π-extended pyrenes: from an antiaromatic buckybowl to doubly curved nanocarbons with gulf architectures.

ABSTRACT: The synthesis of π-extended pyrenes keeps attracting considerable attention. In particular, frameworks containing nonbenzenoid rings might display intriguing properties. Here, we report a practical synthetic pathway to access a new buckybowl (1), which is composed of four five-membered rings externally fused to a pyrene core. The buckybowl 1 exhibits antiaromaticity involving 22 π-electrons, a rapid bowl-to-bowl interconversion, and a small band gap. Furthermore, this buckybowl could be subjected to Scholl cyclodehydrogenation to prepare the doubly curved nanocarbons (2_rac and 2_meso), which exist as two diastereomers, as demonstrated by X-ray crystal structure determination. Variable temperature ¹H NMR measurements reveal that 2_meso can isomerize

SUBMITTER: Liu B 

PROVIDER: S-EPMC11421037 | biostudies-literature | 2024 Sep

REPOSITORIES: biostudies-literature