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  • 1
    Online Resource
    Online Resource
    Highly Ordered Supramolecular Materials of Phase‐Separated Block Molecules for Long‐Range Exciton Transport
    Wiley ; 2023
    In:  Advanced Materials Vol. 35, No. 25 ( 2023-06)
    Details
    In: Advanced Materials, Wiley, Vol. 35, No. 25 ( 2023-06)
    Abstract: Efficient energy transport over long distances is essential for optoelectronic and light‐harvesting devices. Although self‐assembled nanofibers of organic molecules are shown to exhibit long exciton diffusion lengths, alignment of these nanofibers into films with large, organized domains with similar properties remains a challenge. Here, it is shown how the functionalization of C 3 ‐symmetric carbonyl‐bridged triarylamine trisamide (CBT) with oligodimethylsiloxane ( o DMS) side chains of discrete length leads to fully covered surfaces with aligned domains up to 125 × 70 µm 2 in which long‐range exciton transport takes place. The nanoscale morphology within the domains consists of highly ordered nanofibers with discrete intercolumnar spacings within a soft amorphous o DMS matrix. The o DMS prevents bundling of the CBT fibers, reducing the number of defects within the CBT columns. As a result, the columns have a high degree of coherence, leading to exciton diffusion lengths of a few hundred nanometers with exciton diffusivities (≈0.05 cm 2 s −1 ) that are comparable to those of a crystalline tetracene. These findings represent the next step toward fully covered surfaces of highly aligned nanofibers through functionalization with o DMS.
    Type of Medium: Online Resource
    ISSN: 0935-9648 , 1521-4095
    URL: Issue
    URL: Article
    DOI: 10.1002/adma.v35.25
    DOI: 10.1002/adma.202300891
    RVK:
    UA 1538
    Language: English
    Publisher: Wiley
    Publication Date: 2023
    detail.hit.zdb_id: 1474949-X
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  • 2
    Online Resource
    Online Resource
    Depolymerization of supramolecular polymers by a covalent reaction; transforming an intercalator into a sequestrator
    Royal Society of Chemistry (RSC) ; 2021
    In:  Chemical Science Vol. 12, No. 40 ( 2021), p. 13572-13579
    Details
    In: Chemical Science, Royal Society of Chemistry (RSC), Vol. 12, No. 40 ( 2021), p. 13572-13579
    Abstract: Controlling the reciprocity between chemical reactivity and supramolecular structure is a topic of great interest in the emergence of molecular complexity. In this work, we investigate the effect of a covalent reaction as a trigger to depolymerize a supramolecular assembly. We focus on the impact of an in situ thiol–ene reaction on the (co)polymerization of three derivatives of benzene-1,3,5-tricarboxamide (BTA) monomers functionalized with cysteine, hexylcysteine, and alkyl side chains: Cys-BTA, HexCys-BTA, and a-BTA. Long supramolecular polymers of Cys-BTA can be depolymerized into short dimeric aggregates of HexCys-BTA via the in situ thiol–ene reaction. Analysis of the system by time-resolved spectroscopy and light scattering unravels the fast dynamicity of the structures and the mechanism of depolymerization. Moreover, by intercalating the reactive Cys-BTA monomer into an unreactive inert polymer, the in situ thiol–ene reaction transforms the intercalator into a sequestrator and induces the depolymerization of the unreactive polymer. This work shows that the implementation of reactivity into supramolecular assemblies enables temporal control of depolymerization processes, which can bring us one step closer to understanding the interplay between non-covalent and covalent chemistry.
