TriQuinoline

Shinya Adachi, Masakatsu Shibasaki and Naoya Kumagai ()
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Shinya Adachi: Institute of Microbial Chemistry
Masakatsu Shibasaki: Institute of Microbial Chemistry
Naoya Kumagai: Institute of Microbial Chemistry

Nature Communications, 2019, vol. 10, issue 1, 1-11

Abstract: Abstract The bottom-up synthesis of structurally well-defined motifs of graphitic materials is crucial to understanding their physicochemical properties and to elicit new functions. Herein, we report the design and synthesis of TriQuinoline (TQ) as a molecular model for pyridinic-nitrogen defects in graphene sheets. TQ is a trimer of quinoline units concatenated at the 2- and 8-positions in a head-to-tail fashion, whose structure leads to unusual aromatisation behaviour at the final stage of the synthesis. The central atomic-sized void endows TQ with high proton affinity, which was confirmed empirically and computationally. TQ•H+ is a two-dimensional cationic molecule that displays both π–π and CH–π contact modes, culminating in the formation of the ternary complex ([12]cycloparaphenylene(CPP) ⊃ (TQ•H+/coronene)) that consists of TQ•H+, coronene (flat), and [12]cycloparaphenylene ([12]CPP) (ring). The water-miscibility of TQ•H+ allows it to serve as an efficient DNA intercalator for e.g. the inhibition of topoisomerase I activity.

Date: 2019
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DOI: 10.1038/s41467-019-11818-1

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