Overview

TriQuinoline, or TQ, was designed as an atom-size-deficient pseudo-planar trimer of quinoline. The small central cavity gives the molecule strong proton-binding ability, while the aromatic surface allows it to interact with other π-systems through face-to-face and edge-to-face contacts.

That combination is unusual. TQ looks like a lipophilic aromatic molecule, but it can behave in ways that are closer to a compact supramolecular host. It forms complexes with aromatic guests, intercalates into DNA, and points toward applications in biological activity, liquid-liquid phase separation, and removal of polycyclic aromatic hydrocarbons.

More recently, we have been expanding the family: adding heteroatoms, changing ring number, and moving from flat systems toward more three-dimensional architectures. The goal is to make molecules that are not just beautiful on a slide, but also useful as hosts, binders, and catalytic platforms.

What we are asking

Visual Notes

Representative Publications

1. TriQuinoline
   S. Adachi, M. Shibasaki, N. Kumagai
   Nature Commun. 2019, 10, 3820.
2. TEtraQuinolines: A Missing Link in the Family of Porphyrinoid Macrocycles
   Wei Xu, Yuuya Nagata, and Naoya Kumagai*
   J. Am. Chem. Soc. 2023, 145, 2609-2618.
3. Oxa-TriQuinoline: A New Entry to Aza-Oxa-Crown Architectures
   Toi Kobayashi and Naoya Kumagai*
   Angew. Chem. Int. Ed. 2023, 62, e202307896.
4. TriQuinazoline and Related Quinoline/Quinazoline Cyclic Trimers: Unified Synthesis, Planar Discotic Architecture, and Proton Dynamics in an Atomic-Scale Cavity
   Takuya Sakurai, Ryosuke Tsutsumi, and Naoya Kumagai*
   Chem. Mater. 2026, 38, 2453-2463.

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