Synthesis and characterization of membrane stable bis(arylimino)isoindole dyes and their potential application in nano-biotechnology

Benjamin Kim, Ceren Yalaz, Dipanjan Pan

Research output: Contribution to journalArticlepeer-review

Abstract

A synthetic methodology of preparing novel membrane stable, responsive dyes is revealed in this manuscript. 1,3-Bis(arylimino)isoindole dyes were synthesized and their properties to undergo intramolecular hydrogen bonding was studied with fluorescence spectroscopy in varying solvent polarities. Based on the functional moieties, compound that is capable of hydrogen donor and acceptor interactions produces predominant photoexcitation in comparison to the responsive dyes that lack these functionalities. These dyes, by the virtue of the presence of long chain acyl groups could be incorporated stably within the phospholipids membrane of core-shell nanoparticles. Nanoparticle was 'cracked' to release the dye from a hydrophobic to a hydrophilic environment. A significant change in florescence intensity was then observed, indicating the direct change in effect of intramolecular hydrogen bonding based on solvent polarity changes. This unique study provided implications of many further applications toward nanomedicine and nano-biotechnology.

Original languageEnglish (US)
Pages (from-to)4134-4137
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number32
DOIs
StatePublished - Aug 8 2012

Keywords

  • Bis(imino)isoindole
  • Fluorescence dye
  • Membrane stable
  • Nano-biotechnology
  • Responsive dyes

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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