Pyridinic Nanographenes by Novel Precursor Design. Issue 6 (12th January 2021)

• Record Type: Journal Article
• Authors: Reger, David; Schöll, Kilian; Hampel, Frank; Maid, Harald; Jux, Norbert
• Is Part Of: Chemistry. Volume 27:Issue 6(2021)
• Page Start: 1984
• Page End: 1989
• Publication Date: 2021-01-12
• Subjects: heterocycles -- nanographene -- polycyclic aromatic hydrocarbons -- pyridine -- Scholl oxidation; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202004983
• Languages: English
• ISSNs: 0947-6539

Abstract

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 π‐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. Abstract : An efficient Scholl oxidation to obtain pyridine HBCs is reported in this work. The concept is based on the pre‐formation of bonds at the otherwise unreactive 3/3' positions of the pyridine. Post‐functionalization at the nitrogen atom by alkylation, oxidation, and coordination is demonstrated together with photophysical and electrochemical characterization of the obtained products.