Processable Rylene Diimide Dyes up to 4 nm in Length: Synthesis and STM Visualization

Yuan, Zhongyi; Lee, Shern‐Long; Chen, Long; Li, Chen; Mali, Kunal S.; Feyter, Steven De; Müllen, Kläus

doi:10.1002/chem.201302086

Cited by 65 publications

(69 citation statements)

References 74 publications

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“…The same trend is also observed for perylenol 2 , its singly linked dimer 4 , and compounds 6 Fur and 6 Pp , which show largely tunable absorption and emission energies that lie in the red spectral region for the O‐annulated derivatives (Figure 6 b). Comparing with reports in the literature on all‐carbon PAHs exhibiting comparable visible absorption energies,68, 69, 70, 71 the results of our steady‐state studies suggest that, although it provides significant bathochromic shifts, C−O planarization does not dramatically suppress the emission quantum yields, as opposed to the formation of the C−C bonds in planar rylenes, which usually show strong absorptivities but faint luminescence 72, 73…”

Section: Resultssupporting

confidence: 78%

Tailoring Colors by O Annulation of Polycyclic Aromatic Hydrocarbons

Miletić

Fermi

Orfanos

et al. 2017

Chemistry A European J

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The synthesis of O‐doped polyaromatic hydro‐ carbons in which two polycyclic aromatic hydrocarbon sub units are bridged through one or two O atoms has been achieved. This includes high‐yield ring‐closure key steps that, depending on the reaction conditions, result in the formation of furanyl or pyranopyranyl linkages through intramolecular C−O bond formation. Comprehensive photophysical measurements in solution showed that these compounds have exceptionally high emission yields and tunable absorption properties throughout the UV/Vis spectral region. Electrochemical investigations showed that in all cases O annulation increases the electron‐donor capabilities by raising the HOMO energy level, whereas the LUMO energy level is less affected. Moreover, third‐order nonlinear optical (NLO) measurements on solutions or thin films containing the dyes showed very good values of the second hyperpolarizability. Importantly, poly(methyl methacrylate) films containing the pyranopyranyl derivatives exhibited weak linear absorption and NLO absorption compared to the nonlinearity and NLO refraction, respectively, and thus revealed them to be exceptional organic materials for photonic devices.

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Section: Resultssupporting

confidence: 78%

Tailoring Colors by O Annulation of Polycyclic Aromatic Hydrocarbons

Miletić

Fermi

Orfanos

et al. 2017

Chemistry A European J

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“…This is likely to be caused by the presence of triflate substituents, which can undergo an elimination reaction and give rise to irreversible transformations. As previously observed for other rylenes, [ ][ ] the oxidation potentials are decreasing upon increasing the π ‐extension of the aromatic scaffold (see molecules 6 and 1 ), while the presence of the strong electron‐withdrawing triflate substituents tends to deplete the electronic density of the π ‐cloud. Taken all together, these data allowed us to estimate the energy of the HOMO‐LUMO gap of molecule 1 ( Fig.…”

Section: Resultssupporting

confidence: 69%

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

Miletić

Fermi

Papadakis

et al. 2017

Helvetica Chimica Acta

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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.

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“…Quinonediimine (QDI, 1c) was found to form two different patterns of 2D crystals, the relative abundance of which could also be controlled by shear flow. 7,16 As to optical detection, Christoph Bräuchle and Thomas Basché have shown terrylene diimide (TDI, 1b) to be an ideal chromophore for SMS due to its high 21 fluorescence quantum yield and its emission above 700 nm, which made it applicable as a tracking molecule for biological studies. 7,[17][18][19] The main advantage of TDI (1b) and its analogues over other dyes, some of which may be commercially available, is their extremely high photostability.…”

Section: Rylene Chromophoresmentioning

confidence: 99%

Evolution of Graphene Molecules: Structural and Functional Complexity as Driving Forces behind Nanoscience

2014

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Abstract:The evolution of nanoscience is based on the ability of the fields of chemistry and physics to share competencies through mutually beneficial collaborations. With this in mind, in this Perspective, I describe three classes of compounds: rylene dyes, polyphenylene dendrimers, as well as nanographene molecules and graphene nanoribbons, which have provided a superb platform to nurture these relationships. The synthesis of these complex structures is demanding, but also rewarding because they stimulate unique investigations at the singlemolecule level by scanning tunneling microscopy and single-molecule spectroscopy. There are close functional and structural relationships between the molecules chosen. In particular, rylenes and nanographenes can be regarded as honeycombtype, discoid species composed of fused benzene rings. The benzene ring can thus be regarded as a universal modular building block. Polyphenylene dendrimers serve, first, as a scaffold for dyes en route to multichromophoric systems and, second, as chemical precursors for graphene synthesis. Through chemical design, it is possible to tune the properties of these systems at the single-molecule level and to achieve nanoscale control over their self-assembly to form multifunctional (nano)materials.

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Processable Rylene Diimide Dyes up to 4 nm in Length: Synthesis and STM Visualization

Cited by 65 publications

References 74 publications

Tailoring Colors by O Annulation of Polycyclic Aromatic Hydrocarbons

Tailoring Colors by O Annulation of Polycyclic Aromatic Hydrocarbons

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

Evolution of Graphene Molecules: Structural and Functional Complexity as Driving Forces behind Nanoscience

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