棒状の芳香族分子を“ねじる” ーカプセル化によるキラル光学特性の発現ー

2026-10-15 東京科学大学

図1. a）棒状芳香族分子にキラル光学特性を付与する2つの方法。キラル側鎖の導入（左）とキラルカプセルの内包による棒状芳香族分子の光学活性化（右）、b）キラル両親媒性分子sBAMによるキラル分子カプセルsBCの形成。

＜関連情報＞

• https://www.isct.ac.jp/ja/news/75fd6kr2v1lg
• https://onlinelibrary.wiley.com/doi/10.1002/anie.4171725

軸不斉芳香族カプセル内における線状芳香族オリゴマーの非共有結合性PL、CD、およびCPL活性化 Non-Covalent PL, CD, and CPL Activation of Linear Aromatic Oligomers within Axially Chiral Aromatic Capsules

Yoshihisa Hashimoto, Yuya Tanaka, Daiki Tauchi, Masashi Hasegawa, Michito Yoshizawa
Angewandte Chemie International Edition  Published: 22 August 2026
DOI:https://doi.org/10.1002/anie.4171725

ABSTRACT

Covalent functionalization is requisite to enhancing/inducing the luminescent and chiroptical properties of oligo-aromatic compounds, owing to their rigid framework and strong aggregation characters. Here we report that linear aromatic oligomers display intense PL, CD, and CPL properties upon encapsulation by axially-chiral aromatic capsules under ambient aqueous conditions. The treatment of para-phenylene oligomers with chiral BINOL-based amphiphiles generates host-guest composites in water, exhibiting oligomer-based PL, CD, and CPL bands with strong intensities (up to Φ_F = 36%, |g_abs| = 6 × 10⁻³, and |g_lum| = 3 × 10⁻³). This method is applicable to other aromatic oligomers, comprising fluorene, carbazole, and thiophene rings, and further PL and CPL enhancement (up to Φ_F = 87% and |g_lum| = 4 × 10⁻³) is demonstrated with the resultant composites. The observed chiroptical features stem from tight host-guest CH-π interactions in the adaptable aromatic cavity. Besides the oligomers, polymer-based chiroptical activities are found from the corresponding polymers upon encapsulation. In the solid state, the host-guest composites display further prominent CD and CPL bands, using fluorene trimers (|g_abs| = |g_lum| = ∼3 × 10⁻²). This study is the first example of the PL, CD, and CPL activation of simple aromatic oligomers to a large extent, via non-covalent encapsulation. The present strategy will facilitate the supramolecular fusion between aromatic oligo/polymers and chiral functions.