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

doi:10.1021/cm400988a

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 journal › Article › peer-review

59 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 language	English
Pages (from-to)	3288-3295
Number of pages	8
Journal	Chemistry of Materials
Volume	25
Issue number	16
DOIs	https://doi.org/10.1021/cm400988a
Publication status	Published - 2013 Aug 27

Keywords

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

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
Materials Chemistry

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10.1021/cm400988a

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title = "Water-soluble fluorinated and PEGylated cyanostilbene derivative: An amphiphilic building block forming self-assembled organic nanorods with enhanced fluorescence emission",

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.",

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AU - Kim, Sehoon

AU - Park, Soo Young

PY - 2013/8/27

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N2 - 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.

AB - 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.

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Water-soluble fluorinated and PEGylated cyanostilbene derivative: An amphiphilic building block forming self-assembled organic nanorods with enhanced fluorescence emission

Abstract

Keywords

ASJC Scopus subject areas

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