Synthesis and characterization of 1,7-disubstituted and 1,6,7,12-tetrasubstituted perylenetetracarboxy-3,4:9,10-diimide derivatives

Queste, Mathieu; Cadiou, Cyril; Pagoaga, Bernard; Giraudet, L.; Hoffmann, Norbert

doi:10.1039/c0nj00240b

Cited by 66 publications

(48 citation statements)

References 74 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Br 4 -PTCDA molecules were synthesized following a reported method42. DBTP and Br 4 -PTCDA molecules were sublimed from a quartz crucible at sublimation temperatures of 423 and 528 K, respectively, onto the substrate held at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Graphene-like nanoribbons periodically embedded with four- and eight-membered rings

et al. 2017

View full text Add to dashboard Cite

Embedding non-hexagonal rings into sp2-hybridized carbon networks is considered a promising strategy to enrich the family of low-dimensional graphenic structures. However, non-hexagonal rings are energetically unstable compared to the hexagonal counterparts, making it challenging to embed non-hexagonal rings into carbon-based nanostructures in a controllable manner. Here, we report an on-surface synthesis of graphene-like nanoribbons with periodically embedded four- and eight-membered rings. The scanning tunnelling microscopy and atomic force microscopy study revealed that four- and eight-membered rings are formed between adjacent perylene backbones with a planar configuration. The non-hexagonal rings as a topological modification markedly change the electronic properties of the nanoribbons. The highest occupied and lowest unoccupied ribbon states are mainly distributed around the eight- and four-membered rings, respectively. The realization of graphene-like nanoribbons comprising non-hexagonal rings demonstrates a controllable route to fabricate non-hexagonal rings in nanoribbons and makes it possible to unveil their unique properties induced by non-hexagonal rings.

show abstract

Section: Methodsmentioning

confidence: 99%

Graphene-like nanoribbons periodically embedded with four- and eight-membered rings

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Rubrene (Alfa Aesar, 97%) was used as purchased. PDIB, PDIB-2OPh and PDIB-4OPh were synthesized according to procedures described in the literature 29,30,31 . All crystals were grown using the physical vapor transport (PVT) technique 32 under a stream of ultrapure Ar gas.…”

Section: Experimental Methodsmentioning

confidence: 99%

Effect of Molecular Stacking on Exciton Diffusion in Crystalline Organic Semiconductors

et al. 2015

View full text Add to dashboard Cite

Exciton diffusion is at the heart of most organic optoelectronic devices' operation, and it is currently the most limiting factor to their achieving high efficiency. It is deeply related to molecular organization, as it depends on intermolecular distances and orbital overlap. However, there is no clear guideline for how to improve exciton diffusion with regard to molecular design and structure. Here, we use single-crystal charge-transfer interfaces to probe favorable exciton diffusion. Photoresponse measurements on interfaces between perylenediimides and rubrene show a higher photocurrent yield (+50%) and extended spectral coverage (+100 nm) when there is increased dimensionality of the percolation network and stronger orbital overlap. This is achieved by very short interstack distances in different directional axes, which favors exciton diffusion by a Dexter mechanism. Even if the core of the molecule shows strong deviation from planarity, the similar electrical resistance of the different systems, planar and nonplanar, shows that electronic transport is not compromised. These results highlight the impact of molecular organization in device performance and the necessity of optimizing it to take full advantage of the materials' properties.

show abstract

“…The interest for this class of chromophores lies in their exceptional photochemical and thermal stabilities, high electron affinity and mobility, good synthetic accessibility, and the possibility to finely tune their optical and redox properties. [ ][ ] It is well known [ ][ ] that with the introduction of substituents in the bay positions of the rylene core one can significantly influence their structural and functional properties. In particular, different substituents such as amines, cyanides, halogens, aryl, or aryloxy groups have been attached at the bay positions of rylenediimides so far, [ ][ ][ ] making those substrates highly versatile molecular modules for functional materials .…”

Section: Introductionmentioning

confidence: 99%

A Twisted Bay‐Substituted Quaterrylene Phosphorescing in the NIR Spectral Region

Miletić

Fermi

Papadakis

et al. 2017

Helvetica Chimica Acta

View full text Add to dashboard Cite

The preparation of the first soluble quaterrylene derivative featuring peripheral tert‐butyl substituents and sterically hindering, core‐anchored triflate groups has been achieved. This involves a facile synthetic route based on an oxidative coupling of perylene precursors in the presence of H2O2 as oxidant. The steric hindrance between the TfO substituents at the central bay position of the quaterrylene board triggers a strong deformation of the central perylene planarity, which forces the quaterrylene platform to adopt a twisted geometry as shown by X‐ray analysis. Exceptionally, photophysical investigations show that the core‐twisted quaterrylene phosphoresces in the NIR spectral region at 1716 nm. Moreover, third‐order nonlinear optical measurements on solutions and thin film containing the relevant molecule showed very large second hyperpolarizability values, as predicted by theoretical calculations at the CAM‐B3LYP/6‐31G** level of theory, making this material very appealing for photonic applications.

show abstract

Synthesis and characterization of 1,7-disubstituted and 1,6,7,12-tetrasubstituted perylenetetracarboxy-3,4:9,10-diimide derivatives

Cited by 66 publications

References 74 publications

Graphene-like nanoribbons periodically embedded with four- and eight-membered rings

Graphene-like nanoribbons periodically embedded with four- and eight-membered rings

Effect of Molecular Stacking on Exciton Diffusion in Crystalline Organic Semiconductors

A Twisted Bay‐Substituted Quaterrylene Phosphorescing in the NIR Spectral Region

Contact Info

Product

Resources

About