Synthesis of Graphene Nanoribbons via the Topochemical Polymerization and Subsequent Aromatization of a Diacetylene Precursor

Jordan, Robert S.; Wang, Yue; McCurdy, Ryan D.; Yeung, Michael T.; Marsh, Kristofer L.; Khan, Saeed I.; Kaner, Richard B.; Rubin, Yves

doi:10.1016/j.chempr.2016.06.010

Cited by 88 publications

(58 citation statements)

References 45 publications

(51 reference statements)

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“…Ab ig step toward the preparation of graphene nanoribbons using the topochemical polymerization strategy has been accomplished by Rubin and co-worker. [54] Starting from 1,4-bis(6-methoxymethyloxynaphthalen-2-yl)butadiyne 3, Scheme 1), they prepared polydiacetylenes 4 which, after at hermal treatment at 150-300 8 8Cf or several hours under inert atmosphere in the solid state,y ields to GNR 5. Interestingly,t he PDAi ntermediate can be deposited from asuspension on afield-effect transistors (FETs) substrate and heated directly to form the GNR that has been tested as as emiconductor.U sing ab ottom-contact configuration, ac harge mobility value of 0.15 cm 2 V À1 sw ith an I on /I off ratio of about 5w ere obtained.…”

Section: Topochemical Polymerization Of [N]ynes Derivativesmentioning

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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Section: Topochemical Polymerization Of [N]ynes Derivativesmentioning

confidence: 99%

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

et al. 2019

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“…Recently, Rubin and coworkers developed a new synthetic approach to GNRs through topochemical polymerization of butadiyne -containing monomers followed by aromatization at high temperature. 119 However, all these synthesis concepts except the AB-type D-A polymerization could only provide GNRs with lengths limited to dozens of nanometers, which still needed further efforts.…”

Section: Ab-type D-a Polymerization Toward Synthesis Of Gnrsmentioning

confidence: 99%

Diels–Alder polymerization: a versatile synthetic method toward functional polyphenylenes, ladder polymers and graphene nanoribbons

Hou

Narita

et al. 2017

Polym J

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The Diels-Alder reaction has been widely employed in synthetic organic chemistry since its discovery in 1928. The catalyst-free nature, functional group tolerance and high efficiency of the Diels-Alder reaction make it also promising for the fabrication of functional polymeric materials. In particular, a large variety of functional polyphenylenes (polymer structures mainly consisting of phenylenes) and ladderpolymers (double stranded polymers with periodic linkages connecting the strands) have been achieved by this method, showing potential applications such as polymer electrolyte membranes and gas separation. More recently, tailor-made polyphenylenes prepared by Diels-Alder polymerization have been utilized as precursors of structurally well-defined graphene nanoribbons (ribbon-shaped nanometer-wide graphene segments) with different widths, demonstrating large length (>600 nm) and tunable electronic band gaps. This article provides a comprehensive review for the use of Diels-Alder polymerization to build functional polyphenylenes, ladder-polymers and graphene nanoribbons.

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“…These values are comparable with literature standards. 1 What has really been demonstrated in this report is the utility of a new philosophy of bottom-up graphene synthesis, one where synthetic design prevails over synthetic rigor. After encountering a monomer which aligns correctly in the crystalline state, it is only necessary to apply mild heat or UV light to transform with very high efficiency a molecule with a molecular weight of 422 g/mol available on the gram scale to a precisely defined, semiconducting carbon material which can be freely deposited and patterned.…”

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confidence: 97%

Graphene Nanoribbons via Crystal Engineering

Evans

Martı́n

2016

Chem

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A new synthesis of graphene nanoribbons has been reported by Rubin and coworkers which combines the advantages of straightforward organic synthesis, intelligent crystal engineering, and high-yielding solid state transformations. 1 By carefully selecting simple aryl diyne monomer (6, Fig. 1), the authors report a crystal structure with very short intermolecular distances that favors topochemical polymerization in the crystalline state to long polydiacetylene (PDA, 7) chains. These rigid polymers can then be dispersed in an organic solvent, patterned onto a substrate and undergo full graphitization at moderate temperatures (300˚C, 8). This work represents a significant step forward as it proves that intelligent monomer design and crystal engineering can obviate the need for pyrolytic temperatures, tedious lithographic manipulation of graphene and the use of complex organic precursors and solution phase oxidative dehydrogenation.As progress accelerates to establish graphene as a post-silicon electronic material, interest has grown in the synthesis and applications of graphene nanoribbons (GNRs). 2 Two dimensional graphene sheets are ballistic conductors in all directions with a zero-energy Dirac point. For applications in transistors and related nanoelectronics, the development of a narrow but distinct bandgap in graphene is paramount. It has been established that confining the sheet in one direction to a narrow strip with a high aspect ratio offers the creation and control of a bandgap with energy inversely related to GNR width. GNRs have already shown good performance in OFET applications but the production of atomically precise ribbons on scale remains a significant barrier to the utility of nanoribbon transistors.GNRs exist in the often-explored frontier between small molecule and bulk material. From an electronics standpoint, this is where the action is. Where molecules like GNRs, Fullerenes, and monodisperse carbon nanotubes prove that confinement of materials dimensions and expansion beyond molecular architectures offers up

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Synthesis of Graphene Nanoribbons via the Topochemical Polymerization and Subsequent Aromatization of a Diacetylene Precursor

Cited by 88 publications

References 45 publications

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

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

Diels–Alder polymerization: a versatile synthetic method toward functional polyphenylenes, ladder polymers and graphene nanoribbons

Graphene Nanoribbons via Crystal Engineering

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