Issue 44, 2023

Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches

Abstract

To achieve the ultimate limit of device miniaturization, it is necessary to have a comprehensive understanding of the structure–property relationship in functional molecular systems used in single-molecule electronics. This study reports the synthesis and characterization of a novel series of norbornadiene derivatives capped with thioether and thioester anchor groups. Utilizing the mechanically controllable break junction technique, the impact of these capping groups on conductance across single-molecule junctions is investigated. Among the selection of anchor groups, norbornadiene capped with thioacetate and tert-butyl groups exhibits higher conductance (G ≈ 4 × 10−4 G0) compared to methyl thioether (G ≈ 2 × 10−4 G0). Electronic transmission through the considered set of single-molecule junctions has been simulated. The computational results for electron transport across these junctions align closely with the experimental findings, with the thioacetate- and tert-butyl-substituted systems outperforming the methyl thioether-capped derivative. In terms of junction stability, the methyl thioether-capped system is the most resilient, maintaining consistent conductance even after approximately 10 000 cycles. Meanwhile, the likelihood of observing molecular plateaus in both the thioacetate- and tert-butyl-substituted systems declines over time. These findings substantially advance both the design and understanding of functional molecular systems in the realm of single-molecule electronics, particularly in the context of molecular photoswitches.

Graphical abstract: Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches

Supplementary files

Article information

Article type
Paper
Submitted
26 Jul 2023
Accepted
04 Oct 2023
First published
05 Oct 2023
This article is Open Access
Creative Commons BY license

J. Mater. Chem. C, 2023,11, 15412-15418

Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches

S. Ghasemi, L. Ornago, Z. Liasi, M. B. Johansen, T. J. von Buchwald, A. E. Hillers-Bendtsen, S. van der Poel, H. Hölzel, Z. Wang, F. M. Amombo Noa, L. Öhrström, K. V. Mikkelsen, H. S. J. van der Zant, S. Lara-Avila and K. Moth-Poulsen, J. Mater. Chem. C, 2023, 11, 15412 DOI: 10.1039/D3TC02652C

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