Supramolecular Cl⋅⋅⋅H and O⋅⋅⋅H Interactions in Self‐Assembled 1,5‐Dichloroanthraquinone Layers on Au(111)

Noh, Seung Kyun; Jeon, Jeong Heum; Jang, Won Jun; Kim, Howon; Lee, Soon Hyeong; Lee, Min Wook; Lee, Jhinhwan; Han, Seungwu; Kahng, Se-Jong

doi:10.1002/cphc.201201061

Cited by 19 publications

(10 citation statements)

References 37 publications

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“…This comparative study illustrated that hydrogen bonding interactions and close packing considerations overrule relatively weak halogen-halogen interactions such as the ClÀ Cl type II contacts. [38] Halogen-halogen type-II contacts have been recently employed to generate exotic supramolecular architectures such as fractals. Fractals are complex patterns that are self-similar across different length scales.…”

Section: Halogen-halogen and Halogen-heteroatoms Interactions At The mentioning

confidence: 99%

Halogen Bonding in Two‐Dimensional Crystal Engineering

2020

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Halogen bonds, which provide an intermolecular interaction with moderate strength and high directionality, have emerged as a promising tool in the repertoire of non‐covalent interactions. In this review, we provide a survey of the literature where halogen bonding was used for the fabrication of supramolecular networks on solid surfaces. The definitions of, and the distinction between halogen bonding and halogen‐halogen interactions are provided. Self‐assembled networks formed at the solution/solid interface and at the vacuum‐solid interface, stabilized in part by halogen bonding, are discussed. Besides the broad classification based on the interface at which the systems are studied, the systems are categorized further as those sustained by halogen‐halogen and halogen‐heteroatom contacts.

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Section: Halogen-halogen and Halogen-heteroatoms Interactions At The mentioning

confidence: 99%

Halogen Bonding in Two‐Dimensional Crystal Engineering

2020

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“…Halogen-bonded (XB) molecular nanostructures 1,[7][8][9] are considerably less common in on-surface 2D systems but are increasingly being studied and seen as an important addition to the 'toolbox' of supramolecular assembly. Typically, iodine [10][11][12][13][14] and bromine atoms [15][16][17][18][19] are used as halogen bond donors due to their strong polarisability, but examples of chlorine 20 and fluorine 21,22 based assemblies have also been reported. Halogen bonds can also involve halogen atoms acting simultaneously as both donor and acceptor 11,16,17,23,24 , with the positive electrostatic potential of the sigma hole oriented towards the central 'belt' of negative electrostatic potential found on an adjacent halogen atom.…”

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confidence: 99%

Combining high-resolution scanning tunnelling microscopy and first-principles simulations to identify halogen bonding

et al. 2020

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Scanning tunnelling microscopy (STM) is commonly used to identify on-surface molecular self-assembled structures. However, its limited ability to reveal only the overall shape of molecules and their relative positions is not always enough to fully solve a supramolecular structure. Here, we analyse the assembly of a brominated polycyclic aromatic molecule on Au(111) and demonstrate that standard STM measurements cannot conclusively establish the nature of the intermolecular interactions. By performing high-resolution STM with a COfunctionalised tip, we clearly identify the location of rings and halogen atoms, determining that halogen bonding governs the assemblies. This is supported by density functional theory calculations that predict a stronger interaction energy for halogen rather than hydrogen bonding and by an electron density topology analysis that identifies characteristic features of halogen bonding. A similar approach should be able to solve many complex 2D supramolecular structures, and we predict its increasing use in molecular nanoscience at surfaces.

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“…The former can be greater or less than the latter. [15][16][17] In earlier work studying XB and HB between DMSO and three fluorobenzene derivatives(C 6 F 5 H, C 6 F 5 Cl, ClC 6 F 4 H), using both experimental and theoretical approaches, we found that HB was stronger than XB in these binary systemsi fc hlorine was the halogen. [18] Considering that the strength of the bromine-(BrÀXB) and iodine-based halogen bonds (IÀXB) are normally greatert han that of chlorine-based halogen bonds (ClÀXB), we extend our work to these two cases herein.…”

Section: Introductionmentioning

confidence: 91%

“…Noh et al found that both XB and HB could contributep ositively to stabilization of the supramolecular structures. [16] Li et al found that there was significant cooperativity between XB and HB in some complexes. [17] Nevertheless, the electronic structures of the halogen atoms are quite different from that of the hydrogen atom.…”

Section: Introductionmentioning

confidence: 98%

Comparative Study of Halogen‐ and Hydrogen‐Bond Interactions between Benzene Derivatives and Dimethyl Sulfoxide

et al. 2015

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The halogen bond, similar to the hydrogen bond, is an important noncovalent interaction and plays important roles in diverse chemistry-related fields. Herein, bromine- and iodine-based halogen-bonding interactions between two benzene derivatives (C6 F5 Br and C6 F5 I) and dimethyl sulfoxide (DMSO) are investigated by using IR and NMR spectroscopy and ab initio calculations. The results are compared with those of interactions between C6 F5 Cl/C6 F5 H and DMSO. First, the interaction energy of the hydrogen bond is stronger than those of bromine- and chlorine-based halogen bonds, but weaker than iodine-based halogen bond. Second, attractive energies depend on 1/r(n) , in which n is between three and four for both hydrogen and halogen bonds, whereas all repulsive energies are found to depend on 1/r(8.5) . Third, the directionality of halogen bonds is greater than that of the hydrogen bond. The bromine- and iodine-based halogen bonds are strict in this regard and the chlorine-based halogen bond only slightly deviates from 180°. The directional order is iodine-based halogen bond>bromine-based halogen bond>chlorine-based halogen bond>hydrogen bond. Fourth, upon the formation of hydrogen and halogen bonds, charge transfers from DMSO to the hydrogen- and halogen-bond donors. The CH3 group contributes positively to stabilization of the complexes.

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Supramolecular Cl⋅⋅⋅H and O⋅⋅⋅H Interactions in Self‐Assembled 1,5‐Dichloroanthraquinone Layers on Au(111)

Cited by 19 publications

References 37 publications

Halogen Bonding in Two‐Dimensional Crystal Engineering

Halogen Bonding in Two‐Dimensional Crystal Engineering

Combining high-resolution scanning tunnelling microscopy and first-principles simulations to identify halogen bonding

Comparative Study of Halogen‐ and Hydrogen‐Bond Interactions between Benzene Derivatives and Dimethyl Sulfoxide

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