TY - JOUR
T1 - Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches
AU - Ghasemi, Shima
AU - Ornago, L.
AU - Liasi, Zacharias
AU - van der Poel, S.
AU - Hölzel, Helen
AU - Wang, Zhihang
AU - van der Zant, H.S.J.
AU - Lara-Avila, Samuel
AU - Moth-Poulsen, Kasper
AU - More Authors, null
PY - 2023
Y1 - 2023
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85175265367&partnerID=8YFLogxK
U2 - 10.1039/d3tc02652c
DO - 10.1039/d3tc02652c
M3 - Article
SN - 2050-7526
VL - 11
SP - 15412
EP - 15418
JO - Journal of Materials Chemistry C: materials for optical and electronic devices
JF - Journal of Materials Chemistry C: materials for optical and electronic devices
IS - 44
ER -