π-Extended Rubrenes via Dearomative Annulative π-Extension Reaction

Polycyclic Aromatic Hydrocarbon‐based Soft Materials: Applications in Fluorescent Detection, Gelation, AIEE and Mechanochromism

“…Likewise, challenging PAH‐derivatives such as tetracene, pentacene, pagoda[n]arenes, coronene, and rubrene also provide noteworthy future directions. In addition to novel structural features and notable properties, PAHs also offer many challenges [11,164–167] . For example, while synthesis of PAH‐derivatives involves multi‐step synthetic challenges; desirable functionalization poses different sets of challenges [165,168] .…”

“…In addition to novel structural features and notable properties, PAHs also offer many challenges. [11,[164][165][166][167] For example, while synthesis of PAH-derivatives involves multi-step synthetic challenges; desirable functionalization poses different sets of challenges. [165,168] At the same time, such challenges not only open newer synthetic avenues but also create opportunities for the development of next-generation PAH-materials with a myriad of properties and applications.…”

One-step synthesis of polycyclic thianthrenes from unfunctionalized aromatics by thia-APEX reactions

“…Previously, we have devoted our efforts toward the development of a one-step annulative π-extension (APEX) 13,14 reaction and a heteroatom-embedding APEX (hetero-APEX) 15 reaction for efficient and rapid access to large polycyclic aromatic hydrocarbons (PAHs), polycyclic heteroaromatics and nanographenes from readily available unfunctionalized aromatics. Recently, we also developed a sulfur-embedding APEX (thia-APEX) reaction for the one-step synthesis of π-extended thiopyrylium salts (Fig.…”

Skeletal Transformation of Unactivated Arenes Enabled by a Low-Temperature Dearomative (3 + 2) Cycloaddition

“…Beginning in 2016, the Sarlah group reported that the (4 + 2) photoadducts of simple arenes and 1,2,4-triazoline-3,5-diones (TADs), though thermally unstable above −10 °C in the case of monocyclic arenes, could be successfully intercepted at low temperatures with suitable reagents (Scheme a). Through dihydroxylations, reductions, catalytic allylic substitutions, hydroborations, epoxidations, and cyclopropanations, among others, the initial cycloadducts were elaborated to provide polysubstituted carbocycles . In 2021, the Brown and Glorius groups jointly reported that triplet photosensitization enabled the para -cycloaddition of alkenes with quinolines, isoquinolines, or quinazolines under acidic conditions (Scheme b) .…”