Hexagonal array formation by intermolecular halogen bonding using a binary blend of linear building blocks: STM study

Kikkawa, Yoshihiro; Nagasaki, Mayumi; Koyama, Emiko; Tsuzuki, Seiji; Hiratani, Kazuhisa

doi:10.1039/c9cc00532c

Cited by 22 publications

(26 citation statements)

References 41 publications

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“…When a slightly different halogen bond acceptor with a different position of the pyridinic nitrogen was used, no porous networks were obtained. This observation highlighted the importance of the design aspect which is intimately related to the directional nature of halogen bonds …”

Section: Halogen‐halogen Interactions and Halogen‐bonding In Self‐assmentioning

confidence: 94%

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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 Interactions and Halogen‐bonding In Self‐assmentioning

confidence: 94%

“…This observation highlighted the importance of the design aspect which is intimately related to the directional nature of halogen bonds. [34]…”

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

confidence: 99%

Halogen Bonding in Two‐Dimensional Crystal Engineering

2020

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“…Except for the change in the length of the alkyl chains, the building blocks of Py-Cn and FI-Cn (n ¼ 14 and 15) were prepared as reported previously. 35 Briey, for the preparation of Py-Cn, the alkylation of catechol with an alkyl bromide followed by iodination was performed to yield 1,2-bis(alkyloxy)-4-iodobenzene. Then, the Sonogashira coupling of 3-ethynylpyridine with 1,2bis(alkyloxy)-4-iodobenzene was performed in dry tetrahydrofuran with a Pd(PPh 3 ) 4 catalyst, CuI co-catalyst, and triethylamine.…”

Section: Preparation and Characterization Of Molecular Building Blocksmentioning

confidence: 99%

“…2B and S2 (ESI) †), as reported by many others. 35,[43][44][45][46][47][48] The total interaction energy of the 4 head groups (Fig. 2D) was calculated to be À20.2 kcal mol À1 (Fig.…”

Section: Bi-component Systemmentioning

confidence: 99%

“…[24][25][26][27][28][29][30][31][32][33][34] However, in most of these studies, the 2D porous networks were created via hydrogen bonding and dispersion interactions of alkyl chains using rigid molecular building blocks with C 3 symmetry. [27][28][29][30][31][32][33][34] In a previous study, 35 we prepared simple and linear molecular building blocks with halogen bonding acceptor and donor units (Py-Cn and FI-Cn (n ¼ 18), respectively, in Chart 1). The binary blends of Py-C18 and FI-C18 formed hexagonal and porous networks, as observed by STM, at the highly oriented pyrolytic graphite (HOPG)/1-phenyloctane interface.…”

Section: Introductionmentioning

confidence: 99%

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Dynamic host–guest behavior in halogen-bonded two-dimensional molecular networks investigated by scanning tunneling microscopy at the solid/liquid interface

et al. 2020

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Design of Trehalose‐Based Amide/Sulfonamide C‐type Lectin Receptor Signaling Compounds

et al. 2021

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Mincle agonists have been shown to induce inflammatory cytokine production, such as tumor necrosis factor-alpha (TNF) and promote the development of a Th1/Th17 immune response that might be crucial to development of effective vaccination against pathogens such as Mycobacterium tuberculosis. As an expansion of our previous work, a library of 6,6'-amide and sulfonamide α,α-d-trehalose compounds with various substituents on the aromatic ring was synthesized efficiently in good to excellent yields. These compounds were evaluated for their ability to activate the human C-type lectin receptor Mincle by the induction of cytokines from human peripheral blood mononuclear cells. A preliminary structure-activity relationship (SAR) of these novel trehalose diamides and sulfonamides revealed that aryl amide-linked trehalose compounds demonstrated improved activity and relatively high potency cytokine production compared to the Mincle ligand trehalose dibehenate adjuvant (TDB) and the natural ligand trehalose dimycolate (TDM) inducing dose-dependent and human-Mincle-specific stimulation in a HEK reporter cell line.

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Hexagonal array formation by intermolecular halogen bonding using a binary blend of linear building blocks: STM study

Abstract: A bicomponent blend of linear building blocks leads to intermolecular halogen bonding, resulting in the formation of hexagonal arrays.

Cited by 22 publications

References 41 publications

Halogen Bonding in Two‐Dimensional Crystal Engineering

Halogen Bonding in Two‐Dimensional Crystal Engineering

Dynamic host–guest behavior in halogen-bonded two-dimensional molecular networks investigated by scanning tunneling microscopy at the solid/liquid interface

Design of Trehalose‐Based Amide/Sulfonamide C‐type Lectin Receptor Signaling Compounds

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