Chiroptically Active Host–Guest Composites Using a Terpene-Based Micellar Capsule

For the design of a new chiroptically active host–guest system, a bent amphiphilic compound was synthesized using cyclic monoterpenes as key biorelated chiral frameworks. In water, the bent amphiphiles form a terpene-based micellar capsule with a core diameter of ∼2 nm in a spontaneous and quantitat...

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Published inJournal of the American Chemical Society Vol. 146; no. 34; pp. 23669 - 23673
Main Authors Hashimoto, Yoshihisa, Tanaka, Yuya, Suzuki, Daiya, Imai, Yoshitane, Yoshizawa, Michito
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 28.08.2024
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Summary:For the design of a new chiroptically active host–guest system, a bent amphiphilic compound was synthesized using cyclic monoterpenes as key biorelated chiral frameworks. In water, the bent amphiphiles form a terpene-based micellar capsule with a core diameter of ∼2 nm in a spontaneous and quantitative fashion. The resultant chiral capsule shows wide-ranging uptake abilities toward achiral fluorescent dyes in water. Notably, relatively strong CD bands are generated from the resultant host–guest composites, e.g., possessing AIE-active tetraphenylethene and sterically demanding BODIPY dyes, through efficient host-to-guest chirality transfer. The composites also display CPL, with moderate to high emission asymmetry factors (|g lum| = up to 3.3 × 10–3).
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content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.4c07193