Halogen bonding regulated functional nanomaterials

Zheng, Jie; Suwardi, Ady; Wong, Claris Jie Ee; Loh, Xian Jun; Liu, Yupeng

doi:10.1039/d1na00485a

Cited by 26 publications

(23 citation statements)

References 124 publications

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“…171,172 Interfacial XB or ChB optical sensors remain even more embryonic; the only example being the benzoselenadiazole bres developed by Che for uorescent gas sensing. 131 Clearly there is signicant untapped potential in further exploration of XB and ChB (sensing) materials, 182,183 particularly in thin lms and (interfacial) polymers [184][185][186] in electrochemical, optical and other sensing formats.…”

Section: Device and Materials Integrationmentioning

confidence: 99%

Halogen bonding and chalcogen bonding mediated sensing

Hein

Beer

2022

Chem. Sci.

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Section: Device and Materials Integrationmentioning

confidence: 99%

Halogen bonding and chalcogen bonding mediated sensing

Hein

Beer

2022

Chem. Sci.

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“…Among various types of σ -hole interactions, halogen bonds (XBs) are among the most known and widely investigated [ 1 , 2 , 3 , 4 ]. XBs were shown to play a significant role in organocatalysis [ 5 , 6 , 7 , 8 ], crystal engineering and supramolecular chemistry [ 9 , 10 , 11 , 12 , 13 ], materials science [ 14 , 15 , 16 , 17 ], stabilization of explosives [ 18 ], drug design [ 19 , 20 ], etc. XBs R–X⋯A (X—halogen) are formed between an electron-depleted region on the continuation of the R–X bond and an electron-rich region of another atom or molecule A ( Figure 1 , bottom).…”

Section: Introductionmentioning

confidence: 99%

The Distance between Minima of Electron Density and Electrostatic Potential as a Measure of Halogen Bond Strength

et al. 2022

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In this study, we present results of a detailed topological analysis of electron density (ED) of 145 halogen-bonded complexes formed by various fluorine-, chlorine-, bromine-, and iodine-containing compounds with trimethylphosphine oxide, Me3PO. To characterize the halogen bond (XB) strength, we used the complexation enthalpy, the interatomic distance between oxygen and halogen, as well as the typical set of electron density properties at the bond critical points calculated at B3LYP/jorge-ATZP level of theory. We show for the first time that it is possible to predict the XB strength based on the distance between the minima of ED and molecular electrostatic potential (ESP) along the XB path. The gap between ED and ESP minima exponentially depends on local electronic kinetic energy density at the bond critical point and tends to be a common limiting value for the strongest halogen bond.

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“…卤键作为一种强的静电相互作用力, 最初基于卤键的研究主要集中于控制超分子自组装 [1][2][3][4][5][6][7] . 近年来, 卤键的应用已从晶体工程 [8][9][10] 拓展到备受关注的有机催化 [11][12][13][14] 、功能材料 [15][16][17][18][19] 以及含卤药物的设计 [20][21][22] 等领域. 超分子螺旋和超分子大环在小分子和离子的跨膜运输 [23][24][25][26][27][28][29] 和识别客体分子 [30][31][32] 方面取得了很多的研究成果.…”

Section: 引言unclassified

Self-assembly of Supramolecular Planar Macrocycle Driven by Intermolecular Halogen Bonding

Liu¹,

Li²,

Wang³

et al. 2022

Acta Chimica Sinica

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The design and synthesis of three kinds of arylamide molecules (compounds 1～3) containing halogen bonding donor and acceptor fragments, and the exploration and analyzation of different action modes of halogen bonding in solid phase were reported. Compounds 1 and 2 contain two tetrafluoroiodobenzene fragments, and compound 1 also contains a halogen receptor fragment-pyridine group. Isobutyl groups are introduced into the molecule to increase its solubility and crystallinity. And a pyrimidine fragment was introduced into compound 3, which has more aromatic rings. The two N atoms of the pyrimidine fragment can theoretically form intramolecular hydrogen bonds with the adjacent amide hydrogen atoms (-C(＝O)NH), so that the whole molecule has the properties of hydrogen-bonded arylamide foldamer. Moreover, trifluorobenzene fragments were selected in compound 3 to eliminate the repulsion between excess fluorine atoms and carbonyls. The crystal structures reveal that the three aromatic rings in compound 1 are twisted with each other for there is no intramolecular hydrogen bond, and a supramolecular DNA-like double helix was assembled controlled by intermolecular N…I and O…I halogen bonds arranged alternately. Compound 2 failed to form an intramolecular three-center hydrogen bonding due to the repulsion between the amide carbonyl groups and the two fluorine atoms in close proximity. As expected, in the solid phase of compound 3, an effective three-center hydrogen bond is formed between the terminal trifluoroiodobenzene and the benzene ring attached to it. Moreover, the two N-H bonds connected to the pyrimidine ring also form two effective three-center hydrogen bonds. The difference is that the participants of these two groups of three-center hydrogen bonds include two N atoms in the pyrimidine ring. The four aromatic rings in compound 3 are nearly coplanar driven by these intramolecular three-center hydrogen bonds. Two sets of strong intermolecular (pyridine ring) N…I halogen bonds control the formation of [1＋1] bimolecular supramolecular macrocycles with inner diameters of 1.36 nm and 1.07 nm in length and width. Moreover, the supramolecular macrocycle is near-planar due to the introduction of pyrimidine ring.

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Halogen bonding regulated functional nanomaterials

Abstract: Non-covalent interactions have gained increasing attention for the use as a driving force to fabricate various supramolecular architectures, exhibiting great potential in crystal and materials engineering and supramolecular chemistry. As...

Cited by 26 publications

References 124 publications

Halogen bonding and chalcogen bonding mediated sensing

Halogen bonding and chalcogen bonding mediated sensing

The Distance between Minima of Electron Density and Electrostatic Potential as a Measure of Halogen Bond Strength

Self-assembly of Supramolecular Planar Macrocycle Driven by Intermolecular Halogen Bonding

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