Hierarchical Assembly of a Phthalhydrazide‐Functionalized Helicene

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

doi:10.1002/ange.201007849

Cited by 190 publications

(26 citation statements)

References 46 publications

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“…[16] While helicenes have shown appearance in several supramolecular systems, they have never been used in the construction of coordination-driven cages. [17] We herein demonstrate that despite their highly twisted appearance, helicene-based bis-monodentate ligands can be used to assemble discrete [Pd 2 L 4 ] coordination cages exhibiting chirality-driven effects on their assembly and guest binding. We further report the first example of a homochiral interpenetrated [Pd 4 L 8 ] dimer, comprising eight interlocked helicenes.…”

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confidence: 90%

Chiral Self‐Discrimination and Guest Recognition in Helicene‐Based Coordination Cages

2019

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Chiral nanosized confinements play a major role for enantioselective recognition and reaction control in biological systems. Supramolecular self‐assembly gives access to artificial mimics with tunable sizes and properties. Herein, a new family of [Pd2L4] coordination cages based on a chiral [6]helicene backbone is introduced. A racemic mixture of the bis‐monodentate pyridyl ligand L1 selectively assembles with PdII cations under chiral self‐discrimination to an achiral meso cage, cis‐[Pd2L1P2L1M2]. Enantiopure L1 forms homochiral cages [Pd2L1P/M4]. A longer derivative L2 forms chiral cages [Pd2L2P/M4] with larger cavities, which bind optical isomers of chiral guests with different affinities. Owing to its distinct chiroptical properties, this cage can distinguish non‐chiral guests of different lengths, as they were found to squeeze or elongate the cavity under modulation of the helical pitch of the helicenes. The CD spectroscopic results were supported by ion mobility mass spectrometry.

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confidence: 90%

Chiral Self‐Discrimination and Guest Recognition in Helicene‐Based Coordination Cages

2019

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“…In contrast, the chiroptical properties of CPL emission at the excited state cannot be generated in straightforward ways. Intriguing attempts have been made to increase the degree of CPL emission by synthesizing p-conjugated polymers with chiral side chains, [45][46][47][48][49] chiral metal complexes, [50][51][52][53] and helicene derivatives with steric hindrance 54,55 On the other hand, CLC materials are readily available to efficiently generate CPL emission. When a fluorescent dye is dissolved in the CLC material, the selective reflection band superimposes on the broad fluorescence band emitted from the guest dye.…”

Section: Circular Polarization Of Laser Action From Clcsmentioning

confidence: 99%

Self-assembled organic and polymer photonic crystals for laser applications

Furumi

2012

Polym J

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This article describes an overview of recent developments in fabrication and uses of self-assembled photonic crystals (PCs) of organic and polymer materials, such as chiral liquid crystals (CLCs) and colloidal crystals (CCs), for laser applications. Both CLCs and CCs have intrinsic capabilities to spontaneously assemble 1D-PC and 3D-PC structures, respectively. When a periodic length in the PC structures of CLCs and CCs corresponds to several hundred nanometers of the light wavelength, the photonic band-gaps (PBGs) can be visualized as Bragg reflection colors. When combining fluorescence dyes in the CLCs and CCs, the stimulated laser action at PBG band edge(s) or within the PBG wavelength can be generated by optical excitation. Moreover, the optically excited laser action is controllable by external stimuli due to the self-organization of CLCs and CCs. This review highlights not only the research backgrounds of CLC and CC structures as PCs, but also the experimental results of their versatile soft and tunable laser applications. We believe that a wide variety of CLC and CC structures will have leading roles in the next generation of optoelectronic devices of organic and polymer materials.

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“…1,2 The application of CPL emission has been found in optical displays and memories, 3-6 chiroptical sensors, 7,8 and bioprobes. 11 Small chiral organic molecules, such as helicenes, [12][13][14][15][16][17][18] triphenylenes, 19 and paracyclophanes, 20 gave the |g lum | values in the range of 10 −3 to 10 −2 . Optical and electronic excitation of materials containing helically and axially arranged fluorophores produce strongly circularly polarized emission.…”

Section: Introductionmentioning

confidence: 99%

Circularly polarized luminescence of helically assembled pyrene π‐stacks on RNA and DNA duplexes

et al. 2018

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In this report, we describe the circularly polarized luminescence (CPL) of the RNA duplexes having one to four 2'-O-pyrene modified uridines (Upy) and the DNA duplexes having two, four, and six pyrene modified non-nucleosidic linkers (Py). Both the pyrene π-stack arrays formed on the RNA and DNA double helical structures exhibited pyrene excimer fluorescence. In the pyrene-modified RNA systems, the RNA duplex having four Upys gives CPL emission with g value of <0.01 at 480 nm. The structure of pyrene stacks on the RNA duplex may be rigidly regulated with increase in the Upy domains, which resulted in the CPL emission. In the DNA systems, the pyrene-modified duplexes containing two and four Pys exhibited CPL emission with g values of <0.001 at 505 nm. The pyrene π-stack arrays presented here show CPL emission. However, the g values are relatively small when compared with our previous system consisting of the pyrene-zipper arrays on RNA.

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Hierarchical Assembly of a Phthalhydrazide‐Functionalized Helicene

Cited by 190 publications

References 46 publications

Chiral Self‐Discrimination and Guest Recognition in Helicene‐Based Coordination Cages

Chiral Self‐Discrimination and Guest Recognition in Helicene‐Based Coordination Cages

Self-assembled organic and polymer photonic crystals for laser applications

Circularly polarized luminescence of helically assembled pyrene π‐stacks on RNA and DNA duplexes

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