Organic diradicaloids have unique open-shell structures and properties and promising applications in organic electronics and spintronics. Incorporation of heteroatoms is an effective strategy to alter the electronic structures of organic diradicaloids. However, B-containing organic diradicaloids are very challenging due to their high reactivities, which are caused by not only diradical nature but also the B atom. In this article, we report a new kind of organic diradicaloids containing boron atoms. Our strategy is to incorporate planarized triarylboranes to antiaromatic polycyclic hydrocarbons (PHs). We synthesized two isomeric B-containing PHs composed of indenofluorene π-skeletons and two dioxa-bridged triphenylborane moieties. As proved by theoretical and experimental results, both of them have excellent ambient stability and open-shell singlet diradical structures, as well as intriguing magnetic and optoelectronic properties, such as thermally accessible triplet species, reversible multiredox ability, and narrow energy gaps. Notably, they possess sufficient Lewis acidity, which has never been observed for organic diradicaloids. In addition, they can coordinate with Lewis bases to form Lewis adducts, achieving unprecedented dynamic modulations of (anti)aromaticity and thus diradical character of organic diradicaloids.