Macrocyclic Donor–Acceptor Dyads Composed of a Perylene Bisimide Dye Surrounded by Oligothiophene Bridges

Bold, Kevin; Stolte, Matthias; Shoyama, Kazutaka; Holzapfel, Marco; Schmiedel, Alexander; Lambert, Christoph; Würthner, Frank

doi:10.1002/ange.202113598

Cited by 13 publications

(51 citation statements)

References 73 publications

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“…In the CV (Figure 4a) reversibility of all involved redox processes can be monitored. Two reversible reduction waves corresponding to the anionic and dianionic PBI chromophore at around −1.00 V ( E red,1 ) and −1.20 V ( E red,2 ) were detected for all macrocycles (Table 1), which are in very good agreement to Ref ‐ PBI (−0.99 V/−1.19 V) [16] . In contrast, the oxidation events differ greatly within the series.…”

Section: Resultssupporting

confidence: 71%

“… Excerpt of the 1 H NMR spectra of 4T ‐ PBI , 5T ‐ PBI , [16] 6T ‐ PBI and 7T ‐ PBI (from bottom to top) in CD 2 Cl 2 at room temperature.…”

Section: Resultsmentioning

confidence: 99%

“…Even greater differences within the macrocyclic series can be observed by comparing the second oxidation potentials of 4T ‐ PBI ( E ox,2 = 0.80 V) with the other macrocycles 5T ‐ PBI [16] to 7T ‐ PBI ( E ox,2 =+0.46 V to +0.50 V). Here, especially the potential difference ( E ox,2 – E ox,1 , Table 1) between the cationic and dicationic states shall be highlighted, which is best viewed in the DPV spectra with a higher resolution of the individual waves (Figure 4b).…”

Section: Resultsmentioning

confidence: 99%

“…As expected, within the macrocycle series up to 6T ‐ PBI these cation species spectra undergo a broadening as well as a bathochromic shift to 840 nm and 1633 nm, respectively (Figure 5a). Further oxidation to the dicationic species 4T 2+ ‐ PBI (purple line) produces a strong absorption band at 953 nm (Figure 4d) which is shifted bathochromically for 5T 2+ ‐ PBI [16] (Figure 5b). The appearance of one single peak in the dicationic state for 4T 2+ ‐ PBI and 5T 2+ ‐ PBI indicates the formation of a bipolaron (spinless dication) species causing minimal structural distortion of the bridge [24] .…”

Section: Resultsmentioning

confidence: 99%

“…This fast tailored charge separation by concomitantly decelerated or impeded charge recombination could offer interesting prospects towards the understanding and general design of organic photovoltaic devices [15] . By exploiting the advances of macrocyclic π‐systems and imide linked PBI‐oligothiophene dyads research we envisioned to combine both fields (Figure 1) and enlarge the toolbox of a substance class introduced by our group in a recent report [16] …”

Section: Introductionmentioning

confidence: 99%

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Macrocyclic Donor‐Acceptor Dyads Composed of Oligothiophene Half‐Cycles and Perylene Bisimides

Bold

Stolte

Shoyama

et al. 2022

Chemistry A European J

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A series of donor‐acceptor (D−A) macrocyclic dyads consisting of an electron‐poor perylene bisimide (PBI) π‐scaffold bridged with electron‐rich α‐oligothiophenes bearing four, five, six and seven thiophene units between the two phenyl‐imide substituents has been synthesized and characterized by steady‐state UV/Vis absorption and fluorescence spectroscopy, cyclic and differential pulse voltammetry as well as transient absorption spectroscopy. Tying the oligothiophene strands in a conformationally fixed macrocyclic arrangement leads to a more rigid π‐scaffold with vibronic fine structure in the respective absorption spectra. Electrochemical analysis disclosed charged state properties in solution which are strongly dependent on the degree of rigidification within the individual macrocycle. Investigation of the excited state dynamics revealed an oligothiophene bridge size‐dependent fast charge transfer process for the macrocyclic dyads upon PBI subunit excitation.

