Reaction of Phthalocyanines with Graphene on Ir(111)

Altenburg, Simon J.; Lattelais, M.; Wang, Bin; Bocquet, Marie‐Laure; Berndt, Richard

doi:10.1021/jacs.5b05558

Cited by 41 publications

(43 citation statements)

References 63 publications

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“…The advantages of this combination of components are manifold. Pors and their synthetic analogues, Pcs, are thermally and chemically stable compounds with a rich redox chemistry that can be easily tuned by the careful choice of the metal atom in the macrocyclic cavity and/or by placing appropriate substituents at the peripheral and/or axial positions of the macrocycle . Moreover, these compounds possess an intense optical absorption in the red/near infrared (NIR) region of the solar spectrum, affording near‐perfect light‐harvesting units that are ideal components for photoelectronic devices .…”

Section: Introductionmentioning

confidence: 99%

Graphene and Carbon‐Nanotube Nanohybrids Covalently Functionalized by Porphyrins and Phthalocyanines for Optoelectronic Properties

Wang

Humphrey

et al. 2018

Advanced Materials

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In recent years, there has been a rapid growth in studies of the optoelectronic properties of graphene, carbon nanotubes (CNTs), and their derivatives. The chemical functionalization of graphene and CNTs is a key requirement for the development of this field, but it remains a significant challenge. The focus here is on recent advances in constructing nanohybrids of graphene or CNTs covalently linked to porphyrins or phthalocyanines, as well as their application in nonlinear optics. Following a summary of the syntheses of nanohybrids constructed from graphene or CNTs and porphyrins or phthalocyanines, explicit intraconjugate electronic interactions between photoexcited porphyrins/phthalocyanines and graphene/CNTs are introduced classified by energy transfer, electron transfer, and charge transfer, and their optoelectronic applications are also highlighted. The major current challenges for the development of covalently linked nanohybrids of porphyrins or phthalocyanines and carbon nanostructures are also presented.

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Section: Introductionmentioning

confidence: 99%

Graphene and Carbon‐Nanotube Nanohybrids Covalently Functionalized by Porphyrins and Phthalocyanines for Optoelectronic Properties

Wang

Humphrey

et al. 2018

Advanced Materials

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“…decided to investigate whether graphene can behave as diene or dienophile. This landmark investigation created a new subfield in the covalent functionalization of graphene, and several experimental and theoretical works have been performed to shed light into the thermodynamical and kinetics aspects of the [4+2] cycloadditions on 1D and 2D based carbon nanomaterials . Higher order [6+4] cycloaddition reactions are possible as Houk and Woodward showed as early as 1970, even though it is well known that they are much more difficult to attain than [4+2] Diels‐Alder reactions .…”

Section: Figurementioning

confidence: 99%

“…This landmark investigation created a new subfield in the covalent functionalization of graphene, and several experimental and theoretical works have been performed to shed light into the thermodynamical and kinetics aspects of the [4 + 2] cycloadditions on 1D and 2D based carbon nanomaterials. [22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] Higher order [6 + 4] cycloaddition reactions are possible as Houk and Woodward showed as early as 1970, [39] even though it is well known that they are much more difficult to attain than [4 + 2] Diels-Alder reactions. [40] Considering that graphene has an infinite p structure, that in principle may allow its participation in [6 + 4] cycloadditions, we decided to investigate if said type of cycloadditions are possible.…”

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confidence: 99%

Are [6+4] Cycloadditions onto Graphene Possible?

Denis

2017

ChemistrySelect

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Herein, we have studied the feasibility of [6+4] cycloadditions onto graphene by means of first principle calculations. In the case of perfect graphene we were unable to find a stable cycloaddition product when tropone was used as 6 π electron system. However, the reaction with tropone can be attained when the graphene sheet is modified by the presence of functional groups such as hydrogen atoms or epoxy groups. In the same line, dopants were found to favor the accomplishment of [6+4] cycloadditions. In the best scenario, for heavily hydrogenated sheets or Si doped graphene, the reactions were highly exergonic, proceed without barrier and were preferred over the [4+2] path. With regards to edges, for saturated armchair edges the reaction was endergonic but possible since a stable [6+4] cycloaddition product could be found whereas for bare armchair edges the reaction proceeds smoothly. We propose that [6+4] cycloadditions can be used as a new approach towards the selective functionalization of graphene.

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“…[8][9][10][11][12][13][14][15] However, an important challenge in using graphene for catalysis, is overcoming its inertness. There are a number of ways to facilitate reactions at the surface of graphene such as using metal substrates [14][15][16][17][18][19][20] to electronically dope graphene and in-plane doping of graphene with other elements. 12,13,21,22 For instance, pristine graphene has been shown to be inert to the dissociative adsorption of water whereas, BN doped and hydrogenated graphene is far more likely to dissociate water.…”

Section: Introductionmentioning

confidence: 99%

Exploring dissociative water adsorption on isoelectronically BN doped graphene using alchemical derivatives

Al-Hamdani

Michaelides

Lilienfeld

2017

The Journal of Chemical Physics

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The design and production of novel 2-dimensional materials have seen great progress in the last decade, prompting further exploration of the chemistry of such materials. Doping and hydrogenating graphene are an experimentally realised method of changing its surface chemistry, but there is still a great deal to be understood on how doping impacts on the adsorption of molecules. Developing this understanding is key to unlocking the potential applications of these materials. High throughput screening methods can provide particularly effective ways to explore vast chemical compositions of materials. Here, alchemical derivatives are used as a method to screen the dissociative adsorption energy of water molecules on various BN doped topologies of hydrogenated graphene. The predictions from alchemical derivatives are assessed by comparison to density functional theory. This screening method is found to predict dissociative adsorption energies that span a range of more than 2 eV, with a mean absolute error <0.1 eV. In addition, we show that the quality of such predictions can be readily assessed by examination of the Kohn-Sham highest occupied molecular orbital in the initial states. In this way, the root mean square error in the dissociative adsorption energies of water is reduced by almost an order of magnitude (down to ∼0.02 eV) after filtering out poor predictions. The findings point the way towards a reliable use of first order alchemical derivatives for efficient screening procedures.

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Reaction of Phthalocyanines with Graphene on Ir(111)

Cited by 41 publications

References 63 publications

Graphene and Carbon‐Nanotube Nanohybrids Covalently Functionalized by Porphyrins and Phthalocyanines for Optoelectronic Properties

Graphene and Carbon‐Nanotube Nanohybrids Covalently Functionalized by Porphyrins and Phthalocyanines for Optoelectronic Properties

Are [6+4] Cycloadditions onto Graphene Possible?

Exploring dissociative water adsorption on isoelectronically BN doped graphene using alchemical derivatives

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