Abstract:The effect of the in-backbone presence of charge-assisted hydrogen bonds (CAHBs) in the conductance of single-molecule junctions has been studied by the scanning tunneling microscope break junction technique. In particular, two amidinium−carboxylate supramolecular complexes of different lengths have been tested. We observed that the ionic character that gives extra stability to the CAHB is a hindrance toward the electron transport through the complexes. Theoretical calculations using the DFT + Σ method indicat… Show more
“… Schematics of typical H‐bonded junctions from DNA base pairs to Upy dimer (a–d) [10, 63] . Schematic of CAHBs junction (e) and the 1D conductance histograms of monomer (f, blue) and dimer (f, purple) [34b] . (g) Localized electron distribution of CAHBs dimer.…”
Section: Supramolecular Junctions With Non‐covalent Interactionsmentioning
confidence: 99%
“…studied the effect of charge‐assisted hydrogen bonds (CAHBs) on H‐bonded junctions (Figure 14e). [34b] CAHBs means that ion‐charged H‐donor and H‐acceptor enhance the hydrogen bond strength. Experimental studies found that the formation probability of SMe‐anchored CAHBs junctions reaches up to 67 %.…”
Section: Supramolecular Junctions With Non‐covalent Interactionsmentioning
The convergence of supramolecular chemistry and single-molecule electronics offers a new perspective on supramolecular electronics, and provides a new avenue toward understanding and application of intermolecular charge transport at the molecular level. In this review, we will provide an overview of the advances in the characterization technique for the investigation of intermolecular charge transport, and summarize the experimental investigation of several non-covalent interactions, including π-π stacking interactions, hydrogen bonding, host-guest interactions and σ-σ interactions at the single-molecule level. We will also provide a perspective on supramolecular electronics and discuss the potential applications and future challenges.
“… Schematics of typical H‐bonded junctions from DNA base pairs to Upy dimer (a–d) [10, 63] . Schematic of CAHBs junction (e) and the 1D conductance histograms of monomer (f, blue) and dimer (f, purple) [34b] . (g) Localized electron distribution of CAHBs dimer.…”
Section: Supramolecular Junctions With Non‐covalent Interactionsmentioning
confidence: 99%
“…studied the effect of charge‐assisted hydrogen bonds (CAHBs) on H‐bonded junctions (Figure 14e). [34b] CAHBs means that ion‐charged H‐donor and H‐acceptor enhance the hydrogen bond strength. Experimental studies found that the formation probability of SMe‐anchored CAHBs junctions reaches up to 67 %.…”
Section: Supramolecular Junctions With Non‐covalent Interactionsmentioning
The convergence of supramolecular chemistry and single-molecule electronics offers a new perspective on supramolecular electronics, and provides a new avenue toward understanding and application of intermolecular charge transport at the molecular level. In this review, we will provide an overview of the advances in the characterization technique for the investigation of intermolecular charge transport, and summarize the experimental investigation of several non-covalent interactions, including π-π stacking interactions, hydrogen bonding, host-guest interactions and σ-σ interactions at the single-molecule level. We will also provide a perspective on supramolecular electronics and discuss the potential applications and future challenges.
Comprehensive SummaryHydrogen bonding is a vital driving force for organizing the hierarchy of molecular structure, especially in biologic field. Due to its directionality, selectivity and moderate strength, hydrogen bonding has been extensively introduced into the molecular recognition, sensing and electronic devices. Electric measurements at single‐molecule level facilitate the investigation of hydrogen bonds and provide a comprehensive understanding of the electron transport properties governed by the hydrogen bonding, which is essential for the development of self‐assembled electronic systems. This review provides a detailed overview of recent advancements in constructing single‐molecule junctions utilizing intramolecular and intermolecular hydrogen bonding. We first introduce the methods utilized for characterizing the electric and dynamic properties of non‐covalent interactions. Next, we discuss the mechanisms of electron transport, relevant influencing factors, and typical applications utilizing electrical signals based on single‐molecule junctions. Finally, we propose our perspective on the existing challenges and prospective opportunities in utilizing hydrogen bonding for electronic device applications.This article is protected by copyright. All rights reserved.
“…[ 14,20 ] The building units of CAHONs often possess the acid and base sites, in other words, the acidity and basicity of involved ligands are generally selected as oppositely charged building units for constructing stable CAHONs. [ 21‐23 ] It is well‐known that carboxylic acid can be deprotoned and becomes the anionic building block, while the viologen often possesses the positive charges, which is a good candidate for the cationic building unit. [ 24‐26 ] The combination of the electron‐rich carboxylic acid and the electron‐deficient viologen is an efficient method for probing the novel CAHONs with specific functional properties.…”
Section: Background and Originality Contentmentioning
Comprehensive Summary
Hydrogen‐bonded organic networks (HONs) have attracted intense research interest due to their mild synthesis conditions, good solvent processability and strong reproducibility. Most HONs are constructed by electrically neutral organic ligands through intermolecular interactions such as weak hydrogen bonding, π‐π stacking. But there are a few charge‐assisted hydrogen‐bonding networks (CAHONs) constructed by oppositely charged organic components. Under hydrothermal conditions, we successfully synthesized a 3D CAHON (H2CV)(H2BTEC) (1) constructed by H2CV (CV = N,N′‐4,4′‐bipyridine dipropionate) and H4BTEC (H4BTEC = 1,2,4,5‐benzenetetracarboxylic acid) through multiple charge‐assisted hydrogen bonding. Upon soft X‐ray, ultraviolet light or sunlight irradiation under ambient conditions, 1 quickly changes from colorless to blue (1P), and kinetic calculations show that its photochromism meets first‐order dynamics. Interestingly, the colored crystals 1P with long‐lived colored radicals will not fade after being placed for more than two months at room temperature in air, owing to the fact that the photogenerated viologen radicals can be stabilized by the abundant hydrogen bonds, the coplanar pyridinium rings and the slow electron‐hole recombination. Moreover, 1 is a typical direct band gap semiconductor, evidenced by the calculated band gap of 3.24 eV, in agreement with the experimental value of 3.40 eV. In view of its strong colored stability, 1 is designed for distinctive inkless printing.
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