Photochemical and Direct
            <scp>CH</scp>
            Arylation Routes toward Carbon Nanomaterials

Morin, Jean‐François; Daigle, Maxime; Desroches, Maude

doi:10.1002/9783527695959.ch7

Cited by 5 publications

(7 citation statements)

References 73 publications

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“…The CDHC has experienced a true renaissance in recent years due to the work of Morin , who defined CDHC regioselectivity as follows: “ It is regioselective, meaning that new well‐defined architectures that were not accessible with the Scholl reaction could potentially be prepared .” [36, 38–40] However, solubility problems already emerged here as well [49] . In the last part of this work, we wanted to show that our new photo‐mechanochemical approach can be used to synthesize nanographenes regioselectively.…”

Section: Resultsmentioning

confidence: 99%

The Regioselective Solid‐State Photo‐Mechanochemical Synthesis of Nanographenes with UV light

et al. 2023

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Photochemical reactors inherently suffer from the low penetration depth of light and therefore rely on high dilutions to enable chemical reactions. Here we present the first method of UV (ultraviolet) photochemistry in the complete absence of bulk solvents in a ball mill. Triphenylene was synthesized by two routes, the Mallory reaction and the cyclodehydrochlorination (CDHC), resulting in yields of 81 and 92 %, respectively. The reaction was successfully scaled up to the gram scale and the robustness of the method was demonstrated for several different substrates. Finally, the regioselective assembly of nanographenes by mechanochemistry was demonstrated for larger systems. Thus, the mechanochemical approach presented here provides a powerful new tool for the atomically precise construction of nanographenes.

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Section: Resultsmentioning

confidence: 99%

The Regioselective Solid‐State Photo‐Mechanochemical Synthesis of Nanographenes with UV light

et al. 2023

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“…Die CDHC hat in den letzten Jahren eine wahre Renaissance erlebt, was auf die Arbeiten von Morin zurückzuführen ist, der die Regioselektivität der CDHC wie folgt definierte: “Sie ist regioselektiv, was bedeutet, dass neue, wohldefinierte Architekturen, die mit der Scholl‐Reaktion nicht zugänglich waren, potenziell hergestellt werden könnten .” [36, 38–40] Allerdings traten auch hier bereits Löslichkeitsprobleme auf [49] . Im letzten Teil dieser Arbeit wollten wir zeigen, dass unser neuer photo‐mechanochemischer Ansatz zur regioselektiven Synthese von Nanographenen verwendet werden kann.…”

Section: Ergebnisse Und Diskussionunclassified

“…[36,[38][39][40] Allerdings traten auch hier bereits Löslichkeitsprobleme auf. [49] Im letzten Teil dieser Arbeit wollten wir zeigen, dass unser neuer photo-mechanochemischer Ansatz zur regioselektiven Synthese von Nanographenen verwendet werden kann. Zu diesem Zweck haben wir die Substrate 1 g und 1 h verwendet.…”

Section: Ergebnisse Und Diskussionunclassified

UV‐Licht trifft Mechanochemie: Die Regioselektive Photochemische Festkörpersynthese von Nanographenen

et al. 2023

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Aufgrund der geringen Eindringtiefe von Licht sind photochemische Reaktoren auf hohe Verdünnungen angewiesen, um chemische Reaktionen zu ermöglichen. In diesem Beitrag stellen wir eine neue Methode der UV‐Photochemie in Abwesenheit großer Mengen Lösungsmitteln in einer Kugelmühle vor. Triphenylen wurde mittels der Mallory‐Reaktion und der Cyclodehydrochlorierung (CDHC) in Ausbeuten von 81 bzw. 92 % synthetisiert. Die CDHC wurde erfolgreich in den Gramm‐Maßstab skaliert, und die Robustheit der Methode für verschiedene Substrate nachgewiesen. Schließlich wurde der regioselektive Aufbau von Nanographenen für größere Systeme demonstriert. Der hier vorgestellte mechanochemische Ansatz bietet somit ein vielversprechendes neues Werkzeug zur Konstruktion von Nanographenen.

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“…congested aromatics [11][12][13][14]. Some of these limitations can be overcome by using prefunctionalized precursors [11], as exemplified by reductive Ullmann-type chemistry [15], catalytic direct arylations [11,14,16,17], photoinduced cyclodehydrochlorinations [18,19], or nucleophilic oxidative couplings [20], which may offer milder reaction conditions and superior regioselectivities, at the expense of atom and step economy [21]. The latter disadvantage may be obviated by transitionmetal-mediated double C-H bond activation [22,23], which is functionally equivalent to conventional oxidative coupling reactions, and has become a powerful synthetic tool with a rapidly growing scope of use [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Bipyrrole boomerangs via Pd-mediated tandem cyclization–oxygenation. Controlling reaction selectivity and electronic properties

Moshniaha¹,

Żyła‐Karwowska²,

Cybińska³

et al. 2020

Beilstein J. Org. Chem.

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Boomerang-shaped bipyrroles containing donor–acceptor units were obtained through a tandem palladium-mediated reaction consisting of a cyclization step, involving double C–H bond activation, and a double α-oxygenation. The latter reaction can be partly suppressed for the least reactive systems, providing access to α-unsubstituted boomerangs for the first time. These “α-free” systems are highly efficient fluorophores, with emission quantum yields exceeding 80% in toluene. Preliminary measurements show that helicene-like boomerangs may be usable as circularly polarized luminescent materials.

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Photochemical and Direct CH Arylation Routes toward Carbon Nanomaterials

Cited by 5 publications

References 73 publications

The Regioselective Solid‐State Photo‐Mechanochemical Synthesis of Nanographenes with UV light

The Regioselective Solid‐State Photo‐Mechanochemical Synthesis of Nanographenes with UV light

UV‐Licht trifft Mechanochemie: Die Regioselektive Photochemische Festkörpersynthese von Nanographenen

Bipyrrole boomerangs via Pd-mediated tandem cyclization–oxygenation. Controlling reaction selectivity and electronic properties

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