financially supported by the ISF (Israel Science Foundation) , Grant number 206738 .

Publisher Copyright:
© 2014 Elsevier Inc. All rights reserved.

Keywords

  • Absorbance
  • Dye
  • J-aggregate
  • Langmuir-Blodgett
  • Monolayer
  • Photoluminescence

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