Hierarchical Assembly of a Phthalhydrazide‐Functionalized Helicene

Kaseyama, Takahiro; Furumi, Seiichi; Zhang, Xuan; Tanaka, Ken; Takeuchi, Masayuki

doi:10.1002/anie.201007849

Cited by 224 publications

(80 citation statements)

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“…The additional introduction of a hydrogenbonding interactions, which are substantially stronger than pp interactions, may increase the introduction of the other enantiomers, which can often results in the morphological change of aggregated structures as exemplified in many cases. [9,12] In conclusion, we have demonstrated the control of the length of supramolecular polymers as well as chiroptical properties of a bichromophoric binaphthalene derivative by varying the ee value. The key features of the present system for successfully controlling the length of the supramolecular polymers include the following points: a) The homochiral binding favors the fibrous growth whereas the heterochiral association leads to the nonfibrous assembly, and both events take place under isodesmic conditions, which are simply controlled by K homo and K hetero , respectively; b) The binding constant for the nonfibrous assembly should be larger than that for the fibrous assembly; c) The absence of the hydrogenbonding interaction emphasizes the effects of the geometry of the twisting bichromophoric p-core in self-assembling processes, thus leading to an efficient self-sorting behavior.…”

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confidence: 76%

Self‐Discriminating Termination of Chiral Supramolecular Polymerization: Tuning the Length of Nanofibers

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confidence: 76%

Self‐Discriminating Termination of Chiral Supramolecular Polymerization: Tuning the Length of Nanofibers

et al. 2015

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“…Herein, we utilize enantiomeric mixing for controlling the length as well as the supramolecular chirality of supramolecular polymers. Similar behavior was earlier observed in the self-assemblies driven by p-p stacking interactions of core-twisted p-systems including helicene derivatives [12] and bay-substituted PBIs. After annealing, the fibrous assemblies completely disappeared and ill-structured nanoparticles with ad iameter of 10-20 nm were formed ( Figure 1B).…”

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confidence: 86%

Self‐Discriminating Termination of Chiral Supramolecular Polymerization: Tuning the Length of Nanofibers

et al. 2015

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Directing the supramolecular polymerization towards ap referred type of organization is extremely important in the design of functional soft materials.Proposed herein is asimple methodology to tune the length and optical chirality of supramolecular polymers formed from ac hiral bichromophoric binaphthalene by the control of enantiomeric excess (ee). The enantiopure compound gave thin fibers longer than afew microns,while the racemic mixture favored the formation of nanoparticles.T he thermodynamic study unveils that the heterochiral assembly gets preference over the homochiral assembly.T he stronger heterochiral binding over homochiral one terminated the elongation of fibrous assembly,thus leading to ac ontrol over the length of fibers in the nonracemic mixtures.T he supramolecular polymerization driven by p-p interactions highlights the effect of the geometry of atwisted pcore on this self-sorting assembly.The past two decades have witnessed increased attention in the field of the self-assembly of small molecules into complex architectures. [1] This interest in supramolecular polymers formed by noncovalent interactions arises mainly because of a) the desire to mimic life systems so as to understand the process of self-assembly in biological macromolecules [2a] and b) the ability to build nanostructures for practical applications by utilizing ab ottom-up approach. [2b-d] Theb ottom-up approach drives the formation of supramolecular aggregates through acombined effect of different noncovalent intermolecular forces,thus leading to complex superstructures,often possessing af ibrous nature. [3] Molecules possessing chiral centers act as building blocks for the fabrication of helical nanostructures,wherein the supramolecular chirality is determined by the chirality at the molecular level. [4,5] The fascinating structural features of different chiral nanostructures,s uch as helices,n anotapes,a nd nanotubes have attracted great interest because of their resemblance to biological structures [6a] and possible applications in chiral sensing and catalysis. [6b-d] Thep erformance of functional organic materials in optoelectronic devices is largely dependent on the organization of molecular components. [6] Hence,d irecting the selfassembly towards ap referred type of organization is an extremely important step in the design of such materials. Recently,w er eported the self-assembly of chiral binaphthalenes,b earing two perylene bis(imide) (PBI) units (1; Scheme 1), [7] into dissimilar morphologies depending on the solvent system. [8] They formed helical fibers through p-p stacking interactions in methylcyclohexane (MCH), but formed spherical aggregates in chloroform at high concentration. [8] Thef ibrous assemblies gave superior chiroptical properties,including circularly polarized luminescence (CPL) relative to the spherical aggregates.I nt he present work, we introduce an ew methodology to control the length of the fibers through the mixing of enantiomers possessing the opposite chirality.I nt his regard, earlier i...

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“…The CPL properties of (M)-10 were observed in CHCl 3 and methanol, wherein (M)-10 forms monomers by disruption of hydrogen-bonding interactions. The g lum values were -3.5 × 10 -2 at 476 nm in CHCl 3 (4 × 10 -4 M) and -2.1 × 10 -2 in methanol [14].…”

Section: Stimuli-responsive Cpl Properties Of -Conjugated Moleculesmentioning

confidence: 93%

“…Takeuchi et al prepared phthalhydrazide-functionalized helicene (M)-10 ( Fig. 8a), which formed trimeric disks by hydro-H. MAEDA AND Y. BANDO gen-bonding interactions in nonpolar solvents such as CHCl 3 [14]. The CPL properties of (M)-10 were observed in CHCl 3 and methanol, wherein (M)-10 forms monomers by disruption of hydrogen-bonding interactions.…”

Section: Stimuli-responsive Cpl Properties Of -Conjugated Moleculesmentioning

confidence: 99%

Recent progress in research on stimuli-responsive circularly polarized luminescence based on π-conjugated molecules

Maeda

Bando

2013

Pure and Applied Chemistry

141

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This short review article summarizes recent progress in research on various stimuli-responsive circularly polarized luminescence (CPL) properties derived from π-conjugated molecules and related materials. As representative examples, assembled structures of chiral π-conjugated polymers and molecules showed tunable CPL resulting from the enhancement of chirality induction by aggregation. Fascinating CPL-active species, pyrrole-based anionresponsive π-conjugated molecules exhibiting CPL induced by anion binding and ion pairing, are also discussed.

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Hierarchical Assembly of a Phthalhydrazide‐Functionalized Helicene

Cited by 224 publications

References 46 publications

Self‐Discriminating Termination of Chiral Supramolecular Polymerization: Tuning the Length of Nanofibers

Self‐Discriminating Termination of Chiral Supramolecular Polymerization: Tuning the Length of Nanofibers

Self‐Discriminating Termination of Chiral Supramolecular Polymerization: Tuning the Length of Nanofibers

Recent progress in research on stimuli-responsive circularly polarized luminescence based on π-conjugated molecules

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Hierarchical Assembly of a Phthalhydrazide‐Functionalized Helicene

Cited by 224 publications

References 46 publications

Self‐Discriminating Termination of Chiral Supramolecular Polymerization: Tuning the Length of Nanofibers

Self‐Discriminating Termination of Chiral Supramolecular Polymerization: Tuning the Length of Nanofibers

Self‐Discriminating Termination of Chiral Supramolecular Polymerization: Tuning the Length of Nanofibers

Recent progress in research on stimuli-responsive circularly polarized luminescence based on &pi;-conjugated molecules

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Recent progress in research on stimuli-responsive circularly polarized luminescence based on π-conjugated molecules