An approach to insulated molecular wires: synthesis of water-soluble conjugated rotaxanes

Anderson, S.; Aplin, Robin T.; Claridge, Tim D. W.; Goodson, Theodore; Maciel, Angela C.; Rumbles, Garry; Ryan, John F.; Anderson, Harry L.

doi:10.1039/a802680g

Cited by 80 publications

(69 citation statements)

References 72 publications

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“…In the case of polyrotaxanes, the polymer chains are terminated by two bulky stoppers which prevent the macrocycles from slipping off. Over the last years, much work has been devoted to the study of cyclodextrin-based polyrotaxanes or pseudopolyrotaxanes, concerning both non-conjugated polymers [2][3][4][5][6] and conjugated oligomers or polymer chains [7][8][9][10][11][12][13][14][15][16][17]. These latter can be considered as ''insulated molecular wires''.…”

Section: Introductionmentioning

confidence: 99%

Electropolymerization of cyclodextrin/4-aminobiphenyl inclusion complex generating water-soluble pseudo-oligorotaxanes in their oxidized state

Bergamini

Jouini

Aeiyach

et al. 2005

Journal of Electroanalytical Chemistry

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Section: Introductionmentioning

confidence: 99%

Electropolymerization of cyclodextrin/4-aminobiphenyl inclusion complex generating water-soluble pseudo-oligorotaxanes in their oxidized state

Bergamini

Jouini

Aeiyach

et al. 2005

Journal of Electroanalytical Chemistry

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“…When exploiting the electronic functionality of single molecules it is important to prevent cross-talk, and the design of molecularly isolated conducting structures may enable the size of electronic circuits to be reduced to molecular dimensions. [9] Insulated molecular wires have been created by threading conjugated polymers through cyclophanes, [10,11] cyclodextrins [12] and zeolites, [9,13] by wrapping them in polymer helices, [14] and by decorating them with dendritic side-chains. [15] Here, we present some polyrotaxanes [16] consisting of a conjugated polymer core threaded through a series of cyclodextrin macrocycles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Conjugated Polyrotaxanes

Michels

O’Connell

Taylor

et al. 2003

Chemistry A European J

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151

109

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A series of conjugated polyrotaxane insulated molecular wires are synthesised by aqueous Suzuki polymerisation, using hydrophobic binding to promote threading of the cyclodextrin units. These polyrotaxanes have conjugated polymer cores based on poly(para-phenylene), polyfluorene, and poly(diphenylene-vinylene), threaded through 0.9-1.6 cyclodextrins per repeat unit. Bulky naphthalene-3,6-disulfonate endgroups prevent the macrocycles from slipping off the conjugated polymer chains. Dialysis experiments show that the cyclodextrins become unthreaded only if smaller stoppers are used. MALDI TOF mass spectra detect oligomers with up to ten threaded cyclodextrins, and reveal the presence of some defects that result for oxidative homo-coupling of boronic acids. Weight-average molecular weights were determined by analytical ultracentrifugation, demonstrating that step-growth polymerisation is efficient enough to achieve degrees of polymerisation up to approximately 20 repeat units (84 para-phenylenes). The fluorescence spectra of these polyrotaxanes indicate that the presence of the threaded cyclodextrin macrocycles reduces the flexibility of the conjugated polymer pi-systems. Both the solution and the solid-state photoluminescence quantum yields are enhanced upon threading of the conjugated polyaromatic cores through alpha- or beta-cyclodextrins, and the emission spectra of the polyrotaxanes are blue-shifted compared to the corresponding unthreaded polymers. The greater weight of the 0-0 transition in the emission spectra, as well as the smaller Stokes shift, indicate that the polyrotaxanes are more rigid than the unthreaded polymers.

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“…30,31,33 Finally, for the case of no energy migration ͑or intermolecular interaction͒ the depolarization rate should follow the rotational diffusion of the dendrimer molecule in solution, which is relatively long for large molecules. 35 Similar to the approach often taken in describing the dynamics of photosynthetic systems, the coherence of excitation in dendrimers can be analyzed by the two limiting cases of Förster transfer and that of completely delocalized excitonic states. The bridge between the two limiting cases is a parameter that describes the interaction energy ͑J͒ divided by the homogeneous linewidth ⌫.…”

Section: Introductionmentioning

confidence: 99%

Investigations of excitation energy transfer and intramolecular interactions in a nitrogen corded distrylbenzene dendrimer system

Varnavski

Samuel

Pålsson

et al. 2002

The Journal of Chemical Physics

113

174

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Articles you may be interested inEnergy transfer rates and population inversion of I 4 11 / 2 excited state of Er 3 + investigated by means of numerical solutions of the rate equations system in Er : LiYF 4 crystal J. Appl. Phys. 106, 103508 (2009) The photophysics of an amino-styrylbenzene dendrimer ͑A-DSB͒ system is probed by time-resolved and steady state luminescence spectroscopy. For two different generations of this dendrimer, steady state absorption, emission, and photoluminescence excitation spectra are reported and show that the efficiency of energy transfer from the dendrons to the core is very close to 100%. Ultrafast time-resolved fluorescence measurements at a range of excitation and detection wavelengths suggest rapid ͑and hence efficient͒ energy transfer from the dendron to the core. Ultrafast fluorescence anisotropy decay for different dendrimer generations is described in order to probe the energy migration processes. A femtosecond time-scale fluorescence depolarization was observed with the zero and second generation dendrimers. Energy transfer process from the dendrons to the core can be described by a Förster mechanism ͑hopping dynamics͒ while the interbranch interaction in A-DSB core was found to be very strong indicating the crossover to exciton dynamics.

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An approach to insulated molecular wires: synthesis of water-soluble conjugated rotaxanes

Cited by 80 publications

References 72 publications

Electropolymerization of cyclodextrin/4-aminobiphenyl inclusion complex generating water-soluble pseudo-oligorotaxanes in their oxidized state

Electropolymerization of cyclodextrin/4-aminobiphenyl inclusion complex generating water-soluble pseudo-oligorotaxanes in their oxidized state

Synthesis of Conjugated Polyrotaxanes

Investigations of excitation energy transfer and intramolecular interactions in a nitrogen corded distrylbenzene dendrimer system

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