Facile synthesis of an ambient stable pyreno[4,5-b]pyrrole monoanion and pyreno[4,5-b:9,10-b']dipyrrole dianion: from serendipity to design.

ABSTRACT: The stability of singly or multiply negatively charged π-conjugated organic compounds is greatly influenced by their electronic delocalization. Herein, we report a strategic methodology for isolation of a mysterious compound. The isolated compounds, a pyreno[4,5-b]pyrrole monoanion and pyreno[4,5-b:9,10-b']dipyrrole dianion, were highly stable under ambient conditions due to high delocalization of the negative charge over multiple electron deficient C[triple bond, length as m-dash]N groups and pyrene π-scaffolds and allowed purification by column chromatography. To our knowledge, this is the first report on TCNE type reductive condensation of malononitrile involving pyrene di- and tetraone and formation of pyrenopyrrole. All compounds were characterized by spectroscopi

SUBMITTER: Kumar S 

PROVIDER: S-EPMC8826763 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature