Nanographene and Graphene Nanoribbon Synthesis via Alkyne Benzannulations

Senese, Amber D.; Chalifoux, Wesley A.

doi:10.3390/molecules24010118

Cited by 64 publications

(55 citation statements)

References 129 publications

(204 reference statements)

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“…This method was also employed to furnish a series of larger PAHs, such as chrysene 52 and picene 54 [108]. Another widely used method is alkyne cyclization promoted by electrophilic reagents (Figure 11(c)) [109]. For example, Larock et al [110] reported ICl-induced intramolecular cyclization of 2-(arylethynyl)biphenyls (e.g., 55), providing PAHs with iodo groups, which can be used for further functionalizations.…”

Section: π-Extension With Extra Carbons and Ringsmentioning

confidence: 99%

Polycyclic aromatic hydrocarbons in the graphene era

2019

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Polycyclic aromatic hydrocarbons (PAHs) have been the subject of interdisciplinary research in the fields of chemistry, physics, materials science, and biology. Notably, PAHs have drawn increasing attention since the discovery of graphene, which has been regarded as the "wonder" material in the 21st century. Different from semimetallic graphene, nanoscale graphenes, such as graphene nanoribbons and graphene quantum dots, exhibit finite band gaps owing to the quantum confinement, making them attractive semiconductors for next-generation electronic applications. Researches based on PAHs and graphenes have expanded rapidly over the past decade, thereby posing a challenge in conducting a comprehensive review. This study aims to interconnect the fields of PAHs and graphenes, which have mainly been discussed separately. In particular, by selecting representative examples, we explain how these two domains can stimulate each other. We hope that this integrated approach can offer new opportunities and further promote synergistic developments in these fields.

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Section: π-Extension With Extra Carbons and Ringsmentioning

confidence: 99%

Polycyclic aromatic hydrocarbons in the graphene era

2019

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“…[60] Ad etailed review about this reaction and the different conditions used has been recently published. [61] An example of the use of the intramolecular alkyne benzannulation for the synthesis of alow band gap GNR has been reported by Chalifouxsg roup in 2016. [62] Starting from ap oly(p-phenylene) with properly located alkyne moieties (10), they used am odified version of the Swagersi ntramolecular, acid-promoted electrophilic cyclization to obtain asoluble [5] A GNR 11.Atfirst, TFAwas used as the Bronsted acid, but only one cyclization proceeded due to the rigidification of the polymer backbone,r esulting in am uch higher barrier for the second cyclization.Astronger acid, trifluoromethanesulfonic acid (CF 3 SO 3 H), was needed to fully complete the second cyclization.A ne xcess of TFA (100 equivalents) leads to only traces of the doubly cyclized product, even after two days.When only CF 3 SO 3 Hwas used, side products and lower yields was observed.…”

Section: Alkyne Benzannulationmentioning

confidence: 99%

Emerging Bottom‐Up Strategies for the Synthesis of Graphene Nanoribbons and Related Structures

et al. 2019

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The solution‐phase synthesis is one of the most promising strategies for the preparation of well‐defined graphene nanoribbons (GNRs) in large scale. To prepare high quality, defect‐free GNRs, cycloaromatization reactions need to be very efficient, proceed without side reaction and mild enough to accommodate the presence of various functional groups. In this Minireview, we present the latest synthetic approaches for the synthesis of GNRs and related structures, including alkyne benzannulation, photochemical cyclodehydrohalogenation, Mallory and Pd‐ and Ni‐catalyzed reactions.

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“…Chalifoux and coworkers recently used a bay‐region‐selective alkyne benzannulation reaction on different small PAHs to prepare nanographenes whose absorption spectra extend to the red region . Starting from properly functionalized pyrenes, they prepared pero‐ and teropyrene derivatives through a four‐fold benzannulation reaction using either InCl 3 or a Brönsted acid as the catalyst (Figure ) .…”

Section: Nanographenes and Graphene Nanoribbonsmentioning

confidence: 99%

Polycyclic Aromatic Hydrocarbons as Potential Building Blocks for Organic Solar Cells

Aumaître

Morin

2019

The Chemical Record

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Since the discovery of graphene in the early 2000′s, polycyclic aromatic hydrocarbons (PAHs) have been resurrected and new synthetic tools have been developed to prepare unprecedented structures with unique properties. One application that has been overlooked for this class of molecules is organic solar cells (OSCs). In this account, we present the recent development in the preparation of moderate to low band gap PAHs that could potentially be used as semiconducting materials in OSCs. Our focus is directed toward all‐carbon PAHs as well as their polymeric analogs.

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Nanographene and Graphene Nanoribbon Synthesis via Alkyne Benzannulations

Cited by 64 publications

References 129 publications

Polycyclic aromatic hydrocarbons in the graphene era

Polycyclic aromatic hydrocarbons in the graphene era

Emerging Bottom‐Up Strategies for the Synthesis of Graphene Nanoribbons and Related Structures

Polycyclic Aromatic Hydrocarbons as Potential Building Blocks for Organic Solar Cells

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