ssDNA Templated Self-Assembly of Chromophores

Janssen, Pim G. A.; Vandenbergh, Joke; Dongen, Joost L. J. van; Meijer, E. W.; Schenning, Albertus P. H. J.

doi:10.1021/ja0711967

Cited by 135 publications

(108 citation statements)

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“…11). [214][215][216] The templated selfassembly process has been characterized extensively, experimentally and theoretically, using UV-Vis, CD, 1 H NMR, and IR spectroscopy, molecular dynamics simulations, cryo-TEM, liquid AFM, electrospray ionization mass spectrometry, and light scattering. In these hybrid materials, the template controls the number of chromophores into uniform chiral supramolecular stacks, which are not accessible with the same precision via nontemplated supramolecular polymerization.…”

Section: Biomimetic Templated Polymerizationmentioning

confidence: 99%

Controlling supramolecular polymerization through multicomponent self‐assembly

Besenius

2016

J. Polym. Sci. Part A: Polym. Chem.

128

102

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The self-assembly into supramolecular polymers is a process driven by reversible non-covalent interactions between monomers, and gives access to materials applications incorporating mechanical, biological, optical or electronic functionalities. Compared to the achievements in precision polymer synthesis via living and controlled covalent polymerization processes, supramolecular chemists have only just learned how to developed strategies that allow similar control over polymer length, (co)monomer sequence and morphology (random, alternating or blocked ordering). This highlight article discusses the unique opportunities that arise when coassembling multicomponent supramolecular polymers, and focusses on four strategies in order to control the polymer architecture, size, stability and its stimuli-responsive properties: (1) endcapping of supramolecular polymers, (2) biomimetic templated polymerization, (3) controlled selectivity and reactivity in supramolecular copolymerization, and (4) living supramolecular polymerization. In contrast to the traditional focus on equilibrium systems, our emphasis is also on the manipulation of selfassembly kinetics of synthetic supramolecular systems. V C 2016

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Section: Biomimetic Templated Polymerizationmentioning

confidence: 99%

Controlling supramolecular polymerization through multicomponent self‐assembly

Besenius

2016

J. Polym. Sci. Part A: Polym. Chem.

128

102

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“…In that context the development of discotic monomers has proven to be a valuable route to allow for the synthesis of rod-like supramolecular polymers (19), whose potential applications in functional soft matter include electronics, biomedical engineering, and sensors (20)(21)(22)(23)(24)(25)(26). Considering the enormous interest in such systems, it is surprising that efforts to control the size and shape of nano-and micrometer size one-dimensional objects are rare (27)(28)(29); successful strategies rely on the use of templates (30,31), end cappers (32), or selective solvent techniques (33).…”

mentioning

confidence: 99%

Controlling the growth and shape of chiral supramolecular polymers in water

Besenius

Portale²,

Bomans

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

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A challenging target in the noncovalent synthesis of nanostructured functional materials is the formation of uniform features that exhibit well-defined properties, e.g., precise control over the aggregate shape, size, and stability. In particular, for aqueousbased one-dimensional supramolecular polymers, this is a daunting task. Here we disclose a strategy based on self-assembling discotic amphiphiles that leads to the control over stack length and shape of ordered, chiral columnar aggregates. By balancing out attractive noncovalent forces within the hydrophobic core of the polymerizing building blocks with electrostatic repulsive interactions on the hydrophilic rim we managed to switch from elongated, rod-like assemblies to small and discrete objects. Intriguingly this rod-tosphere transition is expressed in a loss of cooperativity in the temperature-dependent self-assembly mechanism. The aggregates were characterized using circular dichroism, UV and 1H-NMR spectroscopy, small angle X-ray scattering, and cryotransmission electron microscopy. In analogy to many systems found in biology, mechanistic details of the self-assembly pathways emphasize the importance of cooperativity as a key feature that dictates the physical properties of the produced supramolecular polymers.aqueous self-assembly | controlled architecture | supramolecular polymerization | dynamic materials M olecular self-assembly has emerged as a fascinating area in its own right (1, 2). A toolbox initially developed by supramolecular chemists quickly expanded into an interdisciplinary field aiming at the manipulation of matter at the molecular scale (3, 4). Up until recently self-assembly in dilute aqueous environments has predominantly dealt with linear amphiphiles that form closed structures (5-9), such as spherical micelles, cylindrical or rod-like micelles, and vesicles using, for example, phospholipids (10, 11), synthetic block copolymers (12, 13), or dendrimers (14). Morphological control in objects of defined size or shape, and transitions between different morphologies are increasingly well understood (15)(16)(17)(18). Surprisingly, however, the generality of these concepts has not been translocated into another area of increasing interest, namely, the self-assembly of one-dimensional arrays. In that context the development of discotic monomers has proven to be a valuable route to allow for the synthesis of rod-like supramolecular polymers (19), whose potential applications in functional soft matter include electronics, biomedical engineering, and sensors (20)(21)(22)(23)(24)(25)(26). Considering the enormous interest in such systems, it is surprising that efforts to control the size and shape of nano-and micrometer size one-dimensional objects are rare (27-29); successful strategies rely on the use of templates (30, 31), end cappers (32), or selective solvent techniques (33).In order to control the growth of aqueous one-dimensional supramolecular polymers, we propose to utilize electrostatic repulsive contributions in analogy to surfactant...

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“…Besides base modification [14] or the incorporation of p-conjugated oligomers into the DNA backbone by covalent linking, [15][16][17] the use of the H-bonding recognition process in the design of (single-strand) oligonucleotide-chromophore conjugates also appears as an interesting path to prepare monodisperse aggregates. [18,19] This approach offers a major advantage: by exploiting the base recognition process, it would be possible to control the sequence of different functional units along the single-strand DNA (ssDNA). This templating approach based on H-bonding has been exploited by Iwaura et al to organize thymine-capped (bola)amphiphiles, for example, a water-soluble p-conjugated oligo( p-phenylene vinylene) derivative that binds between two strands of oligoadenine.…”

mentioning

confidence: 99%

“…The self-assembly leads to right-handed helical hybrid structures, as indicated by circular-dichroism (CD) spectroscopy. [19] Although the spectroscopic data indicate the presence of fully-bound complexes (one guest for each thymine of the ssDNA), detailed information on the influence of the molecular structure of the guest on the structural order and intermolecular interactions in those systems is lacking. In this communication, we report on the supramolecular organization in these hybrid assemblies composed of a oligothymine template (dT n ) with a naphthalene or an oligo( p-phenylene vinylene) derivative equipped with a diaminotriazine unit (NT or OPV, respectively, see Scheme 1).…”

mentioning

confidence: 99%

Supramolecular Organization of ssDNA‐Templated π‐Conjugated Oligomers via Hydrogen Bonding

et al. 2009

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The templated self‐assembly of water‐soluble π‐conjugated molecules bearing a diaminotriazine moiety H‐bonding to a single‐strand oligothymine template leads to defined structures. We study these assemblies with molecular modeling, circular dichroism spectroscopy, and scanning probe microscopy, to get a better understanding of the factors governing the supramolecular organization and structural order.

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ssDNA Templated Self-Assembly of Chromophores

Cited by 135 publications

References 13 publications

Controlling supramolecular polymerization through multicomponent self‐assembly

Controlling supramolecular polymerization through multicomponent self‐assembly

Controlling the growth and shape of chiral supramolecular polymers in water

Supramolecular Organization of ssDNA‐Templated π‐Conjugated Oligomers via Hydrogen Bonding

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