Synthesis and Design of Aggregation-Induced Emission Surfactants: Direct Observation of Micelle Transitions and Microemulsion Droplets.

The direct visualization of micelle transitions is a long-standing challenge owing to the intractable aggregation-caused quenching of light emission in the micelle solution. Herein, we report the synthesis of a surfactant with a tetraphenylethene (TPE) core and aggregation-induced emission (AIE) characteristics. The transition processes of surfactant micelles and the microemulsion droplets (MEDs) formed by the surfactant with a TPE core were clearly visualized by a high-contrast fluorescence imaging method. The fluorescence intensity of the MEDs decreased as the size of MEDs increased as a result of weakening of the restriction of intramolecular rotation (RIR). The results of this study deepen our understanding of micelle-transition processes and provide solid evidence in favor of the hypothesis that the AIE phenomenon has its origin in the RIR of fluorophores in the aggregate state.

[1]  R. Griffin,et al.  Phenyl ring dynamics in a tetraphenylethylene-bridged metal-organic framework: implications for the mechanism of aggregation-induced emission. , 2012, Journal of the American Chemical Society.

[2]  J. J. López-García,et al.  Poisson-Boltzmann description of the electrical double layer including ion size effects. , 2011, Langmuir : the ACS journal of surfaces and colloids.

[3]  M. Yoshizawa,et al.  Polyaromatic nanocapsules displaying aggregation-induced enhanced emissions in water. , 2015, Journal of the American Chemical Society.

[4]  S. Ezrahi,et al.  Properties, main applications and perspectives of worm micelles. , 2006, Advances in colloid and interface science.

[5]  D. Vezenov,et al.  A double-tailed fluorescent surfactant with a hexavanadate cluster as the head group. , 2011, Angewandte Chemie.

[6]  J. S. Pedersen,et al.  Monitoring the transition from spherical to polymer-like surfactant micelles using small-angle X-ray scattering. , 2014, Angewandte Chemie.

[7]  B. Song,et al.  Water-soluble nano-fluorogens fabricated by self-assembly of bolaamphiphiles bearing AIE moieties: towards application in cell imaging. , 2015, Journal of materials chemistry. B.

[8]  A. Rananaware,et al.  Tetraphenylethene-based star shaped porphyrins: synthesis, self-assembly, and optical and photophysical study. , 2015, The Journal of organic chemistry.

[9]  D. Musaev,et al.  [12]Annulene gemini surfactants: structure and self-assembly. , 2007, Angewandte Chemie.

[10]  Hsiung-Lin Tu,et al.  Nonionic fluorescent oligomeric surfactant for ordered mesoporous silica structure , 2006 .

[11]  D. Grahame.  The electrical double layer and the theory of electrocapillarity. , 1947, Chemical reviews.

[12]  Ben Zhong Tang,et al.  Protein detection and quantitation by tetraphenylethene-based fluorescent probes with aggregation-induced emission characteristics. , 2007, The journal of physical chemistry. B.

[13]  Ben Zhong Tang,et al.  Aggregation-induced emission. , 2011, Chemical Society reviews.

[14]  M. J. Rosen,et al.  Surfactants and Interfacial Phenomena: Rosen/Surfactants 4E , 2012 .

[15]  S. P. Moulik,et al.  Interfacial composition and thermodynamics of formation of water/isopropyl myristate water-in-oil microemulsions stabilized by butan-1-ol and surfactants like cetyl pyridinium chloride, cetyl trimethyl ammonium bromide, and sodium dodecyl sulfate , 2002 .

[16]  H. Hoffmann,et al.  Surfactants, Micelles and Fascinating Phenomena , 1988 .

[17]  M. Dincǎ,et al.  Turn-on fluorescence in tetraphenylethylene-based metal-organic frameworks: an alternative to aggregation-induced emission. , 2011, Journal of the American Chemical Society.

[18]  Fang Zeng,et al.  Hyperbranched polyester-based fluorescent probe for histone deacetylase via aggregation-induced emission. , 2013, Biomacromolecules.

[19]  J. S. Pedersen,et al.  Direct observation of the formation of surfactant micelles under nonisothermal conditions by synchrotron SAXS. , 2013, Journal of the American Chemical Society.

[20]  H S Kwok,et al.  Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. , 2001, Chemical communications.

[21]  Ben Zhong Tang,et al.  Aggregation‐Induced Emission: The Whole Is More Brilliant than the Parts , 2014, Advanced materials.

[22]  K. Chou,et al.  Re-evaluating the surface tension analysis of polyelectrolyte-surfactant mixtures using phase-sensitive sum frequency generation spectroscopy. , 2014, Journal of the American Chemical Society.

[23]  Jinhe Kim,et al.  Polarity Effect of Exterior Chains on Self-Assembled Structure and Aggregation Mechanism of Tetraphenylethene Derivatives in THF/Water Mixtures , 2015 .

[24]  D. Ding,et al.  Bioprobes based on AIE fluorogens. , 2013, Accounts of chemical research.

[25]  S. Saha,et al.  The Schulman Method of Cosurfactant Titration of the Oil/Water Interface (Dilution Method): A Review on a Well-Known Powerful Technique in Interfacial Science for Characterization of Water-in-Oil Microemulsions , 2015 .

[26]  H. Hoffmann,et al.  Tenside, Micellen und faszinierende Phänomene , 1988 .

[27]  S. Raghavan,et al.  Microstructural Changes in SDS Micelles Induced by Hydrotropic Salt , 2002 .

[28]  Jian Wang,et al.  Click synthesis, aggregation-induced emission, E/Z isomerization, self-organization, and multiple chromisms of pure stereoisomers of a tetraphenylethene-cored luminogen. , 2012, Journal of the American Chemical Society.

[29]  B. Tang,et al.  AIE macromolecules: syntheses, structures and functionalities. , 2014, Chemical Society reviews.

[30]  Xiaohu Gao,et al.  An aggregation-induced-emission platform for direct visualization of interfacial dynamic self-assembly. , 2014, Angewandte Chemie.

[31]  Elodie Soussan,et al.  Wirkstofftransport mit weicher Materie: Matrix- und Vesikelvektoren , 2009 .

[32]  Elodie Soussan,et al.  Drug delivery by soft matter: matrix and vesicular carriers. , 2009, Angewandte Chemie.

[33]  Dong Yang,et al.  Anion-coordination-induced turn-on fluorescence of an oligourea-functionalized tetraphenylethene in a wide concentration range. , 2014, Angewandte Chemie.

[34]  Hong-Xia Wang,et al.  Rheological Properties and Microstructures of Anionic Micellar Solutions in the Presence of Different Inorganic Salts , 2002 .

[35]  Sebastian Reineke,et al.  Selective turn-on ammonia sensing enabled by high-temperature fluorescence in metal-organic frameworks with open metal sites. , 2013, Journal of the American Chemical Society.