A chemically and electrochemically switchable molecular shuttle

Bissell, Richard A.; Córdova, Emilio; Kaifer, Ángel E.; Stoddart, J. Fraser

doi:10.1038/369133a0

Cited by 1,201 publications

(750 citation statements)

References 25 publications

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“…[1][2][3][4] Various molecular systems in which translational or rotational motion of submolecular components takes place after chemical, electrochemical, electrical or photochemical excitation, have been described previously. [5][6][7][8][9][10][11][12][13][14] Up to now, most rotaxane-based submolecular motions have been studied in solution where the large possibility of orientation and ample freedom of movements are allowed. However, the creation of a rotaxane-based device requires the incorporation of rotaxane molecules in bidimensional arrays onto a surface, in a way that preserves the dynamic properties of the molecule.…”

Section: Introductionmentioning

confidence: 99%

Structural, Electrochemical, and Photophysical Properties of a Molecular Shuttle Attached to an Acid-Terminated Self-Assembled Monolayer

Cecchet¹,

Rudolf²,

Rapino³

et al. 2004

J. Phys. Chem. B

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Structural, electrochemical, and photophysical properties of a molecular shuttle attached to an acid-terminated self-assembled monolayer Cecchet, F; Rudolf, Petra; Rapino, S; Margotti, M; Paolucci, F; Baggerman, J; Kay, ER; Wong, JKY; Leigh, DA; Kay, Euan R. Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum. March 30, 2004; In Final Form: July 6, 2004 A benzylic amide macrocycle containing a pyridine moiety (macrocycle 2) and a related benzylic amide macrocycle-based molecular shuttle (naphthalimide rotaxane) with two pyridine moieties on the macrocyclic unit were grafted onto a self-assembled monolayer (SAM) of 11-mercaptoundecanoic acid (11-MUA) on gold. X-ray photoelectron spectroscopy (XPS) indicates that the molecules are linked to the SAM by hydrogenbonding. Electrochemical investigations show that the self-assembled monolayer is densely packed and well ordered and allows the estimation of the average thickness of the SAM alone and of the SAM functionalized with either macrocycle 2 or with naphthalimide rotaxane. The estimated thickness values suggest that the 11-MUA chains in the SAM are tilted with respect to the surface normal, as expected for ordered and stable SAMs, whereas the rotaxane molecules are oriented with the thread parallel to the SAM surface and macrocycle plan preferentially perpendicular to the surface. The photophysical studies of the naphthalimide rotaxane grafted onto the SAM on gold demonstrated that fluorescence is partially quenched but still remains easily measurable because the presence of the SAM reduces the quenching effect of the metal substrate. Moreover, the photophysical analysis clearly indicates that the naphthalimide part of the rotaxane strongly interacts with the carboxylic groups of the SAM, in agreement with the orientation of the molecule obtained from the electrochemistry.

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Section: Introductionmentioning

confidence: 99%

Structural, Electrochemical, and Photophysical Properties of a Molecular Shuttle Attached to an Acid-Terminated Self-Assembled Monolayer

Cecchet¹,

Rudolf²,

Rapino³

et al. 2004

J. Phys. Chem. B

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“…The latter are based on the observation that several of the interlocked structures prepared so far can change the relative positions of their component parts under external stimulus. Interlocked molecular rings, or catenanes, first made available through the pioneering work of Stoddart and Sauvage [2][3][4][5][6], occupy a special place in this category of new materials since their macrocycles can circumrotate one another like the rings of a macroscopic chain. This adds a degree of freedom not available to other systems that may find a role in the development of nanoscale devices such as molecular shuttles, switches and information storage systems (for review on electrooptically switchable catenanes, see [7]).…”

Section: Introductionmentioning

confidence: 99%

“…The synthesis and property characterization of supramolecular and molecular interlocked chemical objects is attracting a remarkable amount of interest [1][2][3][4][5][6][7], deriving on one hand from the often elegant strategies developed for their preparation, and on the other from practical, if not yet technological, considerations. The latter are based on the observation that several of the interlocked structures prepared so far can change the relative positions of their component parts under external stimulus.…”

Section: Introductionmentioning

confidence: 99%

Growth and characterization of benzylic amide [2]catenane thin films

et al. 1998

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We report here the first results on the thin-film growth of benzylic amide catenanes. The films were deposited onto gold single crystals by two different methods: by sublimation under ultra-high vacuum and by dipping of the substrate into a solution of the catenane. Sublimation yielded well-ordered films (domain diameter ∼100 Å ) while dipping produced disordered films. The vibrational and electronic properties of these films were investigated by high-resolution electron energy loss spectroscopy (HREELS) as a function of film thickness. The vibrational spectra indicate that the first layer of catenanes is chemisorbed.

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“…By 1994, Stoddart had modified the design so that the axle had two different binding sites 2 . The shuttle existed in solution; changing the acidity of this liquid forced the ring to hop from one site to the other, making the shuttle into a reversible switch.…”

Section: Shuttle Launchmentioning

confidence: 99%

The tiniest Lego: a tale of nanoscale motors, rotors, switches and pumps

Peplow¹

2015

Nature

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A chemically and electrochemically switchable molecular shuttle

Cited by 1,201 publications

References 25 publications

Structural, Electrochemical, and Photophysical Properties of a Molecular Shuttle Attached to an Acid-Terminated Self-Assembled Monolayer

Structural, Electrochemical, and Photophysical Properties of a Molecular Shuttle Attached to an Acid-Terminated Self-Assembled Monolayer

Growth and characterization of benzylic amide [2]catenane thin films

The tiniest Lego: a tale of nanoscale motors, rotors, switches and pumps

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