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Section: Resultssupporting

confidence: 71%

“… Excerpt of the 1 H NMR spectra of 4T ‐ PBI , 5T ‐ PBI , [16] 6T ‐ PBI and 7T ‐ PBI (from bottom to top) in CD 2 Cl 2 at room temperature.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Macrocyclic Donor‐Acceptor Dyads Composed of Oligothiophene Half‐Cycles and Perylene Bisimides

Bold

Stolte

Shoyama

et al. 2022

Chemistry A European J

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Perylene‐Mediated Cytoskeletal Dysfunction Remodels Cancer‐Associated Fibroblasts to Augment Antitumor Immunotherapy

Shi,

Lou,

et al. 2024

Adv Healthcare Materials

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Targeted reprogramming cancer‐associated fibroblasts (CAFs) is one of the most essential cancer therapies. However, how to reprogram active CAFs towards deactivated state still remains immense challenges. To tackle this challenge, we herein prepared one perylene PDIC‐OC, which can trigger endogenous reactive oxygen species (ROS) burst to result in cytoskeletal dysfunction and cell apoptosis so that suppress transforming growth factor β (TGF‐β) production. As a result, PDIC‐OC can reprogram the activated CAFs and relieve immunosuppressive tumor microenvironment by efficient polarization of M2‐typed macrophages into M1‐typed ones, down‐regulation of alpha‐smooth muscle actin (α‐SMA), alleviation of hypoxic state to promote infiltration of cytotoxic T lymphocytes, and ultimately realized outstanding anti‐tumor performance on B16F10 tumor‐xenografted and lung‐metastatic mouse model even at low concentration of 1 mg kg−1 body weight. This work thus presents a novel strategy that cytoskeleton dysfunction and cell apoptosis cooperatively suppress the secretion of TGF‐β to reprogram CAFs and meanwhile clarifies intrinsic mechanism for perylene‐triggered chemo‐immunotherapy against hypoxic tumors.This article is protected by copyright. All rights reserved

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One‐Pot Synthesis and Excited‐State Dynamics of Null Exciton‐Coupled Diketopyrrolopyrroles Oligo‐Grids

Hou

Wan

et al. 2023

Advanced Materials

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Exciton coupling in molecular aggregates plays a vital role in impacting and fine‐tuning optoelectronic materials and their efficiencies in devices. A versatile platform to decipher aggregation‐property relationships is built around multichromophoric architectures. Here, a series of cyclic diketopyrrolopyrrole (DPP) oligomers featuring nanoscale gridarene structures and rigid bifluorenyl spacers are designed and synthesized via one‐pot Friedel–Crafts reaction. DPP dimer [2]Grid and trimer [3]Grid, which are cyclic rigid nanoarchitectures of rather different sizes, are further characterized via steady‐state and time‐resolved absorption and fluorescence spectroscopies. They exhibit monomer‐like spectroscopic signatures in the steady‐state measurements, from which null exciton couplings are derived. Moreover, in an apolar solvent, high fluorescence quantum yields and excited‐state dynamics that resembled DPP monomer are gathered. In a polar solvent, the localized singlet excited state on a single DPP dissociates into the adjacent null coupling DPP with charge transfer characteristics. This pathway facilitates the evolution of the symmetry‐broken charge‐separated state (SB‐CS). Notable is the fact that the SB‐CS of [2]Grid is, on one hand, in equilibrium with the singlet excited state and promotes, on the other hand, the formation of the triplet excited state with a yield of 32% via charge recombination.

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Macrocyclic Donor–Acceptor Dyads Composed of a Perylene Bisimide Dye Surrounded by Oligothiophene Bridges

Cited by 13 publications

References 73 publications

Macrocyclic Donor‐Acceptor Dyads Composed of Oligothiophene Half‐Cycles and Perylene Bisimides

Macrocyclic Donor‐Acceptor Dyads Composed of Oligothiophene Half‐Cycles and Perylene Bisimides

Perylene‐Mediated Cytoskeletal Dysfunction Remodels Cancer‐Associated Fibroblasts to Augment Antitumor Immunotherapy

One‐Pot Synthesis and Excited‐State Dynamics of Null Exciton‐Coupled Diketopyrrolopyrroles Oligo‐Grids

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