Doubling the Length of the Longest Pyrene‐Pyrazinoquinoxaline Molecular Nanoribbons

Hernández-Culebras, Félix; Melle‐Franco, Manuel; Mateo‐Alonso, Aurelio

doi:10.1002/ange.202205018

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Angewandte Chemie

2022

DOI: 10.1002/ange.202205018

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Doubling the Length of the Longest Pyrene‐Pyrazinoquinoxaline Molecular Nanoribbons

Félix Hernández-Culebras

Manuel Melle‐Franco

Aurelio Mateo‐Alonso

Abstract: Molecular nanoribbons are a class of atomically‐precise nanomaterials for a broad range of applications. An iterative approach that allows doubling the length of the longest pyrene‐pyrazinoquinoxaline molecular nanoribbons is described. The largest nanoribbon obtained through this approach—with a 60 linearly‐fused ring backbone (14.9 nm) and a 324‐atoms core (C276N48)—shows an extremely high molar absorptivity (values up to 1 198 074 M−1 cm−1) that also endows it with a high molar fluorescence brightness (8700… Show more

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Cited by 10 publications

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Ribbon‐Type Boron‐Doped Polycyclic Aromatic Hydrocarbons: Conformations, Dynamic Complexation and Electronic Properties

et al. 2022

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Molecular ribbons (MRs), one-dimentional topological polycyclic aromatic hydrocarbons (PAHs), are of importance for synthetic chemistry and material sciences. Herein, we disclose an effective strategy to develop boron-doped MRs, i.e. photochemical cyclization on conjugated organoboranes for rapid π-extension. A series of ribbon-type boron-doped PAHs that own multiple cove edges were synthesized using Mallory photoreaction in solution. Two of them feature isomeric C 68 B 2 π-skeletons with 2.2 nm in length, thus representing a new kind of boron-doped MRs. The boron atoms endow them with sufficient Lewis acidity, and notably, the formed Lewis acid-base adducts based on borondoped MRs display the photo-induced dual-dissociation behavior in the excited state and thus photochromism property. Moreover, despite of the highly contorted topological conformations, their potential utility as organic semiconductor was demonstrated by fabrication of organic field-effect transistors.

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Ribbon‐Type Boron‐Doped Polycyclic Aromatic Hydrocarbons: Conformations, Dynamic Complexation and Electronic Properties

et al. 2022

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Bottom‐Up Preparation of Twisted Graphene Nanoribbons by Cu‐Catalyzed Deoxygenative Coupling

Gao

Hua

et al. 2022

Angewandte Chemie

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Graphene nanoribbons (GNRs) are promising in organic optoelectronic materials, and their properties largely depend on the size, edge, and conformation. Herein, the fully armchair-edged GNRs (AGNRs) with lengths up to 2.65 nm by using a Cu-catalyzed deoxygenative coupling as a key step. The resulting AGNRs (2HBT, 3HBT, and 4HBT) possess highly twisted πscaffolds, and the torsion angles between the adjacent triphenylene moieties are larger than 32°, as proved by crystallographic analyses. Theoretical and spectroscopic studies show that the butoxy groups endow AGNRs with electron-rich features, the extension of the π-system from 2HBT to 4HBT reinforces S 0 !S 1 excitation, and the distortion of the π-scaffold enhances the fluorescence quantum yield (Φ F ). In particular, 4HBT has the lowest oxidation potential (E ox 1 = 0.55 V vs. SCE) and displays red fluorescence with a Φ F value of 81 %.

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Azaarenes: 13 Ringe in einer Reihe durch Cyclopentanellierung

et al. 2022

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Eine Cyclopentanellierungsstrategie wird für den Zugang zu langen, stabilen Azaarenen vorgestellt. Buchwald-Hartwig-Kupplung von literaturbekannten di-und tetrabromierten cyclopentanelierten N,N'-Dihydrotetraazapentacenen lieferte stabile Azaarene mit bis zu 13 linear anellierten Benzolringen und einer Länge von 3.1 nm. Ihre optoelektronischen und halbleitenden Eigenschaften sowie ihre Aromatizität wurden untersucht.Lösliche, eindimensionale polycyclisch-aromatische Kohlenwasserstoffe [1] (molekulare Nanokohlenstoffe [2] ) sind monodisperse Modelle starrer Nanodrähte. [3] Es sind definierte, aufreinigbare und vollständig charakterisierte Spezies, während ihre Verwandten, die Leiterpolymere, [4] stets polydispers sind und oft Defekte enthalten. [5] Oligomere, obwohl mit zunehmender Länge eine synthetische Herausforderung, sind als Ladungsträgermaterialien von Interesse und erlauben die Untersuchung elektronischer Wechselwirkungen entlang dieser π-Systeme in Bezug auf Konjugationslänge [6] und Aromatizitätseffekte. . [7] Die einfachsten eindimensionalen molekularen Nanokohlenstoffe sind die längeren Acene. [3] Sie sind in ihrer Länge aufgrund ihrer Instabilität beschränkt. Die bisher längsten dargestellten Homologe sind Dodecacen, [8] dargestellt mittels Oberflächensynthese und Nonacen [10] (durch Flüssigphasen-und Festkörperreaktionen). [11] Zur Verringerung ihres di-und oligoradikalischen Charakters, [12] welcher für ihre Zersetzung verantwortlich ist, wurden verschiedene Anellierungsstrategien entwickelt. [6d, 7b, 13] Die Anzahl der Clar-Sextette erhöht sich durch Kombination von Acenein-heiten mit anderen kleinen Kohlenwasserstoffen, wie Perylen, 14,15] Corannulen, [15] Pyren, [5a, 13h,k, 16] Phenanthren, [13b] para-Benzochinon [17] und seine Knoevenagel-Derivate (Abbildung 1, A). [18] Synthesezugänge umfassen Kondensationsreaktionen, besonders für Stickstoff-substituierte Nanokohlenstoffe wie (B), [23a, 29] Buchwald-Hartwig-Kupplungen (C), [15] Suzuki-Kupplungen, Friedel-Crafts-Ringschlüsse (D) [28] sowie Cava-Reaktionen (A). Alternativ spalten Cycloreversio-

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Doubling the Length of the Longest Pyrene‐Pyrazinoquinoxaline Molecular Nanoribbons

Cited by 10 publications

References 72 publications

Ribbon‐Type Boron‐Doped Polycyclic Aromatic Hydrocarbons: Conformations, Dynamic Complexation and Electronic Properties

Ribbon‐Type Boron‐Doped Polycyclic Aromatic Hydrocarbons: Conformations, Dynamic Complexation and Electronic Properties

Bottom‐Up Preparation of Twisted Graphene Nanoribbons by Cu‐Catalyzed Deoxygenative Coupling

Azaarenes: 13 Ringe in einer Reihe durch Cyclopentanellierung

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