    Type of Medium: Online Resource
    ISSN: 2041-6520 , 2041-6539
    URL: Article
    DOI: 10.1039/D1SC04545H
    Language: English
    Publisher: Royal Society of Chemistry (RSC)
    Publication Date: 2021
    detail.hit.zdb_id: 2559110-1
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  • 3
    Online Resource
    Online Resource
    Controlling the Processability and Stability of Supramolecular Polymers Using the Interplay of Intra- and Intermolecular Interactions
    American Chemical Society (ACS) ; 2022
    In:  Macromolecules Vol. 55, No. 15 ( 2022-08-09), p. 6820-6829
    Details
    In: Macromolecules, American Chemical Society (ACS), Vol. 55, No. 15 ( 2022-08-09), p. 6820-6829
    Type of Medium: Online Resource
    ISSN: 0024-9297 , 1520-5835
    URL: Article
    DOI: 10.1021/acs.macromol.2c00976
    RVK:
    UA 5210
    Language: English
    Publisher: American Chemical Society (ACS)
    Publication Date: 2022
    detail.hit.zdb_id: 1491942-4
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  • 4
    Online Resource
    Online Resource
    Controlling the Length of Cooperative Supramolecular Polymers with Chain Cappers
    Wiley ; 2020
    In:  Chemistry – A European Journal Vol. 26, No. 44 ( 2020-08-06), p. 9964-9970
    Details
    In: Chemistry – A European Journal, Wiley, Vol. 26, No. 44 ( 2020-08-06), p. 9964-9970
    Abstract: The design and the characterization of supramolecular additives to control the chain length of benzene‐1,3,5‐tricarboxamide (BTA) cooperative supramolecular polymers under thermodynamic equilibrium is unraveled. These additives act as chain cappers of supramolecular polymers and feature one face as reactive as the BTA discotic to interact strongly with the polymer end, whereas the other face is nonreactive and therefore impedes further polymerization. Such a design requires fine tuning of the conformational preorganization of the amides and the steric hindrance of the motif. The chain cappers studied are monotopic derivatives of BTA, modified by partial N ‐methylation of the amides or by positioning of a bulky cyclotriveratrylene cage on one face of the BTA unit. This study not only clarifies the interplay between structural variations and supramolecular interactions, but it also highlights the necessity to combine orthogonal characterization methods, spectroscopy and light scattering, to elucidate the structures and compositions of supramolecular systems.
    Type of Medium: Online Resource
    ISSN: 0947-6539 , 1521-3765
    URL: Issue
    URL: Article
    DOI: 10.1002/chem.v26.44
    DOI: 10.1002/chem.202001293
    RVK:
    VA 1120 ; VA 3507
    Language: English
    Publisher: Wiley
    Publication Date: 2020
    detail.hit.zdb_id: 1478547-X
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  • 5
    Online Resource
    Online Resource
    Temperature Directs the Majority‐Rules Principle in Supramolecular Copolymers Driven by Triazine–Benzene Interactions
    Wiley ; 2023
    In:  Chemistry – A European Journal Vol. 29, No. 53 ( 2023-09-21)
    Details
    In: Chemistry – A European Journal, Wiley, Vol. 29, No. 53 ( 2023-09-21)
    Abstract: Supramolecular copolymers have typically been studied in the extreme cases, such as self‐sorting or highly mixed copolymer systems, while the intermediate systems have been less understood. We have reported the temperature‐dependent microstructure in copolymers of triazine‐ and benzene‐derivatives based on charge‐transfer interactions with a highly alternating microstructure at low temperatures. Here, we investigate the temperature‐dependent copolymerization further and increase the complexity by combining triazine‐ and benzene‐derivatives with opposite preferred helicities. In this case, intercalation of the benzene‐derivative into the triazine‐derivative assemblies causes a helical inversion. The inversion of the net helicity was rationalized by comparing the mismatch penalties of the individual monomers, which indicated that the benzene‐derivative dictates the helical screw‐sense of the supramolecular copolymers. Surprisingly, this was not reflected in further investigations of slightly modified triazine‐ and benzene‐derivatives, thus highlighting that the outcome is a subtle balance between structural features, where small differences can be amplified due to the competitive nature of the interactions. Overall, these findings suggest that the temperature‐dependent microstructure of triazine‐ and benzene‐based supramolecular copolymers determines the copolymer helicity of the presented system in a similar way as the mixed majority‐rules phenomenon.
