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  • photochromes  (3)
  • N ligands  (2)
  • Supramolecular chemistry  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 2 (1996), S. 1399-1406 
    ISSN: 0947-6539
    Keywords: electrochromes ; fluorescence ; molecular devices ; oligothiophenes ; photochromes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The extended dithienylethene compounds 1-3 have been synthesized. They undergo photochromic and electrochemical changes by photoinduced interconversion between open and closed forms of type A and B. In addition, both forms of the N-methylated derivatives 1b and 2b have absorption bands in which excitation results in very large differences in fluorescence between the two forms with very little effect on the opening/closing state, a feature of interest for optical memory data systems. The compounds 2 and 3 contain six and eight conjugated thiophene units in the closed forms, respectively, and thus represent oligothiophenes endowed with a photoactivated switch; they are of special interest in this respect in view of the potential use of switched oligothiophenes in molecular electronic devices.
    Additional Material: 7 Ill.
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  • 2
    ISSN: 0947-6539
    Keywords: diarylethenes ; molecular devices ; nonlinear optics ; photochromes ; redox switches ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Organic photochromic systems represent a starting point for the elaboration of light-triggered molecular switching devices. The novel bispyridinium and bispyridine compounds 12+ and 6 were synthesized as their uncyclized isomers from 3,5-dibromo-2-methylthiophene in overall yields of 43 and 44%, respectively. The diarylethene photochromes 2 and 10-13, substituted with electron donors and acceptors, were prepared from 5-methylthiophene-2-carboxaldehyde in 21-32% overall yield. All of the compounds were found to exhibit pronounced photochromic properties. Irradiation with UV light resulted in essentially complete photocyclization of the open forms to the intensely coloured closed isomers which could, in turn, be reconverted back to the open state with visible light of γ〉600 nm. The absorption maxima of the described compounds in their closed forms are shifted far towards, and even into, the near-IR region. Whereas no thermochromic properties were observed for the open isomers, the rates of thermal decolouration of the cyclized forms was found to be highly dependent on the nature of the substituents on the thiophene rings. It was demonstrated that reversible photochemical interconversion between the two photochromic states could be used to effectively switch a number of physical properties. Thus, the molecules 12+ and 12 represent two kinds of redox switches, the former in reduction and the latter in oxidation, in which electron conduction is switched on in the closed state and off in the open state. Compound 12 may also be considered to be a photoswitchable analogue of tetrathiafulvalene type substances. On the other hand, compound 2 displays a marked increase in nonlinear optical activity on conversion from the open to the closed form. Such systems are prototypes of photoswitchable molecular wires where electron conduction and push-pull interaction can be reversibly modulated by an external stimulus, namely, irradiation by light.
    Additional Material: 10 Ill.
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  • 3
    ISSN: 0947-6539
    Keywords: diarylethenes ; electrochromes ; molecular devices ; optical memory ; photochromes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The bisphenolic dithienylethene molecules 1a and 1b were synthesized in overall yields of 45% from 4-bromoanisole and 44% from 2.6-di-tert-butyl-4-iodophenol, respectively. The corresponding extended quinones 3a and 3b were also prepared. Photochemical studies showed that compounds 1 are photochromic; the open forms 1 could be converted with UV light of 312nm to the closed coloured forms 2 with photostationary states lying at essentially complete conversion (〉 98%). The 1a-2a system was found to exhibit good resistance to photofatigue and thermal stability for both photoisomers. Cyclic voltammetry studies involving the 2/3 couples showed that whereas 2b undergoes irreversible oxidation at + 0.85 V (vs. SCE in THF), the hydroquinone 2a is reversibly oxidized at an E1/2 of + 0.72V (in MeCN, quasi-reversibly in THF at + 0.81 V); this reflects the differences in deprotonation behaviour of the generated QH2/2+ species. The large difference in oxidation potential between 1a and 2a allows the photochemical switching of redox properties. In a complementary fashion, redox switching of the photochromic properties within the 2a-3a pair is possible since 3a is stable to visible light. Owing to this unique behaviour, the triad consisting of 1-3a represents a novel molecular device with mutually regulating photo- and electrochromic behaviour. In addition, the ability to interconvert between the three stable states makes the system well-suited as the basis for an optical memory system with multiple storage and nondestructive readout capacity through a write-lock-read-unlock-erase cycle.
    Additional Material: 11 Ill.
