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A Polyaromatic Gemini Amphiphile That Assembles into a Well‐Defined Aromatic Micelle with Higher Stability and Host Functions
Author(s) -
Nishioka Tomoya,
Kuroda Kiyonori,
Akita Munetaka,
Yoshizawa Michito
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201814624
Subject(s) - amphiphile , micelle , chemistry , molecule , amphiphilic molecule , fluorescence , organic chemistry , polymer chemistry , chemical engineering , copolymer , aqueous solution , polymer , quantum mechanics , engineering , physics
A gemini‐type amphiphilic molecule, constituted of two V‐shaped polyaromatic amphiphiles linked by a linear acetylene spacer, was synthesized. The gemini amphiphile assembles into a well‐defined aromatic micelle (ca. 2 nm in core diameter), providing higher stability in water even at low concentration (0.09 m m ) and high temperature (>130 °C). Unlike common gemini amphiphiles with aliphatic chains, the present amphiphile and its micellar assembly emit green and orange fluorescence ( Φ F =33 and 9 %), respectively. Despite strong and multiple π‐stacks of the polyaromatic panels of the amphiphiles, the water‐soluble gemini aromatic micelle incorporates medium‐size to large hydrophobic compounds into the frameworks. Interestingly, the guest binding capability toward large planar molecules was enhanced by more than two times through the pre‐encapsulation of spherical molecules in the cavity.