    Type of Medium: Online Resource
    ISSN: 0947-6539 , 1521-3765
    URL: Issue
    URL: Article
    DOI: 10.1002/chem.v29.53
    DOI: 10.1002/chem.202301726
    RVK:
    VA 1120 ; VA 3507
    Language: English
    Publisher: Wiley
    Publication Date: 2023
    detail.hit.zdb_id: 1478547-X
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  • 6
    Online Resource
    Online Resource
    Photoswitchable Liquid‐to‐Solid Transition of Azobenzene‐Decorated Polysiloxanes
    Wiley ; 2023
    In:  Advanced Functional Materials Vol. 33, No. 36 ( 2023-09)
    Details
    In: Advanced Functional Materials, Wiley, Vol. 33, No. 36 ( 2023-09)
    Abstract: Having external control over fundamental properties of polymers, such as their physical state, is a crucial yet challenging design criterion for smart materials. Liquifying polymers through photochemical events has significantly advanced various research lines. However, the opposite process of solidifying a polymer that is intrinsically in a liquid state reversibly with light is unattained. Herein, the light‐controlled liquid‐to‐solid transition of polysiloxanes is reported, which are decorated with a small number of azobenzene‐functionalized ureidopyrimidinone (Azo‐UPy) pendants. The UPy moieties toggle between intra‐ and intermolecular hydrogen bonding via trans → cis photoisomerization of the azobenzene. This transformation on the molecular level leads to the formation of strong supramolecular cross‐links, which, in turn, results in the macroscopic solidification of the material. The photoswitching event enables the post‐synthetic tailoring of the polymers’ mechanical properties, thus providing an alternative to the addition of plasticizers or hardeners. Moreover, the adhesion strength of the photochromic material increases by a factor of 6 upon exposure to UV light. In situ illumination during rheological measurements reveals the delicate interplay between wavelength dependent penetration depth and photoswitching efficiency. This conceptually new (de)bonding on demand strategy paves the way for creating light‐responsive materials with exciting applications in temporal adhesion, recycling, lithography, and material processing.
    Type of Medium: Online Resource
    ISSN: 1616-301X , 1616-3028
    URL: Issue
    URL: Article
    DOI: 10.1002/adfm.v33.36
    DOI: 10.1002/adfm.202301246
    Language: English
    Publisher: Wiley
    Publication Date: 2023
    detail.hit.zdb_id: 2029061-5
    detail.hit.zdb_id: 2039420-2
    SSG: 11
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  • 7
    Online Resource
    Online Resource
    Circular depolarization spectroscopy: A new tool to study photo‐imprinting of chirality
    Wiley ; 2023
    In:  Chirality Vol. 35, No. 3 ( 2023-03), p. 147-154
    Details
    In: Chirality, Wiley, Vol. 35, No. 3 ( 2023-03), p. 147-154
    Abstract: When irradiating a molecular material containing photo‐isomerizable groups with pure circularly polarized light, a particular handedness may get imprinted into the material. To study the mechanism and kinetics of this process in situ and operando , we have developed a new chiroptical tool where the circular polarization of the incident circularly polarized light is monitored after transmission through the photoactive layer. Practical limits to the resolution and sensitivity of the measurements as well as its calibration are discussed. To aid interpretation of experimental results, we present kinetic Monte Carlo simulations on a model for the active material involving photo‐induced reorientation of molecules in a cholesteric organization. The simulations support the interpretation of a transient minimum in the degree of circular polarization of the transmitted light in terms of a nematic transient state during photo‐inversion of a cholesteric organization in the molecular material.
    Type of Medium: Online Resource
    ISSN: 0899-0042 , 1520-636X
    URL: Issue
    URL: Article
    DOI: 10.1002/chir.v35.3
    DOI: 10.1002/chir.23527
    Language: English
    Publisher: Wiley
    Publication Date: 2023
    detail.hit.zdb_id: 2001237-8
    SSG: 12
    SSG: 15,3
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  • 8
    Online Resource
    Online Resource
    Highly Ordered 2D‐Assemblies of Phase‐Segregated Block Molecules for Upconverted Linearly Polarized Emission
    Wiley ; 2020
    In:  Advanced Materials Vol. 32, No. 48 ( 2020-12)
    Details
    In: Advanced Materials, Wiley, Vol. 32, No. 48 ( 2020-12)
    Abstract: Materials based on the laminar ordering of self‐assembled molecules have a unique potential for applications requiring efficient energy migration through densely packed chromophores. Here, employing molecular assemblies of coil–rod–coil block molecules for triplet–triplet annihilation upconversion (TTA‐UC) based on triplet energy migration with linearly polarized emission is reported. By covalently attaching discrete‐length oligodimethylsiloxane ( o DMS) to 9,10‐diphenylanthracene (DPA), highly ordered 2D crystalline DPA sheets separated by o DMS layers are obtained. Transparent films of this material doped with small amounts of triplet sensitizer Pt II octaethylporphyrin show air‐stable TTA‐UC under non‐coherent excitation. Upon annealing, an increase in TTA‐UC up to two orders of magnitude is observed originating from both an improved molecular ordering of DPA and an increased dispersion of the sensitizer. The molecular alignment in millimeter‐sized domains leads to upconverted linearly polarized emission without alignment layers. By using a novel technique, upconversion imaging microscopy, the TTA‐UC intensity is spatially resolved on a micrometer scale to visually demonstrate the importance of molecular dispersion of sensitizer molecules for efficient TTA‐UC. The reported results are promising for anti‐counterfeiting and 3D night‐vision applications, but also exemplify the potential of discrete oligodimethylsiloxane functionalized chromophores for highly aligned and densely packed molecular materials.
