3D supramolecular self-assembly of [60]fullerene hexaadducts decorated with triarylamine molecules

Gavat, Odile; Trinh, Thi Minh Nguyet; Moulin, Émilie; Ellis, Thomas; Maaloum, Mounir; Fleith, Guillaume; Nierengarten, Jean‐François; Giuseppone, Nicolas

doi:10.1039/c8cc04079f

Cited by 9 publications

(6 citation statements)

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“…Obviously concentration and temperature also play an important role as is the case for any supramolecular self-assembly. Interestingly, TAA derivatives were shown to produce columnar stacks even when bearing very large substituents in solution, − in thin films, , or in the bulk with the formation of various liquid-crystalline mesophases (Figure F). , Strikingly, even when TAA are conjugated to substituents as large as fullerene moieties, 1D or 3D supramolecular polymers can be obtained (Figure G). , …”

Section: Structural Aspects Of Triarylamine-based Supramolecular Poly...mentioning

confidence: 99%

Triarylamine-Based Supramolecular Polymers: Structures, Dynamics, and Functions

2019

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Triarylamine molecules and triarylamine-based covalent polymers have been extensively investigated for more than sixty years in academics and industry because of their intriguing electronic and optical characteristics. However, despite the profusion of studies made on these derivatives, only very recently have the first examples of supramolecular polymers based on the triarylamine motif been described in the literature. Specifically, our research group has shown that, by adding supplementary hydrogen bonding moieties such as amide functions in their periphery, it becomes possible to tightly pack triarylamine molecules in columnar supramolecular stacks presenting a collinear arrangement of their central nitrogen atoms. These supramolecular polymers can self-assemble into various soft hierarchical structures such as helical fibers, nanorods, nanospheres, and nanoribbons in the sol and in the gel states, into liquid-crystalline mesophases, as well as into highly organized supramolecular frameworks and their single crystals thereof.Interestingly, the associated supramolecular polymerization mechanism involves a nucleation step MAIN TEXT

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Section: Structural Aspects Of Triarylamine-based Supramolecular Poly...mentioning

confidence: 99%

Triarylamine-Based Supramolecular Polymers: Structures, Dynamics, and Functions

2019

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“…[15] Multi-branched three-dimensional hole-transporting materials (HTMs) have been also prepared by grafting extended triarylamine (TAA) residues onto a fullerene hexaadduct core. [16][17] These compounds showed interesting features as HTMs in perovskite solar cells (PSCs). [16] In addition to high photochemical stability, an increased number of peripheral TAA units appeared beneficial to the performances of the photocells.…”

Section: Introductionmentioning

confidence: 99%

“…For example, fullerene hexa‐adducts decorated with boron‐dipyrromethene (bodipy) dyes have been used as solar energy concentrators to improve the light‐to‐electricity conversion of amorphous silicon photocells [15] . Multi‐branched three‐dimensional hole‐transporting materials (HTMs) have been also prepared by grafting extended triarylamine (TAA) residues onto a fullerene hexa‐adduct core [16–17] . These compounds showed interesting features as HTMs in perovskite solar cells (PSCs) [16] .…”

Section: Introductionmentioning

confidence: 99%

Dendritic‐Like Molecules Built on a Pillar[5]arene Core as Hole Transporting Materials for Perovskite Solar Cells

Bettucci

Pascual

Turren‐Cruz

et al. 2021

Chemistry A European J

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Multi-branched molecules have recently demonstrated interesting behaviour as charge-transporting materials within the fields of perovskite solar cells (PSCs). For this reason, extended triarylamine dendrons have been grafted onto a pillar [5]arene core to generate dendrimer-like compounds, which have been used as hole-transporting materials (HTMs) for PSCs. The performances of the solar cells containing these novel compounds have been extensively investigated. Interestingly, a positive dendritic effect has been evidenced as the hole transporting properties are improved when going from the first to the second-generation compound. The stability of the devices based on the best performing pillar[5]arene material has been also evaluated in a high-throughput ageing setup for 500 h at high temperature. When compared to reference devices prepared from spiro-OMeTAD, the behaviour is similar. An analysis of the economic advantages arising from the use of the pillar[5] arene-based material revealed however that our pillar [5] arene-based material is cheaper than the reference.

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“…Out of these methods, the liquid-liquid interfacial precipitation (LLIP) method initiated by Miyazawa [29] enables a range of dimensionally-controlled nanostructures, such as one-dimensional (1D) nanotubes, two dimensional (2D) [30,31], three dimensional (3D) cubes [18], and nanospheres [32]. Such diversity of nanostructures exhibits enhanced supramolecular properties [33,34]. The solvated 3D fullerene cube can grow into a hierarchical structure with mesoporous nanorods on its cube surface upon being washed by isopropanol alcohol [18], whose vapor-phase sensing performance has been promoted after structural rearrangement.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembled Corn-Husk-Shaped Fullerene Crystals as Excellent Acid Vapor Sensors

Wei

Song

et al. 2022

Chemosensors

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Low-molecular-weight acid vapors cause aging and destruction in material processing. In this paper, facile fabrication of novel corn-husk-shaped fullerene C60 crystals (CHFCs) through the dynamic liquid–liquid interfacial precipitation method is reported. The CHFCs were grown at the liquid–liquid interface between isopropyl alcohol (IPA) and a saturated solution of C60 in mesitylene under ambient temperature and pressure conditions. The average length, outer diameter, and inner diameter of CHFCs were ca. 2.88 μm, 672 nm, and 473 nm, respectively. X-ray diffraction (XRD) analysis showed the CHFCs exhibit a mixed face-centered cubic (fcc) and hexagonal-close pack (hcp) crystal phases with lattice parameters a = 1.425 nm, V = 2.899 nm3 for fcc phase and a = 2.182 nm, c = 0.936 nm, a/c ratio = 2.33, and V = 3.859 nm3 for hcp phase. The CHFCs possess mesoporous structure as confirmed by transmission electron microscopy (TEM) and nitrogen sorption analysis. The specific surface area and the pore volume were ca. 57.3 m2 g−1 and 0.149 cm3 g−1, respectively, are higher than the nonporous pristine fullerene C60. Quartz crystal microbalance (QCM) sensing results show the excellent sensing performance CHFCs sensitive to acetic acid vapors due to the enhanced diffusion via mesoporous architecture and hollow structure of the CHFCs, demonstrating the potential of the material for the development of a new sensor system for aliphatic acid vapors sensing.

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3D supramolecular self-assembly of [60]fullerene hexaadducts decorated with triarylamine molecules

Cited by 9 publications

References 50 publications

Triarylamine-Based Supramolecular Polymers: Structures, Dynamics, and Functions

Triarylamine-Based Supramolecular Polymers: Structures, Dynamics, and Functions

Dendritic‐Like Molecules Built on a Pillar[5]arene Core as Hole Transporting Materials for Perovskite Solar Cells

Self-Assembled Corn-Husk-Shaped Fullerene Crystals as Excellent Acid Vapor Sensors

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