Synthesis and Metal Ion Complexation Studies of [60]Fullerene Derivatives of Tetrathiafulvalene Crown Ethers

Liu, Sheng Gao; Echegoyen, Luis

doi:10.1002/1099-0690(200004)2000:7<1157::aid-ejoc1157>3.0.co;2-z

Cited by 29 publications

(22 citation statements)

References 18 publications

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“…These results indicate that the interaction of the metal ion with the dithia-crown ether must be responsible for the potential shifts. The recently published metal ion complexation studies of [60]fullerene derivatives of TTF-crown-ethers confirm this hypothesis (51). Although the C 60 -based reduction potentials are not affected by metal ion complexation because of the long distance between these centers, shifts were observed always for the TTF-centered oxidations, and these, as expected, were always anodic (more positive) (51).…”

Section: Resultssupporting

confidence: 58%

Metal ion recognition and molecular templating in self-assembled monolayers of cyclic and acyclic polyethers

Herranz

Colonna

Echegoyen

2002

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

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Our recent work with cyclic and acyclic polyether self-assembled monolayers (SAMs) on gold is presented. A series of dithia-crowntetrathiafulvalene derivatives with one or two disulfide groups has been prepared, and their SAMs on gold have been characterized by electrochemistry and by reflection-absorption infrared spectroscopy. These SAMs are extremely stable on repeated electrochemical potential scans and can selectively recognize alkali metal ions. Acyclic polyether derivatives can also self-assemble on gold to yield selective metal ion recognition domains. Impedance spectroscopy data for these SAMs fit the Langmuir isotherm and allow the determination of ion association constants. Some of the SAMs prepared with new acyclic polyether derivatives are able to detect potassium cations selectively when templated in their presence. These structures are believed to be a consequence of ion ''imprinting'' during the process of SAM formation.T he easy preparation, stability, and versatility of self-assembled monolayers (SAMs) has resulted in considerable activity in this field since the first publication by Nuzzo and Allara (1). Molecular recognition is especially relevant on surfaces because it allows the control of the exchange of signals, structures, and energy through the interfaces (2-4). SAMs allow the introduction of functional groups in the adsorbates, thus offering a powerful way to develop systems that have applications as sensors, devices, and switches (5). Some recent articles have reported surface structures with hydrophobic and hydrophilic properties arranged in nano-strips and honeycomb or homogeneous structures (6), whereas others have detected photo and electrochemical conversion of cis to trans forms within the SAM (7). Other examples have shown the formation of chiral imprinted sites (8). SAM structures have also been prepared for the recognition and sensing of metal ions (9), some of which are electrochemically active (10-18).Relatively recently, and Bryce et al. (23,24) reported, almost simultaneously, the incorporation of crownether groups into SAMs and their use as potential metal ion sensors. The Reinhoudt group used electrochemical impedance spectroscopy (EIS) for SAM characterization and to study the ion recognition processes (19)(20)(21)(22). This technique enables the detection of interfacial ion recognition phenomena when both guest ion and host monolayer are electrochemically inactive, by detecting changes of the charge-transfer resistance induced by metal ion binding (see Fig. 1a; refs. 25 and 26). The report by Bryce et al. (23,24) described SAMs of crown-annelated tetrathiafulvalene (TTF) derivatives, which showed, by cyclic voltammetry (CV), a redox potential shift of the electroactive, surface-confined, crown-TTF group on ion complexation (23, 24). The first TTF-crown SAMs reported by this group were apparently unstable after several electrochemical scans (23). However, in a subsequent report they demonstrated that the stability and electrochemical behavior of the SAMs can be improv...

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Section: Resultssupporting

confidence: 58%

Metal ion recognition and molecular templating in self-assembled monolayers of cyclic and acyclic polyethers

Herranz

Colonna

Echegoyen

2002

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

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“…Other receptors which, like 4, incorporate a crown-ether unit fused on two vicinal positions of TTF, have been described, 31 and also present moderate electrochemical responses to metal binding (DE 1 1/2 o 25 mV) whereas complexation does occur. Such observations underscore the importance of the molecular design and the crucial role of the connection in between the binding site and TTF redox-active readout element.…”

Section: Ttf-based Redox-responsive (-Switchable) Ligands For Cationic Guestsmentioning

confidence: 99%

Tetrathiafulvalene (TTF) derivatives: key building-blocks for switchable processes

et al. 2009

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Besides a traditional use for the development of organic conducting materials, the tetrathiafulvalene (TTF) unit and its derivatives have recently appeared as key constituents for new applications, exploiting remarkable redox properties: a high pi-donating ability and occurrence of three stable redox states. Indeed, in very recent years, an impressive variety of switchable TTF-based molecular and supramolecular (multifunctional) architectures have been designed and synthesized. In this feature article, we discuss recent developments of TTF-based molecular and supramolecular systems in this respect, including molecular sensors, redox-fluorescent switches, multi-input systems for logic gates, electrochemically-driven conformational controls, molecular clips and tweezers, and redox-controlled gelation processes.

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“…Subsequently, route A (the system KI/18-crown-6 was only replaced by Bu4NI) was exploited by Echegoyen and coll. [56] to introduce a crown-ether grafted at the periphery of the TTF core (26h-i). X-ray crystallography on 2-thioxo-1,3-dithiole-C60 adduct 25b showed the half-chair conformation of the cyclohexene ring and the presence of short intramolecular S•••C distances (3.9-4.0 Å) between sulfur atoms of the dithiole ring and the closest carbon atom of C60 [45].…”

Section: Diels-alder Reaction For Linking Ttf Onto C60mentioning

confidence: 99%

Diels–Alder cycloaddition as an efficient tool for linking π-donors onto fullerene C60

Hudhomme

2006

Comptes Rendus. Chimie

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Synthesis and Metal Ion Complexation Studies of [60]Fullerene Derivatives of Tetrathiafulvalene Crown Ethers

Cited by 29 publications

References 18 publications

Metal ion recognition and molecular templating in self-assembled monolayers of cyclic and acyclic polyethers

Metal ion recognition and molecular templating in self-assembled monolayers of cyclic and acyclic polyethers

Tetrathiafulvalene (TTF) derivatives: key building-blocks for switchable processes

Diels–Alder cycloaddition as an efficient tool for linking π-donors onto fullerene C60

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