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  • 4
    ISSN: 0570-0833
    Keywords: cobalt ; coordination modes ; N ligands ; supramolecular chemistry ; tetranuclearcomplexes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
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  • 5
    ISSN: 0570-0833
    Keywords: coordination modes ; multinuclear complexes ; N ligands ; self-assembly ; silver ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
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  • 6
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 29 (1990), S. 1304-1319 
    ISSN: 0570-0833
    Keywords: Self-assembly ; Information processing ; Molecular information processing ; Molecular recognition ; Supramolecular chemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The selective binding of a substrate by a molecular receptor to form a supramolecular species involves molecular recognition which rests on the molecular information stored in the interacting species. The functions of supermolecules cover recognition, as well as catalysis and transport. In combination with polymolecular organization, they open ways towards molecular and supramolecular devices for information processing and signal generation. The development of such devices requires the design of molecular components performing a given function (e.g., photoactive, electroactive, ionoactive, thermoactive, or chemoactive) and suitable for assembly into an organized array. Light-conversion devices and charge-separation centers have been realized with photoactive cryptates formed by receptors containing photosensitive groups. Eleclroactive and ionoactive devices are required for carrying information via electronic and ionic signals. Redox-active polyolefinic chains, like the “caroviologens”, represent molecular wires for electron transfer through membranes. Push-pull polyolefins possess marked nonlinear optical properties. Tubular mesophases, formed by organized stacking of suitable macro-cyclic components, as well as “chundle”-type structures, based on bundles of chains grafted onto a macrocyclic support, represent approaches to ion channels. Lipophilic macrocyclic units form Langmuir-Blodgett films that may display molecular recognition at the air-water interface. Supramolecular chemistry has relied on more or less preorganized molecular receptors for effecting molecular recognition, catalysis, and transport processes. A step beyond preorganization consists in the design of systems undergoing self-organization, that is, systems capable of spontaneously generating a well-defined supramolecular architecture by self-assembling from their components under a given set of conditions. Several approaches to self-assembling systems have been pursued: the formation of helical metal complexes, the double-stranded helicates, which result from the spontaneous organization of two linear polybipyridine ligands into a double helix by binding of specific metal ions; the generation of mesophases and liquid crystalline polymers of supramolecular nature from complementary components, amounting to macroscopic expression of molecular recognition; the molecular-recognition-directed formation of ordered solid-state structures. Endowing photo-, electro-, and ionoactive components with recognition elements opens perspectives towards the design of programmed molecular and supramolecular systems capable of self-assembly into organized and functional supramolecular devices. Such systems may be able to perform highly selective operations of recognition, reaction, transfer, and structure generation for signal and information processing at the molecular and supramolecular levels.
    Additional Material: 15 Ill.
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  • 7
    ISSN: 0570-0833
    Keywords: Supramolecular chemistry ; Nobel lecture ; Macrocycles ; Molecular recognition ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Supramolecular chemistry is the chemistry of the intermolecular bond, covering the structures and functions of the entities formed by association of two or more chemical species. Molecular recognition in the supermolecules formed by receptor-substrate binding rests on the principles of molecular complementarity, as found in spherical and tetrahedral recognition, linear recognition by coreceptors, metalloreceptors, amphiphilic receptors, and anion coordination. Supramolecular catalysis by receptors bearing reactive groups effects bond cleavage reactions as well as synthetic bond formation via cocatalysis. Lipophilic receptor molecules act as selective carriers for various substrates and make it possible to set up coupled transport processes linked to electron and proton gradients or to light. Whereas endoreceptors bind substrates in molecular cavities by convergent interactions, exoreceptors rely on interactions between the surfaces of the receptor and the substrate; thus new types of receptors, such as the metallonucleates, may be designed. In combination with polymolecular assemblies, receptors, carriers, and catalysts may lead to molecular and supramolecular devices, defined as structurally organized and functionally integrated chemical systems built on supramolecular architectures. Their recognition, transfer, and transformation features are analyzed specifically from the point of view of molecular devices that would operate via photons, electrons, or ions, thus defining fields of molecular photonics, electronics, and ionics. Introduction of photosensitive groups yields photoactive receptors for the design of light-conversion and charge-separation centers. Redox-active polyolefinic chains represent molecular wires for electron transfer through membranes. Tubular mesophases formed by stacking of suitable macrocyclic receptors may lead to ion channels. Molecular self-assembling occurs with acyclic ligands that form complexes of double-helical structure. Such developments in molecular and supramolecular design and engineering open perspectives towards the realization of molecular photonic, electronic, and ionic devices that would perform highly selective recognition, reaction, and transfer operations for signal and information processing at the molecular level.
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