Chemically and Mechanically Controlled Single-Molecule Switches Using Spiropyrans

Mark C. Walkey, Chandramalika R. Peiris, Simone Ciampi, Albert C. Aragonès, Ruth B. Domínguez-Espíndola, David Jago, Thea Pulbrook, Brian W. Skelton, Alexandre N. Sobolev, Ismael Díez Pérez, Matthew J. Piggott, George A. Koutsantonis, Nadim Darwish

Research output: Contribution to journalArticle

Abstract

Developing molecular circuits that can function as the active components in electrical devices is an ongoing challenge in molecular electronics. It demands mechanical stability of the single-molecule circuit while simultaneously being responsive to external stimuli mimicking the operation of conventional electronic components. Here, we report single-molecule circuits based on spiropyran derivatives that respond electrically to chemical and mechanical stimuli. The merocyanine that results from the protonation/ring-opening of the spiropyran form showed single-molecule diode characteristics, with an average current rectification ratio of 5 at ±1 V, favoring the orientation where the positively charged end of the molecule is attached to the negative terminal of the circuit. Mechanical pulling of a single spiropyran molecule drives a switch to a more conducting merocyanine state. The mechanical switching is enabled by the strong Au-C covalent bonding between the molecule and the electrodes, which allows the tensile force delivered by the STM piezo to break the molecule at its spiropyran C-O bond.

Original languageEnglish
Pages (from-to)36886-36894
Number of pages9
JournalACS APPLIED MATERIALS & INTERFACES
Volume11
Issue number40
DOIs
Publication statusPublished - 9 Oct 2019

Cite this

Walkey, M. C., Peiris, C. R., Ciampi, S., C. Aragonès, A., Domínguez-Espíndola, R. B., Jago, D., ... Darwish, N. (2019). Chemically and Mechanically Controlled Single-Molecule Switches Using Spiropyrans. ACS APPLIED MATERIALS & INTERFACES, 11(40), 36886-36894. https://doi.org/10.1021/acsami.9b11044
Walkey, Mark C. ; Peiris, Chandramalika R. ; Ciampi, Simone ; C. Aragonès, Albert ; Domínguez-Espíndola, Ruth B. ; Jago, David ; Pulbrook, Thea ; Skelton, Brian W. ; Sobolev, Alexandre N. ; Díez Pérez, Ismael ; Piggott, Matthew J. ; Koutsantonis, George A. ; Darwish, Nadim. / Chemically and Mechanically Controlled Single-Molecule Switches Using Spiropyrans. In: ACS APPLIED MATERIALS & INTERFACES. 2019 ; Vol. 11, No. 40. pp. 36886-36894.
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Walkey, MC, Peiris, CR, Ciampi, S, C. Aragonès, A, Domínguez-Espíndola, RB, Jago, D, Pulbrook, T, Skelton, BW, Sobolev, AN, Díez Pérez, I, Piggott, MJ, Koutsantonis, GA & Darwish, N 2019, 'Chemically and Mechanically Controlled Single-Molecule Switches Using Spiropyrans' ACS APPLIED MATERIALS & INTERFACES, vol. 11, no. 40, pp. 36886-36894. https://doi.org/10.1021/acsami.9b11044

Chemically and Mechanically Controlled Single-Molecule Switches Using Spiropyrans. / Walkey, Mark C.; Peiris, Chandramalika R.; Ciampi, Simone; C. Aragonès, Albert; Domínguez-Espíndola, Ruth B.; Jago, David; Pulbrook, Thea; Skelton, Brian W.; Sobolev, Alexandre N.; Díez Pérez, Ismael; Piggott, Matthew J.; Koutsantonis, George A.; Darwish, Nadim.

In: ACS APPLIED MATERIALS & INTERFACES, Vol. 11, No. 40, 09.10.2019, p. 36886-36894.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Chemically and Mechanically Controlled Single-Molecule Switches Using Spiropyrans

AU - Walkey, Mark C.

AU - Peiris, Chandramalika R.

AU - Ciampi, Simone

AU - C. Aragonès, Albert

AU - Domínguez-Espíndola, Ruth B.

AU - Jago, David

AU - Pulbrook, Thea

AU - Skelton, Brian W.

AU - Sobolev, Alexandre N.

AU - Díez Pérez, Ismael

AU - Piggott, Matthew J.

AU - Koutsantonis, George A.

AU - Darwish, Nadim

PY - 2019/10/9

Y1 - 2019/10/9

N2 - Developing molecular circuits that can function as the active components in electrical devices is an ongoing challenge in molecular electronics. It demands mechanical stability of the single-molecule circuit while simultaneously being responsive to external stimuli mimicking the operation of conventional electronic components. Here, we report single-molecule circuits based on spiropyran derivatives that respond electrically to chemical and mechanical stimuli. The merocyanine that results from the protonation/ring-opening of the spiropyran form showed single-molecule diode characteristics, with an average current rectification ratio of 5 at ±1 V, favoring the orientation where the positively charged end of the molecule is attached to the negative terminal of the circuit. Mechanical pulling of a single spiropyran molecule drives a switch to a more conducting merocyanine state. The mechanical switching is enabled by the strong Au-C covalent bonding between the molecule and the electrodes, which allows the tensile force delivered by the STM piezo to break the molecule at its spiropyran C-O bond.

AB - Developing molecular circuits that can function as the active components in electrical devices is an ongoing challenge in molecular electronics. It demands mechanical stability of the single-molecule circuit while simultaneously being responsive to external stimuli mimicking the operation of conventional electronic components. Here, we report single-molecule circuits based on spiropyran derivatives that respond electrically to chemical and mechanical stimuli. The merocyanine that results from the protonation/ring-opening of the spiropyran form showed single-molecule diode characteristics, with an average current rectification ratio of 5 at ±1 V, favoring the orientation where the positively charged end of the molecule is attached to the negative terminal of the circuit. Mechanical pulling of a single spiropyran molecule drives a switch to a more conducting merocyanine state. The mechanical switching is enabled by the strong Au-C covalent bonding between the molecule and the electrodes, which allows the tensile force delivered by the STM piezo to break the molecule at its spiropyran C-O bond.

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KW - mechano-electronic switches

KW - molecular electronics

KW - single-molecule electronics

KW - single-molecule switches

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U2 - 10.1021/acsami.9b11044

DO - 10.1021/acsami.9b11044

M3 - Article

VL - 11

SP - 36886

EP - 36894

JO - Applied Materials and Interfaces

JF - Applied Materials and Interfaces

SN - 1944-8244

IS - 40

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Walkey MC, Peiris CR, Ciampi S, C. Aragonès A, Domínguez-Espíndola RB, Jago D et al. Chemically and Mechanically Controlled Single-Molecule Switches Using Spiropyrans. ACS APPLIED MATERIALS & INTERFACES. 2019 Oct 9;11(40):36886-36894. https://doi.org/10.1021/acsami.9b11044