Bottom-up assembly of a surface-anchored supramolecular rotor enabled using a mixed self-assembled monolayer and pre-complexed components

Puigmartí‐Luis, Josep; Saletra, Wojciech J.; González, Asensio; Amabilino, David B.; Pérez‐García, Lluïsa

doi:10.1039/c3cc44794d

Cited by 22 publications

(13 citation statements)

References 26 publications

(5 reference statements)

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“…The synthesis of Cu-DPP and Ni-DPP described by26 was modified by changing the solvent and reaction times (See SI for experimental details). PY was synthesized as described previously by Puigmarti-Luis et al 27. and the single-molecule transport measurements were conducted following the procedure described in ref.…”

Section: Resultsmentioning

confidence: 99%

Tuning the electrical conductance of metalloporphyrin supramolecular wires

Noori

Aragonès

Palma

et al. 2016

Sci Rep

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In contrast with conventional single-molecule junctions, in which the current flows parallel to the long axis or plane of a molecule, we investigate the transport properties of M(II)-5,15-diphenylporphyrin (M-DPP) single-molecule junctions (M=Co, Ni, Cu, or Zn divalent metal ions), in which the current flows perpendicular to the plane of the porphyrin. Novel STM-based conductance measurements combined with quantum transport calculations demonstrate that current-perpendicular-to-the-plane (CPP) junctions have three-orders-of-magnitude higher electrical conductances than their current-in-plane (CIP) counterparts, ranging from 2.10−2 G0 for Ni-DPP up to 8.10−2 G0 for Zn-DPP. The metal ion in the center of the DPP skeletons is strongly coordinated with the nitrogens of the pyridyl coated electrodes, with a binding energy that is sensitive to the choice of metal ion. We find that the binding energies of Zn-DPP and Co-DPP are significantly higher than those of Ni-DPP and Cu-DPP. Therefore when combined with its higher conductance, we identify Zn-DPP as the favoured candidate for high-conductance CPP single-molecule devices.

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Section: Resultsmentioning

confidence: 99%

Tuning the electrical conductance of metalloporphyrin supramolecular wires

Noori

Aragonès

Palma

et al. 2016

Sci Rep

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“…solution, vacuum and at interfaces), i.e., fabrication of rotors at the nanoscale could be tuned using i) radiation, ii) electric fields induced by the STM tips and even iii) oxidation-reduction reactions [60,61]. In the field of molecular motors, focus has been given to studies at room-temperature and some important contributions have been published with dynamic molecular systems in these conditions [61][62][63][64][65]. A recent work [63] reports a walking molecule moving freely at room-temperature between two stationary points.…”

Section: Molecular Motorsmentioning

confidence: 99%

Bottom-Up Self-Assembled Supramolecular Structures Built by STM at Solid/Liquid Interface

Ferreira¹,

Delfino²,

Morgado³

et al. 2018

Preprint

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The development of organic devices has been focused in their miniaturization in order to obtain denser and faster electronic circuits. The challenge is to build the devices adding atom by atom or molecule by molecule until the desired structure is achieved. To do this job, techniques able to see and manipulate matter at this scale are needed. Scanning tunneling microscopy has been the selected technique by scientists to develop smart and functional unimolecular devices. This review article compiles the latest developments in this field giving examples of supramolecular systems monitored and fabricated at molecular scale by bottom-up approaches using STM at solid/liquid interface.

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“…The effect of dilution on the supramolecular organization on the surface was investigated by STM. Among the different methods tested, the most efficient appeared to be the adsorption of a preformed supramolecular rotor, implying that an ordered SAM is not necessarily an ideal site for adsorption 104…”

Section: Redox‐driven Molecular Machines On Surfaces and In Confinmentioning

confidence: 99%

Size‐Induced Chiral Discrimination Switching by (S)‐(−)‐2(α‐Hydroxyethyl)Benzimidazole‐Derived Azacrowns

et al. 2014

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(S)‐(−)‐2‐(α‐Hydroxyethyl)benzimidazole (1)‐derived diastereomeric monoaza‐[18]crown‐6 compounds 5 and 6 were synthesised with an additional chiral centre bearing a phenyl ring. The aim was to achieve enhanced enantioselective discrimination, compared with monoaza‐[15]crown‐5 (7). Surprisingly, reversal of enantioselective binding for chiral guest enantiomers between the two differently sized [15]crown‐5 and [18]crown‐6 azacrowns were discovered; all three were prepared from the same parent compound, 1. To complete the observations, another [18]crown‐6‐sized azacrown (10) without an additional chiral centre was synthesised from 1 and screened for its enantioselective binding abilities towards the chiral guest enantiomers investigated; these results corroborated the observations. Single‐crystal XRD analysis and molecular docking studies revealed that changes to the conformational aspects of [18]crown‐6 and [15]crown‐5 azacrowns were the major contributing factors to this peculiar behaviour.

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Bottom-up assembly of a surface-anchored supramolecular rotor enabled using a mixed self-assembled monolayer and pre-complexed components

Abstract: Three different routes to rotor-type systems on a gold surface provide sparse and dense layers of rotors with best control exerted using mixed ordered monolayers that guide the creation of the potential molecular machine components from solution.

Cited by 22 publications

References 26 publications

Tuning the electrical conductance of metalloporphyrin supramolecular wires

Tuning the electrical conductance of metalloporphyrin supramolecular wires

Bottom-Up Self-Assembled Supramolecular Structures Built by STM at Solid/Liquid Interface

Size‐Induced Chiral Discrimination Switching by (S)‐(−)‐2(α‐Hydroxyethyl)Benzimidazole‐Derived Azacrowns

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