A Family of Supramolecular Frameworks of Polyconjugated Molecules Hosted in Aromatic Nanochannels

Sozzani, P; Comotti, Angiolina; Bracco, Silvia; Simonutti, Roberto

doi:10.1002/ange.200353479

Cited by 24 publications

(11 citation statements)

References 45 publications

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“…However, controlled large-scale assembly is one of the more crucial aspects for effective charge transport in organic semiconductors and is difficult to achieve. The emergence of organic frameworks (OFs) has opened an avenue for predicting and controlling the molecular assembly, especially in covalent OFs (COFs) (14)(15)(16)(17). The final COF topology can now be determined based on the relative geometries of raw materials.…”

mentioning

confidence: 99%

Noncovalent π-stacked robust topological organic framework

Meng

Yang

Xiao

et al. 2020

Proc. Natl. Acad. Sci. U.S.A.

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Organic frameworks (OFs) offer a novel strategy for assembling organic semiconductors into robust networks that facilitate transport, especially the covalent organic frameworks (COFs). However, poor electrical conductivity through covalent bonds and insolubility of COFs limit their practical applications in organic electronics. It is known that the two-dimensional intralayer π∙∙∙π transfer dominates transport in organic semiconductors. However, because of extremely labile inherent features of noncovalent π∙∙∙π interaction, direct construction of robust frameworks via noncovalent π∙∙∙π interaction is a difficult task. Toward this goal, we report a robust noncovalent π∙∙∙π interaction-stacked organic framework, namely πOF, consisting of a permanent three-dimensional porous structure that is held together by pure intralayer noncovalent π∙∙∙π interactions. The elaborate porous structure, with a 1.69-nm supramaximal micropore, is composed of fully conjugated rigid aromatic tetragonal-disphenoid-shaped molecules with four identical platforms. πOF shows excellent thermostability and high recyclability and exhibits self-healing properties by which the parent porosity is recovered upon solvent annealing at room temperature. Taking advantage of the long-range π∙∙∙π interaction, we demonstrate remarkable transport properties of πOF in an organic-field-effect transistor, and the mobility displays relative superiority over the traditional COFs. These promising results position πOF in a direction toward porous and yet conductive materials for high-performance organic electronics.

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confidence: 99%

Noncovalent π-stacked robust topological organic framework

Meng

Yang

Xiao

et al. 2020

Proc. Natl. Acad. Sci. U.S.A.

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“…P. Sozzani et al. demonstrated that weak host–guest interactions effectively modify robustness of nanochannel architecture 12. In view of this study, stronger host–guest interactions in inclusion crystals are thought to stabilise the host framework.…”

Section: Introductionmentioning

confidence: 64%

“…P. Sozzani et al demonstrated that weak host-guest interactions effectively modify robustness of nanochannel architecture. [12] In view of this study, stronger host-guest interactions in inclusion crystals are thought to stabilise the host framework. Fluorescence intensity is assumed to be enhanced by guest molecules in the case of a host framework composed of fluorophores.…”

Section: Introductionmentioning

confidence: 94%

Amphiphilic Inclusion Spaces for Various Guests and Regulation of Fluorescence Intensity of 1,8‐Bis(4‐aminophenyl)anthracene Crystals

Sugino

Hatanaka

Araki

et al. 2014

Chemistry A European J

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A host framework for inclusion of various guest molecules was investigated by preparation of inclusion crystals of 1,8-bis(4-aminophenyl)anthracene (1,8-BAPA) with organic solvents. X-ray crystallographic analysis revealed construction of the same inclusion space incorporating 1,8-BAPA and eight guest molecules including both non-polar (benzene) and polar guests (N,N-dimethylformamide, DMF). Fluorescence efficiencies varied depending on guest molecule polarity; DMF inclusion crystals exhibited the highest fluorescence intensity (ΦF=0.40), four times as high as that of a benzene inclusion crystal (ΦF=0.10). According to systematic investigations of inclusion phenomena, strong host–guest interactions and filling of the inclusion space led to a high fluorescence intensity. Temperature-dependent fluorescence spectral measurements revealed these factors effectively immobilised the host framework. Although hydrogen bonding commonly decreases fluorescence intensity, the present study demonstrated that such strong interactions provide excellent conditions for fluorescence enhancement. Thus, this remarkable behaviour has potential application toward sensing of highly polar molecules, such as biogenic compounds.

