In2Q2: A New Entry of 16‐Membered Tetraazamacrocycle Concatenating Indole and Quinoline Units

Author:

Kihara Kazuki1ORCID,Kobayashi Toi1ORCID,Xu Wei1ORCID,Kumagai Naoya12ORCID

Affiliation:

1. Graduate School of Pharmaceutical Sciences Keio University 1-5-30 Shibakoen, Minato-ku Tokyo 105-8512 Japan

2. Institute of Microbial Chemistry Tokyo 141-0021 Japan

Abstract

AbstractA new family of 16‐membered macrocycles comprising two indole (In) and two quinoline (Q) units, coined In2Q2, was synthesized. Each unit is diagonally located and concatenated in a head‐to‐tail fashion, furnishing a non‐flat saddle‐shaped architecture with C2 symmetry. The synthetic protocol utilizing macrocyclic diamide as a pivotal precursor allowed us to access a series of In2Q2 derivatives bearing various substituents on the periphery. The In2Q2 derivatives and their Zn2+ complexes were emissive in both solution phase and solid state. While the entire architecture of In2Q2 is similar to that of quinoline tetramer TEtraQuinoline, a couple of contrasting physicochemical properties were revealed.

Funder

Japan Society for the Promotion of Science

Publisher

Wiley

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