Using a Photoacid Generator to Switch the Direction of Electronic Energy Transfer in a Molecular Triad

Hablot, Delphine; Harriman, Anthony; Ziessel, Raymond

doi:10.1002/anie.201102065

Cited by 25 publications

(13 citation statements)

References 30 publications

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“…Hablot et al [21] presented another example of ionic effect using a triad system comprising of two disparate bodipy units connected with a central pyrrolyl derivative core that absorbs and emits at a higher energy than either termini. The design principle is based on the possibility to switch the intramolecular EET flow by the protonation at the amine sites of one of the terminals, as shown in Figure 3.…”

Section: Interaction With Ionsmentioning

confidence: 99%

Recent advances in artificial photosynthetic systems at Newcastle University

Farràs

Cucinotta

2017

Comptes Rendus Chimie

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This review covers the most significant research done by the grouping of scientists working at Newcastle University during the last five years in the area of artificial photosynthesis. In particular, it tackles aspects of light harvesting in molecular systems and solid state materials, photocatalysis in homogeneous and heterogenous phase, and the fabrication of photoelectrochemical devices for the generation of hydrogen.

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Section: Interaction With Ionsmentioning

confidence: 99%

Recent advances in artificial photosynthetic systems at Newcastle University

Farràs

Cucinotta

2017

Comptes Rendus Chimie

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“…These optical transitions are safely assigned, in the light of previous studies, 15 to the S 0 →S 1 transition of the DPP chromophores. 28,29 The weak transition about 460 nm, which is more pronounced in the presence of two TPA fragments in 7 (ε ca. 20,000 M -1 cm -1 ) compared with 5 (ε ca.…”

Section: Letter Syn Lettmentioning

confidence: 99%

Panchromatic Push–Pull Dyes of Elongated Form from Triphenylamine, Diketopyrrolopyrrole, and Tetracyanobutadiene Modules

Heyer

Ziessel

2015

Synlett

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Several symmetrical and unsymmetrical thiophene-functionalized diketopyrrolopyrrole chromophores bearing a bis(p-methoxyphenyl)-p-phenylamine substituent were synthesized through palladium-catalyzed cross-coupling reactions. Mono-substitution and di-substitution occur using either alkyne or borolane groups, allowing the preparation of mixed systems. The alkyne derivatives could be prepared in high yields, and are versatile building blocks for the [2+2] cycloaddition of tetracyanoethylene, leading to 1,1,4,4-tetracyanobuta-1,3-diene derivatives. These interesting push-pull molecules exhibit a rich redox activity, which is understandable in light of the behavior of appropriate reference compounds. These innovative and rationally designed scaffolds are highly colored, exhibiting high absorption coefficients and spanning an absorption range of more than 600 nm of the UV/Vis electromagnetic spectrum.Highly dipolar donor-acceptor substituted systems (also called push-pull chromophores) are a fascinating set of synthetic targets that have a wide range of properties such as nonlinear optical (NLO) responses, significant two-photon absorption cross-sections for doubling the frequency of incident radiation, charge transport and charge separation abilities. 1 Potential applications of such sophisticated dyes for fluorescence enhancement, advanced microscopy techniques, biomedical analysis, 2 and for the construction of both organic photovoltaic materials 3 and field-effect transistors, 4 are foreseen.An impressive number of donor groups are used in the design of push-pull systems and the complete list is too large to detail; however, among them, symmetric or dissymmetric triarylamines hold the lead. 5 Similarly, electronwithdrawing groups are numerous, with the most used being nitro-and cyano-(or polycyano) modules, which are suitable for promoting charge-transfer or electron-transfer along the main molecular axis. 6 Of the common dyes, diketopyrrolopyrroles (DPPs) based on a bis-lactam backbone are interesting in regard to their synthetic availability, ease of modification, outstanding robustness, and attractive spectroscopic properties, making them excellent building blocks for a myriad of applications. 7 These chromophores are well known for their strong absorption bands in the UV/Vis region, high solubility in common organic solvents when adequately substituted on the bis-lactam core, high fluorescence quantum yields, and relatively long excited-state lifetimes (1-5 ns). These properties make DPPs promising candidates for OPV applications, 8,9 and for the engineering of dinuclear boron(III) complexes displaying unusual spectral properties. 10 Moreover, the construction of a push-pull system upon the DPP scaffold should engender some new properties, such as photochromism, enhanced charge transport, and recombination of π-conjugated electronic states. These could provide the basis for new developments in organic photovoltaic devices and fluorescent probes for biomedical applications. 11 Water-soluble conjugated and mul...

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“…Related research has used fullerenes decorated with disparate Bodipy dyes [17] and examined different types of spacer group [18]. The direction of EET along the molecular axis can be switched by rapid protonation of the terminal acceptor using a photo-acid [19]. The mechanism of the EET process has been resolved in many cases, while the relative contributions of coulombic EET and electron exchange have been delineated by high-pressure techniques [20].…”

Section: Artificial Light-harvesting Systemsmentioning

confidence: 99%

Providing power for miniaturized medical implants: triplet sensitization of semiconductor surfaces

Benniston

Harriman

Yang

2013

Phil. Trans. R. Soc. A.

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Here, we recognize the growing significance of miniaturized devices as medical diagnostic tools and highlight the need to provide a convenient means of powering such instruments when implanted into the body. One of the most promising approaches to this end involves using a light-collection facility to absorb incident white light and transfer the photonic energy to a tiny semiconductor embedded on the device. Although fluorescent organic molecules offer strong potential as modules for such solar collectors, we emphasize the promise offered by transition metal complexes. Thus, an extended series of binuclear Ru(II)/Os(II) poly(pyridine) complexes has been shown to be highly promising sensitizers for amorphous silicon solar cells. These materials absorb a high fraction of visible light while the Ru(II)-based units possess triplet energies that are comparable to those of the naphthalene-based bridge. The metal complex injects a triplet exciton into the bridge and this, in turn, is trapped by the Os(II)-based terminal. The result is extremely efficacious triplet-energy transfer; at room temperature the rate of energy transfer is independent of distance over some 6 nm and only weakly dependent on temperature.

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Using a Photoacid Generator to Switch the Direction of Electronic Energy Transfer in a Molecular Triad

Cited by 25 publications

References 30 publications

Recent advances in artificial photosynthetic systems at Newcastle University

Recent advances in artificial photosynthetic systems at Newcastle University

Panchromatic Push–Pull Dyes of Elongated Form from Triphenylamine, Diketopyrrolopyrrole, and Tetracyanobutadiene Modules

Providing power for miniaturized medical implants: triplet sensitization of semiconductor surfaces

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