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“…6 Moreover, TPP can be used as building blocks for preparation of assembled materials. 7 As a result of its unique features, organic zeolites and molecular self-assembled materials seem to constitute a competing alternative for strategic industrial and environmental applications such as gas storage, selective gas recognition, and separation, where absorption properties of materials are emerging at the forefront of present-day research. 8À10 For example, TPP nanochannels show a strong affinity for including simple-shaped gas molecular and aliphatic or aromatic molecules.…”

Section: ' Introductionmentioning

confidence: 99%

Solubilities of Tris(o-phenylenedioxy)cyclotriphosphazene in Selected Solvents

2011

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Tris-(o-phenylenedioxy)-cyclotriphosphazene (TPP) was synthesized and characterized by elemental analysis (EA) and nuclear magnetic resonance (NMR). The melting point and the enthalpy of fusion of TPP were measured by da ifferential scanning calorimeter (DSC), and the thermal stability of TPP was measured by thermogravimetric analysis (TGA). Using a static analytical method, the solubility data of TPP in nine solvents were measured and correlated with an empirical equation. Moreover, using the ScatchardÀHildebrand model, activity coefficients have also been calculated and compared with the experimental values. The partial molar excess enthalpies at infinite dilution were also predicted. ' INTRODUCTIONCyclophosphazene has a cycle structure comprised of nitrogen and phosphorus atoms. Many studies of flame retardants have focused attention on these atoms. The flame retardants reported in many papers have these heteroatoms. 1,2 Hence, the phosphazene structure has good flame retardant properties, and cyclophosphazene compounds could be used as flame retardants. 3,4 Tris-(o-phenylenedioxy)-cyclotriphosphazene (hereafter abbreviated as TPP; its formula is shown in Scheme 1) (CAS RN 311-03-5) is a cyclophosphazene derivative and could be used as a nonhalogen flame retardant for acrylonitrile butadiene styrene (ABS) 5 and poly(butylene terephthalate) (PBT). 6 Moreover, TPP can be used as building blocks for preparation of assembled materials. 7 As a result of its unique features, organic zeolites and molecular self-assembled materials seem to constitute a competing alternative for strategic industrial and environmental applications such as gas storage, selective gas recognition, and separation, where absorption properties of materials are emerging at the forefront of present-day research. 8À10 For example, TPP nanochannels show a strong affinity for including simple-shaped gas molecular and aliphatic or aromatic molecules. 11À13 The onedimensional arrangement of functional molecules using the TPP nanochannel is particularly interesting from the point of view of developing new molecular devices. 14 TPP can be prepared according to the literature. 15 In the industrial process and design, knowledge of solubilities of these compounds in different solvents is very important for their preparation and purification. To the best of our knowledge, the solubilities of TPP in selected solvents have not been reported in the literature.In this study, TPP was synthesized and characterized. The solubilities of TPP in ethanol, ethyl acetate, acetone, dichlormethane, tetrahydrofuran (THF), acetonitrile, toluene, chloroform, and 1,2-dichlorethane were also measured.

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A Family of Supramolecular Frameworks of Polyconjugated Molecules Hosted in Aromatic Nanochannels

Cited by 24 publications

References 45 publications

Noncovalent π-stacked robust topological organic framework

Noncovalent π-stacked robust topological organic framework

Amphiphilic Inclusion Spaces for Various Guests and Regulation of Fluorescence Intensity of 1,8‐Bis(4‐aminophenyl)anthracene Crystals

Solubilities of Tris(o-phenylenedioxy)cyclotriphosphazene in Selected Solvents

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