Electrochemistry of Supramolecular Systems

Boulas, Pierre; Gómez‐Kaifer, Marielle; Echegoyen, Luis

doi:10.1002/(sici)1521-3773(19980216)37:3<216::aid-anie216>3.0.co;2-p

Cited by 322 publications

(37 citation statements)

References 86 publications

(126 reference statements)

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“…During the past decades, tetrathiafulvalene (TTF) and its derivatives (TTFs) as building blocks in both conducting molecular materials and supramolecular chemistry [2][3][4] have been attracted increasing attention since the discovery of the first metallic charge transfer (CT) complex between TTF and 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) [5]. On account of the hybrid organic-inorganic materials, CT salts based on TTFs have been widely investigated in the search for new and improved superconducting CT complexes and radical cation salts [6,7].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 4,5-bis(2-bromineethylsulfanyl)-1,3-dithiole-2-thione, C7H8Br2S5

Zhao¹,

Song²,

Qin³

2008

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialTo a solution of 4,5-bis(2-hydroxyethylsulfanyl)-1,3-dithiole-2-thione [1] (2.86 g, 10 mmol) and CBr 4(8.3 g, 25 mmol) in dichloromethane (100 ml) was drop-added a solution of PPh 3 (6.56 g, 25 mmol) in the same solvent (20 ml) within 2 hours. The mixture was stirred at room temperature for 7 hours. The resulting solution was washed with water and dried over Na 2SO4. The solvent was then evaporated under reduced pressure and the crude product was purified by column chromatography (dichloromethane : petroleum ether = 2 : 3) to afford the title compound as yellow solid. DiscussionDuring the past decades, tetrathiafulvalene (TTF) and its derivatives (TTFs) as building blocks in both conducting molecular materials and supramolecular chemistry [2-4] have been attracted increasing attention since the discovery of the first metallic charge transfer (CT) complex between TTF and 7,7,8, [5]. On account of the hybrid organic-inorganic materials, CT salts based on TTFs have been widely investigated in the search for new and improved superconducting CT complexes and radical cation salts [6,7].TTFs serve as important p-electron donors for the development of molecular-based organic metals and superconductors, and a variety of studies on modification of the TTF skeleton have been made [8][9][10]. There are many routes for the preparation of TTFs. Generally, the most widely used is the coupling of two identical or non-identical 1,3-dithiole-2-(thi)ones mediated by a trivalent phosphorus derivative [11]. As important precursors of TTF derivatives, 1,3-dithiole-2-thiones have also attracted attention [12]. In the molecule of the title compound, the bond lengths and angles are within normal ranges [13]. In the crystal structure, adjacent molecules are linked by weak intermolecular C−H···S interactions (C···S distances: 3.7676(4) and 3.7932(4) Å, respectively) [14] into a chain, which extends into a two dimensional supramolecular architecture via weak inter-chain interactions of Br···Br (Br···Br distances: 3.731(1) and 3.889(1) Å, respectively) [13]. The adjacent layers are further interconnected into a interleaved three-dimensional supramolecular architecture by weak interactions of S···S and Br···S, with S···S distance range from 3.527(2) to 3.796(2) Å and a Br···S distance of 3.700(2) Å [13]. In addition, dipole-dipole and van der Waals interactions are also effective in the molecular packing.

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 4,5-bis(2-bromineethylsulfanyl)-1,3-dithiole-2-thione, C7H8Br2S5

Zhao¹,

Song²,

Qin³

2008

Zeitschrift Für Kristallographie - New Crystal Structures

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“…We conclude that although the classical definition of supramolecular chemistry as the chemistry beyond the molecule [31] is quite useful in general, functionally the distinction between what is molecular and what is supramolecular should be better based on the degree of intercomponent electronic interactions [50, 53,[55][56][57][58][59][60]. This concept is illustrated, for example, in Figure 1.5 [57].…”

Section: Supramolecular (Multicomponent) Chemistrymentioning

confidence: 99%

Introduction

2008

Molecular Devices and Machines

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“…Electrochemical methods have been used extensively to control molecular recognition [6,7,9,10,16,22,43,[95][96][97][98][99]. As discussed in Section 10.4.3, electrochemical techniques can be used not only to induce chemical or conformational changes in supramolecular systems but also to probe their superstructures and organization.…”

Section: Electrochemically Driven Movementsmentioning

confidence: 99%

“…Cyclodextrins [71] are a class of hosts that are inactive electrochemically yet can form stable pseudorotaxanes with a variety of electroactive guests [9,11,97,99,100]. It has been found, for example, that, although bipyridinium-containing compounds in the dicationic forms (e.g., 5 2þ , Figure 14.6) are not bound by b-cyclodextrin (b-CD), when reduced to their monocationic forms they interact weakly with the cavity of this host and give fairly stable pseudorotaxane complexes with b-CD when they are finally reduced to their uncharged forms [101].…”

Section: Electrochemically Driven Movementsmentioning

confidence: 99%

Linear Movements

2008

Molecular Devices and Machines

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Electrochemistry of Supramolecular Systems

Cited by 322 publications

References 86 publications

Crystal structure of 4,5-bis(2-bromineethylsulfanyl)-1,3-dithiole-2-thione, C7H8Br2S5

Crystal structure of 4,5-bis(2-bromineethylsulfanyl)-1,3-dithiole-2-thione, C7H8Br2S5

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