2020
DOI: 10.1002/chem.201905794
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Boron–Nitrogen‐Doped Nanographenes: A Synthetic Tale from Borazine Precursors

Abstract: In this work, ac omprehensive account of the authors' synthetic efforts to prepareb orazino-doped hexabenzocoronenes by using the Friedel-Crafts-type electrophilic aromatic substitution is reported. Hexafluoro-functionalized aryl borazines, bearing an ortho fluoride leaving group on each of the N-and B-aryl rings,w as shown to lead to cascade-type electrophilica romatic substitution events in the stepwise CÀCbond formation, giving higher yields of borazinocoronenes than those obtained with borazine precursors … Show more

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Cited by 28 publications
(19 citation statements)
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“…Among the available methods for synthesizing 1,2‐azaborine containing PAHs, the electrophilic borylation, introduced by Dewar [2a] and optimized further, is attractive as both B−N and B−C bonds are constructed in one synthetic step (Scheme 1 a). [2h, 3a, 4] Alternatively, the coupling of carbon‐carbon (CC) bonds around existing BN units has occasionally been employed, e.g., by Piers, [5] Bonifazi, [3b, 6] and our group (Scheme 1 b). [7] The Wagner group [8] described the Au catalyzed NC bond formation as the final step of the synthesis of a doubly BN substituted perylene (Scheme 1 c).…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…Among the available methods for synthesizing 1,2‐azaborine containing PAHs, the electrophilic borylation, introduced by Dewar [2a] and optimized further, is attractive as both B−N and B−C bonds are constructed in one synthetic step (Scheme 1 a). [2h, 3a, 4] Alternatively, the coupling of carbon‐carbon (CC) bonds around existing BN units has occasionally been employed, e.g., by Piers, [5] Bonifazi, [3b, 6] and our group (Scheme 1 b). [7] The Wagner group [8] described the Au catalyzed NC bond formation as the final step of the synthesis of a doubly BN substituted perylene (Scheme 1 c).…”
Section: Methodsmentioning
confidence: 99%
“…Perylenes and dibenzoperylenes with BN doping have been synthesized by Wagner, Bonifazi and our group [3b, 4j, 8, 10] . We have developed a multistep synthesis of a dibenzoperylene 1 that features a BNBN unit at its bay region [4j] .…”
Section: Methodsmentioning
confidence: 99%
“…The insoluble unsubstituted 19.9 , previously reported in an on-surface synthesis (CR2017, section 2.3.2 ), was also obtained via the same silane-based protocol. 35 …”
Section: Coronenoidsmentioning
confidence: 99%
“…Coronene nanocrystals have been used in the creation of graphene (Kato et al, 2021;Saha and Bhattacharyya, 2018). The properties of pure coronene and its boron nitride substitution were considered (Dosso et al, 2020;Kurita, 2000;Vessally et al, 2017). Lithium as a dopant has already been reported to reduce the stability of coronene more than three times (Forozmand and Biglari, 2021).…”
Section: Introductionmentioning
confidence: 99%