A Bichromophore Based on Perylene and Terrylene for Energy Transfer Studies at the Single-Molecule Level

Schlichting, P.; Duchscherer, Bettina; Seisenberger, Georg; Basché, Thomas; Bräuchle, Christoph; Müllen, Kläus

doi:10.1002/(sici)1521-3765(19990802)5:8<2388::aid-chem2388>3.0.co;2-2

Cited by 41 publications

(3 citation statements)

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“…Up to now, higher order rylenes such as terrylene, quaterrylene, pentarylene and hexarylene and their dicarboxylic imide derivatives have been synthesized. [ ][ ] Among these, rylenediimides received a lot of attention for their application as light‐harvesting materials, organic electronics, photovoltaics, and biomedical sensors among others. 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.…”

Section: Introductionmentioning

confidence: 99%

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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Section: Introductionmentioning

confidence: 99%

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

Miletić

Fermi

Papadakis

et al. 2017

Helvetica Chimica Acta

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“…Even though in bulk the fluorescence intensity of the dyads was significantly increased in comparison to the simple DAOTA dyes, we wanted to see how these dyads act as single molecule emitters. − Figure shows the dyads and the PMI/PDI reference compounds immobilized in a PMMA thin film. The scanning confocal fluorescence microscopy images in Figure clearly show that intensitywise the dyads (B and E) are as bright as corresponding single PMI or PDI molecules (A and D).…”

Section: Results and Discussionmentioning

confidence: 99%

Rational Design of Bright Long Fluorescence Lifetime Dyad Fluorophores for Single Molecule Imaging and Detection

et al. 2021

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Increasing demand for detecting single molecules in challenging environments has raised the bar for the fluorophores used. To achieve better resolution and/or contrast in fluorescence microscopy, it is now essential to use bright and stable dyes with tailored photophysical properties. While long fluorescence lifetime fluorophores offer many advantages in time-resolved imaging, their inherently lower molar absorption coefficient has limited applications in single molecule imaging. Here we propose a generic approach to prepare bright, long fluorescence lifetime dyad fluorophores comprising an absorbing antenna chromophore with high absorption coefficient linked to an acceptor emitter with a long fluorescence lifetime. We introduce a dyad consisting of a perylene antenna and a triangulenium emitter with 100% energy transfer from donor to acceptor. The dyad retained the long fluorescence lifetime (∼17 ns) and high quantum yield (75%) of the triangulenium emitter, while the perylene antenna increased the molar absorption coefficient (up to 5 times) in comparison to the free triangulenium dye. These triangulenium based dyads with significantly improved brightness can now be detected at the single molecule level and easily discriminated from bright autofluorescence by time-gated and other lifetime-based detection schemes.

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“…Terrylenediimide (TDI) (Scheme ) and its imide derivatives are superb polyaromatic hydrocarbon (PAH) colorants and have attracted intense research interests as functional dyes widely used in various fields, such as photovoltaic devices, nanoreporters, biolabeling, and light-harvesting systems . They have been particularly successful for single-molecule investigations due to high photostability and fluorescent quantum yield. , Meanwhile, the photo-oxidation of TDI by single oxygen 1 O 2 has been utilized to develop a sensitive and specific single-molecule method detecting 1 O 2 .…”

Section: Introductionmentioning

confidence: 99%

Fluorescence Products from Terrylenediimide with Singlet Oxygen: Red, Green, and Near-Infrared Emission

et al. 2016

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The rich photo-oxidation pathways and products of terrylenediimide (TDI) with singlet oxygen ((1)O2) have been examined by powerful computational approaches. Potential energy profiles and product fluorescence properties are characterized. A variety of new products are unraveled and predicted to emit fluorescence at both visible and near-infrared ranges, which could open the possibility for interesting applications of using TDI as a fluorescence probe for the single-molecule detection of (1)O2 and designing multicolor photoconvertible fluorophores based on (1)O2 oxidation.

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A Bichromophore Based on Perylene and Terrylene for Energy Transfer Studies at the Single-Molecule Level

Cited by 41 publications

References 0 publications

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

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

Rational Design of Bright Long Fluorescence Lifetime Dyad Fluorophores for Single Molecule Imaging and Detection

Fluorescence Products from Terrylenediimide with Singlet Oxygen: Red, Green, and Near-Infrared Emission

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