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Pyridinic Nanographenes by Novel Precursor Design.

ABSTRACT: In this work we present the solution-synthesis of pyridine analogues to hexa-peri-hexabenzocoronene (HBC)-which might be called superpyridines-via a novel precursor design. The key step in our strategy was the pre-formation of the C-C bonds between the 3/3' positions of the pyridine and the adjacent phenyl rings-bonds that are otherwise unreactive and difficult to close under Scholl-conditions. Apart from the synthesis of the parent compound we show that classical pyridine chemistry, namely oxidation, N-alkylation and metal-coordination is applicable to the ?-extended analogue. Furthermore, we present basic physical chemical characterizations of the newly synthesized molecules. With this novel synthetic strategy, we hope to unlock the pyridine chemistry of nanographenes.

SUBMITTER: Reger D

PROVIDER: S-EPMC7898602 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Pyridinic Nanographenes by Novel Precursor Design.

Reger David D Schöll Kilian K Hampel Frank F Maid Harald H Jux Norbert N

Chemistry (Weinheim an der Bergstrasse, Germany) 20210112 6

In this work we present the solution-synthesis of pyridine analogues to hexa-peri-hexabenzocoronene (HBC)-which might be called superpyridines-via a novel precursor design. The key step in our strategy was the pre-formation of the C-C bonds between the 3/3' positions of the pyridine and the adjacent phenyl rings-bonds that are otherwise unreactive and difficult to close under Scholl-conditions. Apart from the synthesis of the parent compound we show that classical pyridine chemistry, namely oxid ...[more]

PMID: 33225488

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