“Magic” Surface Clustering of Borazines Driven by Repulsive Intermolecular Forces

Kervyn, Simon; Kalashnyk, Nataliya; Riello, Massimo; Moreton, Ben; Tasseroul, Jonathan; Jones, T. S.; Vita, Alessandro De; Costantini, Giovanni; Bonifazi, Davide

doi:10.1002/anie.201300948

Cited by 37 publications

(32 citation statements)

References 47 publications

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“…[45,46] In a collaborative venture with the groups led by Alessandro De Vita (King's College London) and Giovanni Costantini (University of Warwick), we have described the non-covalent bottomup engineering of borazine-based architectures on metal surfaces. [42] By means of low-temperature (LT) scanning tunneling microscopy (STM) measurements, we have observed different networks depending on the aryl substituents. In particular, we have shown that borazines 2 and 5 undergo different molecular organization on Cu(111) surfaces.…”

Section: Borazine Synthesismentioning

confidence: 99%

“…Synthetic onepot procedure for preparing borazines: condensation and organometallic addition steps. [40][41][42][43][44] In collaboration with the group of Prof. Franco Cacialli (UCL London), we used molecule 2 as UV-emitter in a lightemitting electrochemical cell (LEC). [41] Weak UV-emission was observed at high voltages (~15 V).…”

Section: Borazine Synthesismentioning

confidence: 99%

“…As it clearly appears from Higher resolution images (c-d) of the porous networks. [42,44] Reprinted with permission from refs [42,44]. Copyright (2013 and 2014) Wiley.…”

Section: Branched Multiborazine Nanostructuresmentioning

confidence: 99%

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Renaissance of an Old Topic: From Borazines to BN-doped Nanographenes

Lorenzo-Garcia

Bonifazi

2017

Chimia

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Graphene is one of the leading materials in today's science, but the lack of a band gap limits its application to replace semiconductors in optoelectronic devices. To overcome this limitation, the replacement of C=C bonds by isostructural and isoelectronic bonds is emerging as an effective strategy to open a band gap in monoatomic graphene layers. First prepared by Stock and Pohland in 1926, borazine is the isoelectronic and isostructural inorganic analogue of benzene, where the C=C bonds are replaced by B-N couples. The strong polarity of the BN bonds widens the molecular HOMO-LUMO gap, imparting strong UV-emission/absorption and electrical insulating properties. These properties make borazine a valuable molecular scaffold to be inserted as doping units in graphitic-based carbon materials to tailor a relevant band gap. It is with this objective that we became interested in the development of new synthetic organic methodologies to gain access to functionalized borazine derivatives. In particular, we have described the synthesis of borazine derivatives that, featuring aryl substituents at the B-centers bearing ortho-functionalities, are exceptionally stable against hydrolysis. Building on these structural motifs, we prepared hybrid BN-doped polyphenylene nanostructures featuring controlled doping patterns, both as dosage and orientation. Finally, exploiting the Friedel-Craft electrophilic aromatic substitution, we could develop the first rational synthesis of the first soluble hexa-peri-hexabenzoborazinocoronene and measured its optoelectronic properties, showing a widening of its gap compared to its full-carbon congener.

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Section: Borazine Synthesismentioning

confidence: 99%

Section: Borazine Synthesismentioning

confidence: 99%

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Renaissance of an Old Topic: From Borazines to BN-doped Nanographenes

Lorenzo-Garcia

Bonifazi

2017

Chimia

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“…Borazine containing PAHs are prone to hydrolytic decomposition which delayed the development of this eld. 43 In most cases, this reactivity is mitigated by steric bulk, 44,45 introduction of electron rich substituents or structural connement of the borazine ring. [45][46][47][48][49][50][51][52]…”

Section: Introductionmentioning

confidence: 99%

“…(a) Top view of the molecular structure of 1;44 (b) the molecular structure of 1, as determined by X-ray crystallography, overlaid (RMSD ¼ 0.0603) with the computed structure for 1 in red, translated to (x + 1/ 2, y, z + 1/2) with respect to the X-ray coordinates; (c) packing structure highlighting the CH/p and aromatic p/p interactions.9568 | Chem. Sci., 2019, 10, 9565-9570 This journal is © The Royal Society of Chemistry 2019 Chemical Science Edge Article Open Access Article.…”

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confidence: 99%

Borazatruxenes

et al. 2019

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The Chemistry of Multibonded Organoboron Compounds

Devillard

Alcaraz

2020

Patai's Chemistry of Functional Groups

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Multiply bonded boron species are fascinating objects of study addressing concerns about the chemical bonding. Although mostly exemplified with light p‐block elements, the use of Group 6–10 transition metals as models to more clearly understand and rationalize the bonding in this family of compounds has also proved successful. In this prospect, the interplay between experiment and theory pushes forward the frontiers of the analysis based on the metric parameters, and it clearly appears that the notion of doubly or triply bonded boron in such species must be qualified. The bond orders are more often partial involving more or less polarized bonds responsible for the chemical reactivity. These features are developed in this chapter starting with the nearest neighbors of boron and finishing with the case of transition metals.

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“Magic” Surface Clustering of Borazines Driven by Repulsive Intermolecular Forces

Cited by 37 publications

References 47 publications

Renaissance of an Old Topic: From Borazines to BN-doped Nanographenes

Renaissance of an Old Topic: From Borazines to BN-doped Nanographenes

Borazatruxenes

The Chemistry of Multibonded Organoboron Compounds

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