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TriQuinoline.
Shinya Adachi1, Masakatsu Shibasaki1, Naoya Kumagai2
1Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo, 141-0021, Japan.
Nature Communications
|August 25, 2019
Summary
We synthesized TriQuinoline (TQ), a molecular model for pyridinic-nitrogen defects in graphene. This novel molecule exhibits high proton affinity and acts as an efficient DNA intercalator, inhibiting topoisomerase I activity.
Area of Science:
- Materials Science
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Structurally defined graphitic materials are key to understanding their properties and functions.
- Pyridinic-nitrogen defects in graphene influence its electronic and chemical behavior.
Purpose of the Study:
- To design and synthesize TriQuinoline (TQ) as a molecular model for pyridinic-nitrogen defects.
- To investigate the physicochemical properties and supramolecular interactions of TQ.
Main Methods:
- Bottom-up synthesis of a quinoline trimer (TQ).
- Computational and empirical confirmation of proton affinity.
- Formation and characterization of a ternary complex involving TQ•H+, coronene, and [12]cycloparaphenylene.
Main Results:
- Successful synthesis of TQ with unusual aromatization behavior.
- TQ exhibits high proton affinity due to its central void.
- TQ•H+ forms a ternary complex with coronene and [12]cycloparaphenylene.
- TQ•H+ demonstrates water-miscibility and acts as a DNA intercalator.
Conclusions:
- TQ serves as an effective molecular model for pyridinic-nitrogen defects in graphene.
- The unique structure of TQ enables high proton affinity and complex formation.
- TQ•H+ shows potential as a DNA intercalator for biological applications, including topoisomerase I inhibition.