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  • Molecular recognition  (3)
  • Self-assembly  (3)
  • molecular devices  (3)
  • 1995-1999  (9)
  • 1
    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: 1434-1948
    Keywords: Grid complexes ; Self-assembly ; Co ; Zn ; Coordination chemistry ; Bis(tridentate) ligands ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The tretrametallic [2 × 2] grid-type complexes 1-4 are formed by self-assembly of the bis(tridentate) ligands 5 and 6 with ZnII and CoII cations. They have been characterized by spectroscopic studies in solution as well as by crystal structure determination. The substituents in the central pyrimidine ring play an important role in terms of geometry and physical properties of the complexes. They induce an orthogonal orientation of the ligand in the complexes which is critical for the formation of ordered monolayers and extended self-organized arrays of grids. The physical properties of the complexes such as metal-metal interaction and π-π* stacking between the ligands may be modulated by changing these substituents.
    Additional Material: 6 Ill.
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  • 3
    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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  • 4
    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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  • 5
    ISSN: 1434-193X
    Keywords: Cyclo-bis-intercaland ; Acridine units ; cis/trans-Azobenzene dicarboxylic acids ; Inclusion compounds ; X-ray structure ; Molecular recognition ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The water soluble acyclic 1 and macrocyclic 2 receptor molecules, based on acridine units, form 1:1 complexes with the cis- or trans-2,2′ and 3,3′-azobenzene dicarboxylate substrates. The stability constants of these complexes, determined by 1H NMR spectroscopy, cover a wide range from 30 to 105M-1, thus displaying very pronounced structure selectivity with respect to both substitution pattern and cis, transconfiguration. The complexes of the cyclo-bis-intercaland receptor 2 are two or three orders of magnitude more stable than those of 1. The inclusion complex of cyclo-bis-intercaland 2 with trans-3,3′- azobenzene dicarboxylate has been isolated and its structure has been determined by X-ray crystallography using synchrotron radiation, confirming the intercalation of the substrate between the acridine residues in the species formed.
    Additional Material: 3 Ill.
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  • 6
    ISSN: 1434-193X
    Keywords: Dynamic combinatorial chemistry ; Molecular recognition ; Hydrogen bonding ; Hydrazone isomerization ; Barbiturate receptor ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The selection of the receptor presenting the strongest affinity for a barbiturate substrate from a dynamic combinatorial library of constituents differing in structure and conformation/configuration is described. The gradual addition of the barbiturate to an equilibrating mixture of hydrazone isomers leads to the quantitative shift towards a single species, 3, which presents highest complementarity to the substrate and yields the supramolecular entity 3:4.
    Additional Material: 2 Ill.
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  • 7
    ISSN: 1434-1948
    Keywords: Helicates ; Oligobipyridine ligands ; Self-recognition ; NMR titration ; Self-assembly ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oligobipyridine ligands containing one or two imine bridges were found to form double helicates by treatment with copper(I) or silver(I). The properties of the complexes are similar to those of oxapropylene-bridged oligobipyridines. Titration of a mixture of the bis(bipyridine) and the tris(bipyridine) ligands with silver(I) hexafluorophosphate showed that helicates formed with strict self-recognition.
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  • 8
    ISSN: 1434-1948
    Keywords: Combinatorial chemistry ; Molecular recognition ; Functionalized bipyridine metal complexes ; Janus molecules ; Hydrogen bonding ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The functionalized ligands 1 and 2 bearing hydrogen-bonding recognition groups have been synthesized. Their assembly by metal ions such as CuI and PdII having different coordination geometries generates different receptor architectures for the binding of suitable substrates. Addition of the complementary bis(imide) Janus molecules (4-7) to [1a, 2a, CuTf] or to [1b, 2b, Pd(BF4)2] mixtures leads to a moderate selective increase of the fraction of the [(1a)2Cu]+ or [(1b)2Pd]2+ complex depending on the Janus substrate used. Largest enhancements are observed for those Janus substrates that may be expected to display highest geometrical complementarity with the two complexes. These results represent a process directed by target binding based on dynamic combinatorial chemistry.
    Additional Material: 5 Ill.
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  • 9
    ISSN: 1434-1948
    Keywords: Self-assembly ; Tetranuclear CuII complex ; [2 × 2] grid-type complex ; Crystal structure ; Magnetic properties ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The ditopic ligand 3 has been synthesized. In its deprotonated form, it reacts with copper(II) ions to form a tetranuclear complex 1 of the [2 × 2] CuII4 grid type, the structure of which has been confirmed by X-ray crystallography. Magnetic studies of complex 1 indicate a very weak antiferromagnetic coupling between the phenoxo-bridged CuII ions.
    Additional Material: 3 Ill.
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