A water-soluble mechanochromic luminescent pyrene derivative exhibiting recovery of the initial photoluminescence color in a high-humidity environment

Yoshimitsu Sagara, Toru Komatsu, Tasuku Ueno, Kenjiro Hanaoka, Takashi Kato, Tetsuo Nagano

Research output: Contribution to journalArticlepeer-review

67 Citations (Scopus)

Abstract

Switching of the luminescence properties of molecular materials in response to mechanical stimulation is of fundamental interest and also has a range of potential applications. Herein, a water-soluble mechanochromic luminescent pyrene derivative having two hydrophilic dendrons is reported. This pyrene derivative is the first example of a mechanochromic luminescent organic compound that responds to relative humidity. Mechanical stimulation (grinding) of this pyrene derivative in the solid state results in a change of the photoluminescence from yellow to green. Subsequent exposure to water vapor induces recovery of the initial yellow photoluminescence. The color change is reversible through at least ten cycles. It is also demonstrated that this compound can be applied as a mechano-sensing material in frictional wear testing for grease, owing to its immiscibility in non-polar solvents and its non-crystalline behavior. Transmission electron microscope and atomic force microscope observations of samples prepared from dilute aqueous solutions of the pyrene derivative on suitable substrates, together with dynamic light scattering measurements for the compound in aqueous solution, indicate that this amphiphilic dumbbell-shaped molecule forms micelles in water.

Original languageEnglish
Pages (from-to)5277-5284
Number of pages8
JournalAdvanced Functional Materials
Volume23
Issue number42
DOIs
Publication statusPublished - 2013 Nov 13
Externally publishedYes

Keywords

  • mechanochromic luminescence
  • self-assembly
  • stimuli-responsive materials
  • supramolecular chemistry
  • thermochromic luminescence

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

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