Cleavage of non-polar C(sp²)‒C(sp²) bonds in cycloparaphenylenes via electric field-catalyzed electrophilic aromatic substitution.

ABSTRACT: Electrophilic aromatic substitution (EAS) is one of the most fundamental reactions in organic chemistry. Using an oriented external electric field (OEEF) instead of traditional reagents to tune the EAS reactivity can offer an environmentally friendly method to synthesize aromatic compounds and hold the promise of broadening its scope. Despite these advantages, OEEF catalysis of EAS is difficult to realize, due to the challenge of microscopically orienting OEEF along the direction of electron reorganizations. In this work, we demonstrate OEEF-catalyzed EAS reactions in a series of cycloparaphenylenes (CPPs) using the scanning tunneling microscope break junction (STM-BJ) technique. Crucially, the unique radial π-conjugation of CPPs enables a desired alignment for the OEEF to catalyze the EAS

SUBMITTER: Lin J 

PROVIDER: S-EPMC9849230 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature