π-Stacked Polymer Consisting of a Pseudo–meta–[2.2]Paracyclophane Skeleton

Maeda, Hazuki; Kameda, Mayu; Hatakeyama, Takuji; Morisaki, Yasuhiro

doi:10.3390/polym10101140

Cited by 9 publications

(5 citation statements)

References 27 publications

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“…As a consequence of metal coordination, the helical structure of double helicate is mainly governed by the configuration of organic strands at the metal centers. [2.2]Paracyclophane (PCP), which displays diverse planar chiral structures due to its pseudo- para , meta and ortho orientations, has been widely utilized as chiral auxiliaries and ligands 69 – 71 for diverse applications from asymmetric synthesis to supramolecular assembly 72 , polymer chemistry 73 and material science 74 . Recently, Chujo and coworkers constructed one-handed double helices based on planar chiral PCP 75 , 76 .…”

Section: Introductionmentioning

confidence: 99%

[2,2] Paracyclophanes-based double helicates for constructing artificial light-harvesting systems and white LED device

Lian

Liu

et al. 2023

Nat Commun

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The construction of efficient artificial light-harvesting systems (ALHSs) is of vital importance in utilizing solar energy. Herein, we report the non-covalent syntheses of double helicates PCP-TPy1/2 and Rp,Rp-PCP-TPy1/2 by metal-coordination interaction and their applications in ALHSs and white light-emitting diode (LED) device. All double helicates exhibit significant aggregation-induced emission in tetrahydrofuran/water (1:9, v/v) solvent. The aggregated double helicates can be used to construct one-step or sequential ALHSs with fluorescent dyes Eosin Y (EsY) and Nile red (NiR) with the energy transfer efficiency up to 89.3%. Impressively, the PMMA film of PCP-TPy1 shows white-light emission when doped 0.075% NiR, the solid of double helicates (Rp,Rp-) PCP-TPy2 can be used as the additive of a blue LED bulb to achieve white-light emission. In this work, we provided a general method for the preparation of novel double helicates and explored their applications in ALHSs and fluorescent materials, which will promote future construction and application of helicates as emissive devices.

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Section: Introductionmentioning

confidence: 99%

[2,2] Paracyclophanes-based double helicates for constructing artificial light-harvesting systems and white LED device

Lian

Liu

et al. 2023

Nat Commun

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“…Metallocene-based linkers are frequently employed to manufacture novel structures; − however, this scaffold cannot be further extended to afford multifarious multitopic linkers, significantly limiting their development for both structures and properties. To circumvent this issue, we can alternatively use a [2.2]paracyclophane (PCP) scaffold, which has an aromatic cyclophane compound with two benzene rings fixed at the para -positions by two ethylene chains. − This rigid π-stacked system, which is similar to a metallocene complex, is capable of undergoing multiple synthetic transformations, which has led to a new wave of research interest in constructing functional materials. − However, the employment of such scaffold into crystalline MOF materials has rarely been explored. , …”

Section: Introductionmentioning

confidence: 99%

Water Sorption Evolution Enabled by Reticular Construction of Zirconium Metal–Organic Frameworks Based on a Unique [2.2]Paracyclophane Scaffold

et al. 2022

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Water vapor sorption by metal–organic frameworks (MOFs) has gathered significant interest because of its prominent potential in many applications such as moisture harvesting, dehumidification, heat pump regulation, and hydrolysis catalysis. However, the reticular design and exploration of robust and high-performing Zr-MOFs for such purposes remains a sought-after endeavor. In this work, we present the deployment of reticular chemistry to target a series of robust Zr-MOFs based on a unique [2.2]paracyclophane (PCP) scaffold. The ease of functionalization of PCP enables the desired synthesis of three carboxylate linkers, one ditopic and two tetratopic, which further assemble into a total of five Zr-MOFs with distinct topological structures, i.e., a new 2D net (NU-700), fcu (NU-405), flu (NU-1800), she (NU-602), scu (NU-913). Notably, the water vapor sorption performances of all the Zr-MOFs are highly dependent on their framework topology and pore metric, in which NU-602 and NU-913 with uniform 1D channels exhibit S-shaped water sorption isotherms with a steep pore-filling step and high uptake capacities of 0.72 g g–1 at 70% relative humidity (RH) and 0.88 g g–1 at 60% RH, respectively. Moreover, NU-913 displays exceptionally high working capacity of 0.72 g g–1 in the range of 40–60% RH. Additionally, we demonstrate that the hydrolytic stability and water adsorption-desorption recyclability of NU-913 can be remarkably improved by capping the Zr6 nodes with the more hydrophobic agent, trifluoroacetic acid, making it a potential candidate for water sorption-based applications.

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“…This approach has been used by Morisaki and Chujo et al ., who have been very active in the field of optically active chiral [2.2]paracyclophanes in recent years, successfully designing conjugated microporous polymers, dendrimers and 3D propeller‐like structures with exceptionally high | g lum |=1.1×10 −2 . [ 22 , 23 , 24 , 25 , 26 ] Others have developed PCP‐based compounds capable of thermally activated delayed fluorescence or solvent‐induced switching of the CPL sign. [ 27 , 28 ]…”

Section: Introductionmentioning

confidence: 99%

“…By extension of the π‐system of the [2.2]PCP and introduction of chromophore substituents their absorption and emission properties should be significantly altered and potentially improved for (chir‐)optical applications. This approach has been used by Morisaki and Chujo et al ., who have been very active in the field of optically active chiral [2.2]paracyclophanes in recent years, successfully designing conjugated microporous polymers, dendrimers and 3D propeller‐like structures with exceptionally high | g lum |=1.1×10 −2 [22–26] . Others have developed PCP‐based compounds capable of thermally activated delayed fluorescence or solvent‐induced switching of the CPL sign [27,28] …”

Section: Introductionmentioning

confidence: 99%

“…This approach has been used by Morisaki and Chujo et al, who have been very active in the field of optically active chiral [2.2]paracyclophanes in recent years, successfully designing conjugated microporous polymers, dendrimers and 3D propeller-like structures with exceptionally high j g lum j = 1.1 × 10 À 2 . [22][23][24][25][26] Others have developed PCP-based compounds capable of thermally activated delayed fluorescence or solvent-induced switching of the CPL sign. [27,28] Formal substitution of polycyclic aromatic hydrocarbons (PAHs) with boron-nitrogen (BN) units that are isoelectronic to a CC pair is a common way in organic materials science to modify the electronic properties of a compound without altering its structure.…”

Section: Introductionmentioning

confidence: 99%

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Bright Luminescence by Combining Chiral [2.2]Paracyclophane with a Boron–Nitrogen‐Doped Polyaromatic Hydrocarbon Building Block

Rapp

Leis

Zinna

et al. 2022

Chemistry A European J

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Novel BN‐doped compounds based on chiral, tetrasubstituted [2.2]paracyclophane and NBN‐benzo[f,g]tetracene were synthesized by Sonogashira–Hagihara coupling. Conjugated ethynyl linkers allow electronic communication between the π‐electron systems through‐bond, whereas through‐space interactions are provided by strong π–π overlap between the pairs of NBN‐building blocks. Excellent optical and chiroptical properties in racemic and enantiopure conditions were measured, with molar absorption coefficients up to ϵ=2.04×105 M−1 cm−1, fluorescence quantum yields up to ΦPL=0.70, and intense, mirror‐image electronic circular dichroism and circularly polarized luminescence signals of the magnitude of 10−3 for the absorption and luminescence dissymmetry factors. Computed glum,calcd. values match the experimental ones. Electroanalytical data show both oxidation and reduction of the ethynyl‐linked tetra‐NBN‐substituted paracyclophane, with an overlap of two redox processes for oxidation leading to a diradical dication.

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π-Stacked Polymer Consisting of a Pseudo–meta–[2.2]Paracyclophane Skeleton

Cited by 9 publications

References 27 publications

[2,2] Paracyclophanes-based double helicates for constructing artificial light-harvesting systems and white LED device

[2,2] Paracyclophanes-based double helicates for constructing artificial light-harvesting systems and white LED device

Water Sorption Evolution Enabled by Reticular Construction of Zirconium Metal–Organic Frameworks Based on a Unique [2.2]Paracyclophane Scaffold

Bright Luminescence by Combining Chiral [2.2]Paracyclophane with a Boron–Nitrogen‐Doped Polyaromatic Hydrocarbon Building Block

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