1. Umbrella‐Shaped Amphiphiles: Internal Alkylation of an Aromatic Micelle and Its Impact on Cavity Features.
- Author
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Endo, Masaya, Aoyama, Shinji, Tsuchido, Yoshitaka, Catti, Lorenzo, and Yoshizawa, Michito
- Subjects
AMPHIPHILES ,STRUCTURAL stability ,MICELLES ,ANTHRACENE ,EMISSIVITY - Abstract
To develop new hybrid micelles with alkyl/polyaromatic core–shell structures, we synthesized umbrella‐shaped amphiphiles bearing a bent anthracene dimer with a linear alkyl chain (i.e. octyl and hexadecyl groups). The amphiphiles quantitatively assemble into spherical micelles (~2–3 nm in core diameter), possessing an alkylated cavity surrounded by a polyaromatic framework, in water. The alkylation significantly enhances the stability of the micellar structures against dilution (up to 9 μM) and heat (up to >120 °C). The highly condensed hexadecyl core of the hybrid micelle, as indicated by solvatochromic guest probes, displays increased uptake ability toward large alkylated metallodyes. Interestingly, efficient uptake of aromatic macrocycles (i.e. [n]cycloparaphenylenes) by the present micelle provides pseudorotaxane‐shaped host–guest composites with high emissivity (ΦF=up to 35 %). Internal multi‐alkylation of an aromatic micelle can thus successfully enhance its assembly stability/guest uptake functions. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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