Supramolecular gels based on monopyrrolotetrathiafulvalene and its TCNQ charge-transfer complex

Liu, Yucun; Zheng, Ningjuan; Li, Hongda; Yin, Bo

doi:10.1039/c3sm50614b

Cited by 28 publications

(19 citation statements)

References 71 publications

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“…The studies showed that T 1 and T 2 gels were not formed in several common solvents such as hexane, chloroform, dichloromethane, tetrahydrofuran, toluene, diethyl ether, acetone, dimethylformamide, ethanol, methanol and acetonitrile when they were heated and cooled by the methods reported in the literature [ 2 – 4 ]. A loose gel of T 1 was observed in ethyl acetate when the concentration was increased to 20 mg/mL.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, the X-ray diffraction (XRD) patterns of T 1 and T 2 nanoribbons were taken ( Supporting Information File 1 , Figure S7). The XRD pattern of T 1 showed three sharp peaks at 7.4°, 14.9° and 22.1°, which suggested that a lamellar stacking organization was formed [ 4 ]. This was not the case for the XRD pattern of T 2 .…”

Section: Resultsmentioning

confidence: 99%

“…When one equivalent of TCNQ was added to the solution of T 1 in ethyl acetate, TCNQ radical anion species (TCNQ •− ) and TTF radical cation species (TTF •+ ) were formed, which was possibly supported by the increase of the absorption bands around 600–900 nm ( Fig. 5 ) [ 2 , 4 ]. Moreover, the UV–vis spectra of self-assembled nanoribbons doped with iodine were collected.…”

Section: Resultsmentioning

confidence: 99%

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Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

Sun

Lai

et al. 2015

Beilstein J. Org. Chem.

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SummaryThis paper reports the self-assembly of two new tetrathiafulvalene (TTF) derivatives that contain one or two urethane groups. The formation of nanoribbons was evidenced by scanning electron microscopy (SEM) and X-ray diffraction (XRD), which showed that the self-assembly ability of T 1 was better than that of T 2. The results revealed that more urethane groups in a molecule did not necessarily instigate self-assembly. UV–vis and FTIR spectra were measured to explore noncovalent interactions. The driving forces for self-assembly of TTF derivatives were mainly hydrogen bond interactions and π–π stacking interactions. The electronic conductivity of the T 1 and T 2 films was tested by a four-probe method.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

Sun

Lai

et al. 2015

Beilstein J. Org. Chem.

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“…Low-molecular-weight supramolecular gelators have been a topic of recent interest [65][66][67][68] owing to their fascinating selforganization properties and relevance in a range of applications including drug delivery, light harvesting, templating, organic photovoltaics, and others. D-A CT-interaction-promoted gelation has been studied in the recent past by many groups [69][70][71][72][73][74][75][76][77][78] including ours. [79,80] Gelation promoted by CT interactions was first reported by the group of Maitra in 1999.…”

Section: Gelation Driven By Ct Interactionsmentioning

confidence: 99%

“…[71][72][73][74] While these examples deal with gelation by only CT interactions, there is a significant interest in additionally using other supramolecular forces, such as hydrogen bonding, for formation of fibrillar two-component assemblies. TTF and its derivatives [75][76][77] are well-known donors with electroactive properties. They can be electrochemically/chemically oxidized to radical cations and dications, thus providing an additional opportunity to tune their self-assembly by an external stimuli.…”

Section: Gelation Driven By Ct Interactionsmentioning

confidence: 99%

Supramolecular Assemblies by Charge‐Transfer Interactions between Donor and Acceptor Chromophores

2014

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We have collated various supramolecular designs that utilize organic donor-acceptor CT complexation to generate noncovalently co-assembled structures including fibrillar gels, micelles, vesicles, nanotubes, foldamers, conformationally restricted macromolecules, and liquid crystalline phases. Possibly inspired by nature, chemists have extensively used hydrogen bonding as a tool for supramolecular assemblies of a diverse range of abiotic building blocks. As a structural motif, CT complexes can be compared to hydrogen-bonded complexes in its directional nature and complementarities. Additional advantages of CT interactions include wider solvent tolerance and easy spectroscopic probing. Nevertheless the major limitation is their low association constant. This article shows different strategies have evolved over the years to overcome this drawback by reinforcing the CT interactions with auxiliary noncovalent forces without hampering the alternate stacking mode. Emerging reports on promising CT complexes in organic electronics are intimately related to various supramolecular designs that one can postulate based on donor-acceptor CT interactions.

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Supramolekulare Anordnungen mit Charge‐Transfer‐Wechselwirkungen zwischen Donor‐ und Akzeptor‐Chromophoren

Das

Ghosh

2014

Angewandte Chemie

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In diesem Kurzaufsatz werden supramolekulare Anordnungen diskutiert, bei denen eine (nichtkovalente) Charge‐Transfer(CT)‐Wechselwirkung zwischen einem organischen Donor und Akzeptor genutzt wird, um Strukturen wie fibrilläre Gele, Micellen, Vesikel, Nanoröhren, Foldamere, konformativ eingeschränkte Makromoleküle und flüssigkristalline Phasen zu erzeugen. Nicht zuletzt auch nach dem Vorbild der Natur haben Chemiker die Wasserstoffbrücke als ein Hilfsmittel für die Herstellung von supramolekularen Anordnungen aus einer vielfältigen Auswahl an abiotischen Bausteinen umfassend genutzt. Als Strukturmotiv können CT‐Komplexe hinsichtlich ihrem gerichteten Charakter und ihrer Komplementarität mit Wasserstoffbrücken‐gebundenen Komplexen verglichen werden. Vorteile von CT‐Wechselwirkungen sind eine breite Lösungsmitteltoleranz und ihre einfache spektroskopische Messung. Ein potentieller Nachteil ist jedoch ihre geringe Assoziationskonstante. Um dieses Hindernis zu überwinden, wurden verschiedene Strategien entwickelt, z. B. die Verstärkung von CT‐Wechselwirkungen mit zusätzlichen nichtkovalenten Kräften, ohne dass die Art der Donor‐Akzeptor‐Stapelung beeinträchtigt wird. Ein besonders vielversprechendes Anwendungsfeld von Donor‐Akzeptor‐CT‐Komplexen ist die organische Elektronik.

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Supramolecular gels based on monopyrrolotetrathiafulvalene and its TCNQ charge-transfer complex

Cited by 28 publications

References 71 publications

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

Supramolecular Assemblies by Charge‐Transfer Interactions between Donor and Acceptor Chromophores

Supramolekulare Anordnungen mit Charge‐Transfer‐Wechselwirkungen zwischen Donor‐ und Akzeptor‐Chromophoren

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