Pnictogen bonding in imide derivatives for chiral folding and self-assembly

Wang, Zhuoer; Cao, Zhaozhen; Hao, Aiyou; Xing, Pengyao

doi:10.1039/d4sc00554f

Chem. Sci.

2024

DOI: 10.1039/d4sc00554f

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Pnictogen bonding in imide derivatives for chiral folding and self-assembly

Zhuoer Wang,

Zhaozhen Cao,

Aiyou Hao

et al.

Abstract: Pnictogen bonding (PnB) is an attraction interaction that originates from the anisotropic distribution of electron density of pnictogen elements, which however has been rarely found in nitrogen atoms. In this...

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Cited by 6 publications

References 53 publications

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Anions as Lewis Acids in Noncovalent Bonds

Scheiner

2024

Chemistry A European J

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The ability of an anion to serve as electron‐accepting Lewis acid in a noncovalent bond is assessed via DFT calculations. NH3 is taken as the common base, and is paired with a host of ACln‐ anions, with central atom A = Ca, Sr, Mg, Te, Sb, Hg, Zn, Ag, Ga, Ti, Sn, I, and B. Each anion reacts through its σ or π‐hole although the electrostatic potential of this hole is quite negative in most cases. Despite the contact between this negative hole and the negative region of the approaching nucleophile, the electrostatic component of the interaction energy of each bond is highly favorable, and accounts for more than half of the total attractive energy. The double negative charge of dianions precludes a stable complex with NH3.

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Anions as Lewis Acids in Noncovalent Bonds

Scheiner

2024

Chemistry A European J

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High‐Fidelity Supramolecular Chirality Transportation Enabled Through Chalcogen Bonding

Wang,

Hao,

Xing

2024

Small

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The formation of asymmetric microenvironments in proteins benefits from precise transportation of chirality across multiple levels through weak bonds in the folding and assembly process, which inspires the rational design and fabrication of artificial chiral materials. Herein, the chalcogen bonding‐directed precise transportation of supramolecular chirality toward multiple levels is reported to aid the fabrication of chiroptical materials. Benzochalcogenadiazole (O, S, Se) motifs are conjugated to amino acid residues, and the solid‐state assemblies afforded selective supramolecular chirality with handedness depending on the kinds of chalcogen atoms and amino acids. The chalcogen‐N sequence assisted by hydrogen bonding synergistically allows for the complexation with pyrene conjugated aryl carboxylic acids to give macroscopic helical structures with active circular dichroism and circularly polarized luminescence, of which handedness is precisely determined by the pristine chiral species. Then the further application of chiral benzochalcogenadiazole motifs as seeds in directing handedness of benzamide via symmetry breaking is realized. Behaving as the dopants, embedding into the matrix of benzophenone induces the room temperature phosphorescence, whereby the thermal chiroptical switch is fabricated with color‐tunable phosphorescent circularly polarized luminescence. This work utilized benzochalcogenadiazole‐based chiral building units to accomplish precise transportation of supramolecular chirality in coassemblies with high‐fidelity, achieving flexible manipulation of chiroptical properties and macroscopic helical sense.

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Spodium Bonding to Dicoordinated Group 12 Atoms

Amonov,

Scheiner

2024

J. Phys. Chem. A

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DFT calculations consider the interactions between linear MR 2 and a series of N-bases, where M is Hg or Zn and its R substituents are CCH, CN, or NO 2 . NCH, NH 3 , and NMe 3 were considered as three different N-bases. Zn forms stronger bonds with the N bases than does Hg, and they strengthen along with the electron-withdrawing power of the R substituent, varying over a wide range from 3.4 to 43.9 kcal/mol. Another factor contributing to the bond strength is the nucleophilicity of the base: NCH < NH 3 < NMe 3 . All MR 2 Lewis acids can bind at least two bases, which are situated along the R-M-R bisecting plane, fairly close to one another, with θ(N-M-N) angles between 67°and 117°. The presence of a more electronwithdrawing substituent R and more powerful nucleophile allows up to 4 bases to bind to M. The properties of these bonds place them along a continuum, some clearly noncovalent, while other contain a good deal of covalent character.

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Pnictogen bonding in imide derivatives for chiral folding and self-assembly

Abstract: Pnictogen bonding (PnB) is an attraction interaction that originates from the anisotropic distribution of electron density of pnictogen elements, which however has been rarely found in nitrogen atoms. In this...

Cited by 6 publications

References 53 publications

Anions as Lewis Acids in Noncovalent Bonds

Anions as Lewis Acids in Noncovalent Bonds

High‐Fidelity Supramolecular Chirality Transportation Enabled Through Chalcogen Bonding

Spodium Bonding to Dicoordinated Group 12 Atoms

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