Solvent‐ and Guest‐Responsive Self‐Assembly of Hamilton Receptor Tethered Bis(merocyanine) Dyes

Schmidt, Ralf; Uemura, Shinobu; Würthner, Frank

doi:10.1002/chem.201002159

Cited by 19 publications

(6 citation statements)

References 51 publications

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“…In a separate work, the same group designed a more sophisticated system based on a Hamilton receptor-tethered bis(MC) 68 that shows a biphasic solvent-induced self-assembly into two distinct species by a sequence of isodesmic and cooperative self-assembly events. 164 The aggregation was thoroughly investigated by means of UV/Vis in THF-MCH mixtures of various ratios (Fig. 20a).…”

Section: Dipole-dipole/zwitterionic Interactions and Other Contributionsmentioning

confidence: 99%

Strategies to create hierarchical self-assembled structures via cooperative non-covalent interactions

2015

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Cooperative phenomena are common processes involved in the hierarchical self-assembly of multiple systems in nature, such as the tobacco mosaic virus and a cell's cytoskeleton. Motivated by the high degree of order exhibited by these systems, a great deal of effort has been devoted in the past two decades to design hierarchical supramolecular polymers by combining different classes of cooperative interactions. In this review, we have classified the field of supramolecular polymers depending on the cooperative non-covalent forces driving their formation, with particular emphasis on recent examples from literature. We believe that this overview would help scientists in the field to design novel self-assembled systems with improved complexity and functionalities.

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Section: Dipole-dipole/zwitterionic Interactions and Other Contributionsmentioning

confidence: 99%

Strategies to create hierarchical self-assembled structures via cooperative non-covalent interactions

2015

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“…Schematic representation of the solvent- and guest-dependent self-assembly of Hamilton receptor tethered bis(merocyanine) dyes 14 . Reproduced with permission from ref . Copyright 2010 Wiley Publishers.…”

Section: Dynamic Behaviors Of Multiresponsive Supramolecular Complexesmentioning

confidence: 99%

“…For the construction of highly complicated supramolecular aggregates, Hamilton receptor tethered bis-(merocyanine) dye 14 that is responsive to solvent, concentration, and guest molecules was demonstrated to be a successful example to fabricate solvent-and guest-responsive supramolecular aggregates based on orthogonal hydrogen bonding and dipolar interactions. 40 As triggered by solvent polarity or concentration, different self-assembled species, such as oligomers, polymers, and inverted micelles, could be observed (Figure 12). Moreover, this system was also highly responsive toward the addition of guest molecules such as merocyanine, resulting in the transformation of the inverted micelles to more intricate supramolecular polymers.…”

Section: Dynamic Linear Supramolecular Polymersmentioning

confidence: 99%

Dynamic Supramolecular Complexes Constructed by Orthogonal Self-Assembly

et al. 2014

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CONSPECTUS: Supramolecular complexes, including various low-molecular-mass structures and large molecular aggregates that are assembled by reversible and highly directional noncovalent interactions, have attracted more and more attention due to their fascinating and unconventional chemical and physical properties that are different from those of traditional architectures encountered by covalently linked backbones. Supramolecular complexes are by nature dynamic architectures considering the reversibility of noncovalent interactions by which small molecular monomers can assemble into specific architectures that are able to be repeatably reorganized through the assembly/disassembly processes under certain environmental factors such as temperature, concentration, and solvent conditions. The construction of supramolecular complexes by orthogonal self-assembly with different types of highly specific, noninterfering interactions is currently attracting considerable interest since they not only can dynamically self-assemble, but also can be tuned by various external stimuli through addressing each type of noncovalent interaction separately. Therefore, these dynamic supramolecular complexes, especially with external responsiveness, represent the most outstanding candidates for the future development of functional and smart materials, and even mimic the assembling process of natural systems. In this Account, we will summarize the recent advances of dynamic supramolecular complexes constructed by orthogonal self-assembly in soluiton in two sections: (1) Construction strategies for supramolecular complexes based on orthogonal self-assembly, whose dynamic behaviors with external responsiveness were not experimentally investigated but potentially existed due to the intrinsic reversibility of noncovalent bonds; (2) dynamic behaviors of multiresponsive supramolecular complexes, which were experimentally reported to exhibit reversible multi-responsiveness to external stimuli. Dynamic nature is one of intrinsic properties of supramolecular complexes constructed by self-assembly. Therefore, in the first section, we will describe the dynamic self-assembly in the construction of supramolecular complexes, but will focus on their external responsive dynamic behaviors in the second section. In addition, considering that an increasing number of supramolecular complexes constructed by biological building blocks through bio-orthogonal assembly as mimics of biological systems have been reported in recent years, in the second section we will also present some typical examples on such special dynamic biological supramolecular complexes. The final part of this Account is devoted to foreseeing the rapid development of dynamic supramolecular complexes toward applications in functional and smart materials and fundamental questions facing dynamic supramolecular complexes in the future.

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“…Such a secondary amide group can act both as the H-bond acceptor and as the H-bond donor, which imparts new and useful properties to the molecule. Thus, Würthner and co-workers have designed various supramolecular systems-stable dimers [13], liquid crystals [14], and supramolecular 'polymers' [15]-all stabilized via H-bonds between a merocyanine molecule, which contains the barbituric acid residue, and a molecule bearing a Hamilton receptor [16] (see also reviews [17][18][19]). The resulting structures demonstrated pronounced nonlinear optical (NLO) and photorefractive (PR) properties as well as relatively high fluorescence quantum yields.…”

Section: Introductionmentioning

confidence: 99%

The unusual solvatochromism and solvatofluorochromism of longwave absorbing and emitting barbiturate merocyanine dyes

Ishchenko¹,

Kulinich²

2016

Methods Appl. Fluoresc.

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Spectral-fluorescent properties of a series of merocyanine dyes comprising the barbituric acid residue as the electron-accepting terminal group are investigated in comparison with those of their N,N-methylated analogues in media of various polarity. It is revealed that in polar aprotic solvents the electronic absorption spectra of the studied compounds are influenced dramatically by the formation of hydrogen bonds between the NH-groups of barbituric residue and solvent molecules. An effect of such nucleophilic solvation on the electronic structure of the studied dyes is analysed using both the spectral data obtained and the DFT/B3LYP quantum chemical simulation. It is found also, that solvation has comparatively weak influence on the shape and position of the fluorescence bands of the studied merocyanines while the fluorescence quantum yield changes substantially in solvents of various polarity.

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Solvent‐ and Guest‐Responsive Self‐Assembly of Hamilton Receptor Tethered Bis(merocyanine) Dyes

Cited by 19 publications

References 51 publications

Strategies to create hierarchical self-assembled structures via cooperative non-covalent interactions

Strategies to create hierarchical self-assembled structures via cooperative non-covalent interactions

Dynamic Supramolecular Complexes Constructed by Orthogonal Self-Assembly

The unusual solvatochromism and solvatofluorochromism of longwave absorbing and emitting barbiturate merocyanine dyes

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