Correction: A computational exploration of the crystal energy and charge-carrier mobility landscapes of the chiral [6]helicene molecule

Rice, Beth; LeBlanc, Luc M.; Otero-de-la-Roza, Alberto; Fuchter, Matthew J.; Johnson, Erin R.; Nelson, Jenny; Jelfs, Kim E.

doi:10.1039/c8nr90093k

Cited by 5 publications

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“…In TES‐Pn, J max is equal to J max in 16 ; the lower hole mobility is largely related to a higher λ ( λ inner =142 meV). The maximum hole mobility of 3.75 cm 2 V −1 s −1 in 16 exceeds all hole mobilities for helicenes previously computed (i) aza[6]helicene regioisomers ( λ outer =0.30 eV) 0.02–0.26 cm 2 V −1 s −1 ; [27] (ii) carbo[6]helicene ( λ outer =0.14 eV) 0.00–2.00 cm 2 V −1 s −1 ; [11b,c] (iii) (rac)‐aza[6]helicene 0.06 cm 2 V −1 s −1 and (+)‐aza[6]helicene 0.03 cm 2 V −1 s −1 [11a] . Those helicenes generally show smaller hole transfer integrals and larger λ intra (hole) as would be expected for smaller molecules.…”

Section: Resultsmentioning

confidence: 53%

“…[8] Spin-filtering properties of chiral compounds,k nown as the chirality induced spin selectivity effect (CISS-effect), [9] render helicenes intriguing targets for spin dependent applications [10] like spintronics.F inally,h elicity is au seful tool to fine-tune the parameters for organic materials,asmixtures of enantiomers in different ratios lead to varying solid-state packings and, therefore,d ifferent properties. [11] Form any of these purposes,such as optical and electronic applications,the p-extension of helicenes is beneficial due to the strong visible light absorption and fluorescence,t unable semiconducting properties,and aggregation of large p-systems.…”

Section: Introductionmentioning

confidence: 99%

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A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems

et al. 2021

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Incorporating helicity into large polycyclic aromatic hydrocarbons (PAHs) constitutes a new field of research at the interface between chemistry and material sciences. Lately, interest in the design of π-extended helicenes has surged. This new class of twisted, chiral nanographenes not only reveals unique characteristics but also finds its way into emerging applications such as spintronics. Insights into their structure-property relationships and on-demand tuning are scarce. To close these knowledge gaps, we designed a straightforward synthetic route towards a full-fledged family of πextended helicenes: superhelicenes. Common are two hexa-perihexabenzocoronenes (HBCs) connected via a central 5-membered ring. By means of structurally altering this 5-membered ring, we realized a versatile library of molecular building blocks. Not only the superhelicene structure, but also their features are tuned with ease. In-depth physico-chemical characterizations served as a proof of concept thereof. The superhelicene enantiomers were separated, their circular dichroism was measured in preliminary studies and concluded with an enantiomeric assignment. Our work was roundedoff by crystal structure analyses. Mixed stacks of M-and P-isomers led to twisted molecular wires. Using such stacks, charge-carrier mobilities were calculated, giving reason to expect outstanding hole transporting properties.

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Section: Resultsmentioning

confidence: 53%

Section: Introductionmentioning

confidence: 99%

A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems

et al. 2021

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“…In TES‐Pn, J max is equal to J max in 16 ; the lower hole mobility is largely related to a higher λ ( λ inner =142 meV). The maximum hole mobility of 3.75 cm 2 V −1 s −1 in 16 exceeds all hole mobilities for helicenes previously computed (i) aza[6]helicene regioisomers ( λ outer =0.30 eV) 0.02–0.26 cm 2 V −1 s −1 ; [27] (ii) carbo[6]helicene ( λ outer =0.14 eV) 0.00–2.00 cm 2 V −1 s −1 ;[ 11b , 11c ] (iii) (rac)‐aza[6]helicene 0.06 cm 2 V −1 s −1 and (+)‐aza[6]helicene 0.03 cm 2 V −1 s −1 . [11a] Those helicenes generally show smaller hole transfer integrals and larger λ intra (hole) as would be expected for smaller molecules.…”

