Water-soluble fluorinated and PEGylated cyanostilbene derivative

An amphiphilic building block forming self-assembled organic nanorods with enhanced fluorescence emission

Seunghoon Shin, Se Hoon Gihm, Chong Rae Park, Sehoon Kim, Soo Young Park

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

We report synthesis and optical/structural characterization of new fluorescent rod-coil amphiphiles based on the PEGylated α-cyanostilbene skeleton (12EO-CNMBE and 12EO-CNTFMBE) and their self-assembly behaviors in water. Distinct from the common amphiphilic behavior of nonfluorinated 12EO-CNMBE forming spherical nanostructures, fluorinated 12EO-CNTFMBE has proven to be the first example of a molecular building block that can self-assemble in water into small-dimension, small-aspect-ratio organic nanorods with aggregation-induced enhanced emission (AIEE). The robust structural integrity and hydrophobic/π-conjugated nature of the fluorinated block assembly, as well as the antifouling coating by the hydrophilic PEG block, enabled stable encapsulation of a model drug (Nile Red) within the self-assembled nanorod structure and its successful delivery through membrane filters. By virtue of these advantageous attributes along with high intracellular uptake efficiency, the 12EO-CNTFMBE nanorods manifested potential as a self-signaling fluorescent nanocarrier for the intracellular delivery of hydrophobic cargos.

Original languageEnglish
Pages (from-to)3288-3295
Number of pages8
JournalChemistry of Materials
Volume25
Issue number16
DOIs
Publication statusPublished - 2013 Aug 27
Externally publishedYes

Fingerprint

Nanorods
Fluorescence
Derivatives
Water
Amphiphiles
Structural integrity
Encapsulation
Self assembly
Polyethylene glycols
Aspect ratio
Nanostructures
Agglomeration
Membranes
Coatings
Pharmaceutical Preparations

Keywords

  • aggregation-induced enhanced emission
  • bioimaging
  • cellular delivery carrier
  • fluorinated/PEGylated amphiphile
  • organic nanorods
  • self-assembly

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

Cite this

Water-soluble fluorinated and PEGylated cyanostilbene derivative : An amphiphilic building block forming self-assembled organic nanorods with enhanced fluorescence emission. / Shin, Seunghoon; Gihm, Se Hoon; Park, Chong Rae; Kim, Sehoon; Park, Soo Young.

In: Chemistry of Materials, Vol. 25, No. 16, 27.08.2013, p. 3288-3295.

Research output: Contribution to journalArticle

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