    Type of Medium: Online Resource
    ISSN: 0935-9648 , 1521-4095
    URL: Issue
    URL: Article
    DOI: 10.1002/adma.v32.48
    DOI: 10.1002/adma.202004775
    RVK:
    UA 1538
    Language: English
    Publisher: Wiley
    Publication Date: 2020
    detail.hit.zdb_id: 1474949-X
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  • 9
    Online Resource
    Online Resource
    In situ Synthesis of Supramolecular Polymers: Finding the Right Conditions when Combining Covalent and Non‐Covalent Synthesis
    Wiley ; 2022
    In:  Angewandte Chemie Vol. 134, No. 34 ( 2022-08-22)
    Details
    In: Angewandte Chemie, Wiley, Vol. 134, No. 34 ( 2022-08-22)
    Abstract: The combination of covalent and non‐covalent synthesis is omnipresent in nature and potentially enables access to new materials. Yet, the fundamental principles that govern such a synthesis are barely understood. Here, we demonstrate how even simple reaction mixtures behave surprisingly complex when covalent reactions are coupled to self‐assembly processes. Specifically, we study the reaction behavior of a system in which the in situ formation of discotic benzene‐1,3,5‐tricarboxamide (BTA) monomers is linked to an intertwined non‐covalent reaction network including self‐assembly into helical BTA polymers. This system shows an unexpected phase‐separation behavior in which an interplay of reactant/product concentrations, side‐products and solvent purity determines the system composition. We envision that these insights can bring us one step closer to how to design the synthesis of systems in a combined covalent/non‐covalent fashion.
    Type of Medium: Online Resource
    ISSN: 0044-8249 , 1521-3757
    URL: Issue
    URL: Article
    DOI: 10.1002/ange.v134.34
    DOI: 10.1002/ange.202206729
    RVK:
    VA 2100
    RVK:
    VN 5020
    Language: English
    Publisher: Wiley
    Publication Date: 2022
    detail.hit.zdb_id: 505868-5
    detail.hit.zdb_id: 506609-8
    detail.hit.zdb_id: 514305-6
    detail.hit.zdb_id: 505872-7
    detail.hit.zdb_id: 1479266-7
    detail.hit.zdb_id: 505867-3
    detail.hit.zdb_id: 506259-7
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  • 10
    Online Resource
    Online Resource
    How Subtle Changes Can Make a Difference: Reproducibility in Complex Supramolecular Systems
    Wiley ; 2022
    In:  Angewandte Chemie International Edition Vol. 61, No. 41 ( 2022-10-10)
    Details
    In: Angewandte Chemie International Edition, Wiley, Vol. 61, No. 41 ( 2022-10-10)
    Abstract: The desire to construct complex molecular systems is driven by the need for technological (r)evolution and our intrinsic curiosity to comprehend the origin of life. Supramolecular chemists tackle this challenge by combining covalent and noncovalent reactions leading to multicomponent systems with emerging complexity. However, this synthetic strategy often coincides with difficult preparation protocols and a narrow window of suitable conditions. Here, we report on unsuspected observations of our group that highlight the impact of subtle “irregularities” on supramolecular systems. Based on the effects of pathway complexity, minute amounts of water in organic solvents or small impurities in the supramolecular building block, we discuss potential pitfalls in the study of complex systems. This article is intended to draw attention to often overlooked details and to initiate an open discussion on the importance of reporting experimental details to increase reproducibility in supramolecular chemistry.
    Type of Medium: Online Resource
    ISSN: 1433-7851 , 1521-3773
    URL: Issue
    URL: Article
    DOI: 10.1002/anie.v61.41
    DOI: 10.1002/anie.202206738
    RVK:
    VA 2100
    Language: English
    Publisher: Wiley
    Publication Date: 2022
    detail.hit.zdb_id: 2011836-3
    detail.hit.zdb_id: 123227-7
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