Electrochemical and optical properties of molecular triads based on triphenylamine, diketopyrrolopyrrole and boron-dipyrromethene

Ruff, Adrian; Heyer, Elodie; Roland, Thomas; Haacke, S.; Ziessel, Raymond; Ludwigs, Sabine

doi:10.1016/j.electacta.2015.05.093

Cited by 20 publications

(17 citation statements)

References 51 publications

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“…1 and 6). It should be noted that the results reported here for EtHex-DPP-T1 in solution are very similar to those presented for thin layers of very similar compounds, recently reported in the literature [15]. In Table 2, l max of bands characteristic of the neutral and ionic forms of the studied compounds are collected.…”

Section: Resultssupporting

confidence: 73%

“…For EtHex-DPP-T1, only the spectra of the radical cation form could be registered, consistent with partial irreversibility of the second oxidation peak in its differential pulse voltammogram (see Fig. 1) and the recent report on the spectroelectrochemical investigations of thin films of a very similar compound [15]. In the remaining three cases the spectroelectrochemical response can be clearly correlated with differential pulse voltammetry.…”

Section: Resultssupporting

confidence: 72%

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EPR and UV–vis spectroelectrochemical studies of diketopyrrolopyrroles disubstituted with alkylated thiophenes

et al. 2016

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Section: Resultssupporting

confidence: 73%

Section: Resultssupporting

confidence: 72%

EPR and UV–vis spectroelectrochemical studies of diketopyrrolopyrroles disubstituted with alkylated thiophenes

et al. 2016

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“…Were excimer states a major population, the fluorescence would be dominated by the red‐shifted, broad emission seen in our previous thin film study of TDPP . Weaker NIR bands corresponding to the TDPP IP have been measured using spectroelectrochemistry at λ =831, 855, and 937 nm, so some absorption in the NIR is to be expected in this molecular system that can easily take on charge transfer character. However, similar to the steady state results, we find that any spectroscopic contribution from excimer species in TDPP2 is negligible.…”

Section: Resultssupporting

confidence: 70%

“…has a broad absorption centered at 605 nm with a sharp absorption band for TDPP −. at 636 nm . For TDPP2 in PrCN, the feature at 640 nm is dominant by 25 ps, when the GSB begins to decay along with the peak at 640 nm.…”

Section: Resultsmentioning

confidence: 84%

Charge‐Transfer Character in a Covalent Diketopyrrolopyrrole Dimer: Implications for Singlet Fission

et al. 2017

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Diketopyrrolopyrrole (DPP) is a strongly absorbing, photostable chromophore that can undergo singlet fission (SF), a photophysical process that promises to significantly enhance solar‐cell performance. In the solid state, DPP packs in a herringbone arrangement that maximizes intermolecular donor–acceptor interactions, suggesting that charge‐transfer (CT) states play a role in DPP SF. In order to characterize intermolecular DPP CT states in molecular assemblies, we have synthesized a covalent DPP dimer bridged by a xanthene linker, which places two thiophene‐substituted DPPs (TDPPs) in a cofacial arrangement that mimics chromophore π–π stacking in the thin film. After photoexcitation in polar solvents, symmetry‐breaking charge separation forms the fully charge separated TDPP+.–TDPP−. ion‐pair state. In nonpolar solvents, charge separation is incomplete leading to the TDPPδ+–TDPPδ− CT state, which is in pseudoequilibrium with the relaxed S1S0 state observed by transient absorption and emission spectroscopy. This study highlights the importance of intramolecular coupling as well as the importance of entropy to promoting SF in chromophore dimers for which SF is endo‐ or isoergic.

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“…22 Clearly, the highest occupied molecular orbital (HOMO) of the triad is located on the BODIPY part of the triad (−5.45 eV). The anodic part of the cyclovoltamogramm revealed two reversible processes at −1.08 and −1.17 V and an irreversible process at −1.72 V. By comparison with nonsubstituted BODIPY and DPPTh dyes, the first reduction potential was taken to be localized on the DPPTh fragment of the triad, enabling assignment of the energy of the lowest unoccupied molecular orbital (LUMO) as −3.70 eV.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Step-by-Step Synthesis of Multimodule Assemblies Engineered from BODIPY, DPP, and Triphenylamine Moieties

Heyer

Ziessel

2015

J. Org. Chem.

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In the present account we describe unsymmetrical triads constructed from extended borondipyrromethene (BODIPY) dyes, diketopyrrolopyrrole (DPP) dyes, and electron donor fragments based on triarylamine. The assemblages are such that each module maintains its individual optical and redox properties. The use of phenyl-alkyne-phenyl or phenyl-alkyne-thienyl spacer units is favorable for weak electronic interaction between the modules. The step-by-step linking of each module using palladium-catalyzed cross-coupling reactions provides both mono- and disubstituted derivatives, the latter obtained by passing in particular through a pivotal monosubstituted DPP building block with a reactive bromo substituent. Thus, grafting of a second dye occurs in a controlled manner, providing the target triads in good yields. This protocol allows also the synthesis of key intermediates and dyads, which appear useful for the understanding of the electrochemical and spectroscopic properties. All the dyes exhibit redox and optical properties suitable for cascade energy transfer and photoinduced electron transfer processes in appropriate solvents.

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Electrochemical and optical properties of molecular triads based on triphenylamine, diketopyrrolopyrrole and boron-dipyrromethene

Cited by 20 publications

References 51 publications

EPR and UV–vis spectroelectrochemical studies of diketopyrrolopyrroles disubstituted with alkylated thiophenes

EPR and UV–vis spectroelectrochemical studies of diketopyrrolopyrroles disubstituted with alkylated thiophenes

Charge‐Transfer Character in a Covalent Diketopyrrolopyrrole Dimer: Implications for Singlet Fission

Step-by-Step Synthesis of Multimodule Assemblies Engineered from BODIPY, DPP, and Triphenylamine Moieties

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