Fully fused boron-doped polycyclic aromatic hydrocarbons: their synthesis, structure–property relationships, and self-assembly behavior in aqueous media

Abstract

Planarized triarylboranes are attracting increasing attention not only as models of boron-doped graphenes, but also as promising materials for organic optoelectronics. In particular, polycyclic aromatic hydrocarbon (PAH) skeletons with embedded...

Planarized Phenyldithienylboranes: Effects of the Bridging Moieties and π‐Extension on the Photophysical Properties and Lewis Acidity

“…Although the degree of variation is relatively small, these results demonstrate that the Lewis acidity of the boron center can be turned by the electronic effects of the substituents located at a position that is remote from the boron center. We have already demonstrated that the weak Lewis acid–base complexation with pyridine can be the key to bestow boron‐doped π‐electron systems with various functions, such as chemisorption, [5b] dual fluorescence properties, [6a,9b] thin‐film processability, [6b] and afford control over supramolecular polymerization processes [15b–d] . Therefore, the present results may provide further useful guidelines for the fine‐tuning of the functions of such planarized triarylboranes.…”

Double boron-embedded multiresonant thermally activated delayed fluorescent materials for organic light-emitting diodes

“…There are two types mainly utilized for the synthesis of the DB-MR-TADF emitters. These are (i) BuLi-based tandem borylation using Hunig base; (ii) One shot double borylation by using BBr 3 / BI 3 and reducing aromatic solvents 49,[83][84][85][86][87][88][89][90] . In type-1, under the inert atmosphere in the reducing solvents, the halogen will be replaced by using lithiation, and then transmetalation was done by using BBr 3 with the temperature controls [90][91][92][93] .…”

“…These are (i) BuLi -based tandem borylation using Hunig base; (ii) One shot double borylation by using BBr 3 /BI 3 and reducing aromatic solvents 49 , 83 – 90 . In type-1, under the inert atmosphere in the reducing solvents, the halogen will be replaced by using lithiation, and then transmetalation was done by using BBr 3 with the temperature controls 90 – 93 . And then finally, the tandem bora Friedel-craft reactions using the Hunig base.…”

Fully-fused boron-doped olympicenes: modular synthesis, tunable optoelectronic properties, and one-electron reduction

“…For instance, by introducing well-tailored structural constraints, Yamaguchi and co-workers have reported a series of B-doped PAHs with boron atoms embedded at the non-edge position of their fully-conjugated skeletons by dehydrogenative aromatic C–C coupling reactions. 7 Although lacking bulky protecting groups, these PAHs not only exhibited much-improved chemical stability against oxygen and moisture but also showed substantial π-stacking capability and robust Lewis acidity to form intriguing Lewis acid–base adducts. Wagner, 8 Hatakeyama, 9 and Ingleson 10 also developed diverse fully-fused B-doped PAHs based on different sophisticated synthetic strategies.…”

“…In addition, the inherent electron-deficient nature of incorporated boron atoms might further endow these boraolympicenyl derivatives with extra fascinating electronic properties/functions like electron-accepting and/or transporting characteristics, high Lewis acidity to form labile adducts with charge-neutral Lewis bases, and so on. 7–10 However, as mentioned above, due to the lack of efficient synthetic methodologies, to the best of our knowledge, to date the preparation of such boraolympicenyl derivatives with fully-fused boron atoms is still remaining unexplored, not to speak of the illustration and modulation of boron-substitution effect on the physicochemical and molecular packing properties of these novel graphenoid PAHs.…”