Dataset Information

Supramolecular Hydrogen Bonding Assembly from Non-Coplanar Aromatic Tetra-¹H-Pyrazoles with Crystallization-Induced Emission (CIE).

ABSTRACT: Here, we report a design strategy for constructing supramolecular organic frameworks by introducing ¹H-pyrazole groups to aromatic cores as non-coplanar molecules to form diverse supramolecular assemblies through multiple ¹H-pyrazole [N-H···N] hydrogen bonds as well as other weak interactions. The new supramolecular organic frameworks displayed interesting crystallization-induced emission (CIE) behavior.

SUBMITTER: Wang J

PROVIDER: S-EPMC9026852 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Publications

Supramolecular Hydrogen Bonding Assembly from Non-Coplanar Aromatic Tetra-1H-Pyrazoles with Crystallization-Induced Emission (CIE).

Wang Ji J Zhao Li-Rong LR Tong Jin J Yu Yan-Min YM Wang Xia-Yan XY Yu Shu-Yan SY

International journal of molecular sciences 20220411 8

Here, we report a design strategy for constructing supramolecular organic frameworks by introducing 1H-pyrazole groups to aromatic cores as non-coplanar molecules to form diverse supramolecular assemblies through multiple 1H-pyrazole [N-H···N] hydrogen bonds as well as other weak interactions. The new supramolecular organic frameworks displayed interesting crystallization-induced emission (CIE) behavior. ...[more]

PMID: 35457024

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Project description:Carbon, although the central element in organic chemistry, has been traditionally neglected as a target for directional supramolecular interactions. The design of supramolecular structures involving carbon-rich molecules, such as arene hydrocarbons, has been limited almost exclusively to non-directional π-stacking, or derivatisation with heteroatoms to introduce molecular assembly recognition sites. As a result, the predictable assembly of non-derivatised, carbon-only π-systems using directional non-covalent interactions remains an unsolved fundamental challenge of solid-state supramolecular chemistry. Here, we propose and validate a different paradigm for the reliable assembly of carbon-only aromatic systems into predictable supramolecular architectures: not through non-directional π-stacking, but via specific and directional halogen bonding. We present a systematic experimental, theoretical and database study of halogen bonds to carbon-only π-systems (C-I⋯πC bonds), focusing on the synthesis and structural analysis of cocrystals with diversely-sized and -shaped non-derivatised arenes, from one-ring (benzene) to 15-ring (dicoronylene) polycyclic atomatic hydrocarbons (PAHs), and fullerene C60, along with theoretical calculations and a systematic analysis of the Cambridge Structural Database. This study establishes C-I⋯πC bonds as directional interactions to arrange planar and curved carbon-only aromatic systems into predictable supramolecular motifs. In >90% of herein presented structures, the C-I⋯πC bonds to PAHs lead to a general ladder motif, in which the arenes act as the rungs and halogen bond donors as the rails, establishing a unique example of a supramolecular synthon based on carbon-only molecules. Besides fundamental importance in the solid-state and supramolecular chemistry of arenes, this synthon enables access to materials with exciting properties based on simple, non-derivatised aromatic systems, as seen from large red and blue shifts in solid-state luminescence and room-temperature phosphorescence upon cocrystallisation.

Dataset Information

Supramolecular Hydrogen Bonding Assembly from Non-Coplanar Aromatic Tetra-¹H-Pyrazoles with Crystallization-Induced Emission (CIE).

Publications

Supramolecular Hydrogen Bonding Assembly from Non-Coplanar Aromatic Tetra-<sup>1</sup>H-Pyrazoles with Crystallization-Induced Emission (CIE).

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