Section: Resultsmentioning

confidence: 59%

A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems

et al. 2021

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We designed as traightforwards ynthetic route towards af ull-fledged family of p-extended helicenes:s uperhelicenes.T hey have two hexa-peri-hexabenzocoronenes (HBCs) in common that are connected via ac entral fivemembered ring. By means of structurally altering this 5membered ring, we realized av ersatile library of molecular building blocks.Not only the superhelicene structure,but also their features are tuned with ease.I n-depth physico-chemical characterizations served as ap roof of concept thereof.T he superhelicene enantiomers were separated, their circular dichroism was measured in preliminary studies and concluded with an enantiomeric assignment. Our work was rounded-off by crystal structure analyses.Mixed stacks of M-and P-isomers led to twisted molecular wires.U sing such stacks,c hargecarrier mobilities were calculated, giving reason to expect outstanding hole transporting properties.

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“…25 Previously, we performed CSP studies to predict the carbo [6]helicene and aza [6]helicene crystal-energy landscapes and found that the chirality of the crystal (enantiopure vs. racemic) can drastically affect the corresponding charge-carrier mobilities. 31,32 For carbo [6]helicene, we structurally classified polymorphs into recurring packing motifs. A particular 'translational motif' (Figure 1c) was found with the highest probability across the entire crystal-energy landscape, being observed in 63% of the hypothetical low-energy polymorphs.…”

Section: Introductionmentioning

confidence: 99%

“…A particular 'translational motif' (Figure 1c) was found with the highest probability across the entire crystal-energy landscape, being observed in 63% of the hypothetical low-energy polymorphs. 32 Most recently, Salerno et al studied the effect of the nitrogen substitution position on charge transport for the most commonly observed [6]helicene crystal structure (CSD code: HEXHEL, Figure 1b), 33 and found that this same 'translational motif' gave rise to the highest electron-transfer integrals across the majority of aza [6]helicene isomers.…”

Section: Introductionmentioning

confidence: 99%

Computational Screening of Organic Semiconductors: Exploring Side-Group Functionalisation and Assembly to Optimise Charge Transport in Chiral Molecules

Schmidt¹,

Weatherby²,

Sugden³

et al. 2021

Preprint

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Molecular materials are challenging to design as their packing arrangement and hence properties are subject to subtle variations in the interplay of soft intermolecular interactions that are difficult to predict. The rational design of new molecular materials with tailored properties is currently hampered by the lack of knowledge of how a candidate molecule will pack in space and how we can control the polymorphs we can experimentally obtain. Here, we develop a simplified approach to aid the material design process, by the development of a screening process that is used to test 1344 helicene molecules that have potential as organic electronic materials. Our approach bridges the gap between single molecule design, molecular assembly, and the resulting charge-carrier mobilities. We find that fluorination significantly improves electron transport in the molecular material by up to 200%; the reference [6]helicene packing showed a mobility of 0.30 cm2 V-1 s-1, fluorination increased the mobility to up to 0.96 and 0.97 (13-fluoro[6]H and 4,13-difluoro[6]H), assuming an outer reorganisation energy of 0.30 eV. Side groups containing triple bonds largely lead to improved transfer integrals. We validate our screening approach through the use of crystal structure prediction to confirm the presence of favourable packing motifs to maximize charge mobility.

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Correction: A computational exploration of the crystal energy and charge-carrier mobility landscapes of the chiral [6]helicene molecule

Abstract: Correction for 'A computational exploration of the crystal energy and charge-carrier mobility landscapes of the chiral [6]helicene molecule' by Beth Rice et al., Nanoscale, 2018, 10, 1865-1876.

Cited by 5 publications

References 0 publications

A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems

A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems

A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems

Computational Screening of Organic Semiconductors: Exploring Side-Group Functionalisation and Assembly to Optimise Charge Transport in Chiral Molecules

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