Designing lower critical solution temperature behavior into a discotic small molecule

Gary J. Richards, Jan Labuta, Jonathan P. Hill, Toshiyuki Mori, Katsuhiko Ariga

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)


Design and analysis of amphiphilic small molecules exhibiting lower critical solution temperature (LCST) behavior is reported. 2,3,6,7,10,11- Hexakis[2-(N,N-dialkylamino)ethoxy] triphenylenes containing hydrophilic groups attached at their discotic core were prepared, and the LCST behavior of their solutions was studied using fluorescence spectrophotometry and 1H NMR spectroscopy. 1H NMR spin-lattice relaxation times were used to assess the rotational mobility of molecules below and above the clouding point. The impact on the LCST of supramolecular π-π stacking forces introduced by the triphenylene (TP) core was studied. The operation of the LCST phenomenon was found not to depend significantly on stacking of TP moieties. This process in small molecular species offers several advantages over the polymer-originated phenomenon. For instance, enabling an analogue of the LCST transition in dye molecules might allow the design of novel optical devices by permitting previously unavailable specific aggregated states.

Original languageEnglish
Pages (from-to)1336-1340
Number of pages5
JournalJournal of Physical Chemistry Letters
Issue number9
Publication statusPublished - 2010 May 6
Externally publishedYes


  • Macromolecules
  • Soft Matter

ASJC Scopus subject areas

  • Materials Science(all)
  • Physical and Theoretical Chemistry


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