Synergistic effects of hydrogen and halogen bonding in co-crystals of dipyridylureas and diiodotetrafluorobenzenes

DeHaven, Baillie A.; Chen, Anna L.; Shimizu, Emily; Salpage, Sahan R.; Smith, Mark D.; Shimizu, Linda S.

doi:10.1080/10610278.2017.1364380

Cited by 10 publications

(12 citation statements)

References 32 publications

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“…The observed shifts between the free and bound molecules, for some IR vibrational bands, are presented in Table and Figure . In agreement with literature data, there is a shift of the band corresponding to the CN bond (around 1600 cm –1 ) of 1 , but it is small for all investigated cocrystals. According to the literature, the band around 1300 cm –1 was assigned to symmetric ring contraction of the halogen bonding donors.…”

Section: Resultssupporting

confidence: 91%

Halogen Bonds (N---I) at Work: Supramolecular Catemeric Architectures of 2,7-Dipyridylfluorene with ortho-, meta-, or para-Diiodotetrafluorobenzene Isomers

Grosu

Pop

Miclăuş

et al. 2020

Crystal Growth & Design

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Supramolecular assemblies of 2,7-dipyridylfluorene with diiodotetrafluorobenzene isomers were obtained by mechanochemical synthesis and their structures were determined by single crystal X-ray diffraction. The contribution of specific non-covalent interactions between different building blocks to the stability and solid-state packing behaviors of the supramolecular catemers was evaluated by theoretical methods, which confirm the geometries and interactional bonding observed in single crystal X-ray diffraction structures.

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Section: Resultssupporting

confidence: 91%

Halogen Bonds (N---I) at Work: Supramolecular Catemeric Architectures of 2,7-Dipyridylfluorene with ortho-, meta-, or para-Diiodotetrafluorobenzene Isomers

Grosu

Pop

Miclăuş

et al. 2020

Crystal Growth & Design

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“…Although similar halogen-bonding chains were observed in the 1 : 1 co-crystals of dipyridyl ureas (1,3-bis((pyridin-2/3/4-yl)methyl)urea ( o/m/p -BPyMU)) and 1,4-DITFB [ 72 ], the intermediate ureas behave differently from the sulfur atom and azo moiety stated above. They participate in the intermolecular N–H \documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{upgreek} \usepackage{mathrsfs} \setlength{\oddsidemargin}{-69pt} \begin{document} }{}$\cdots$\end{document} O interactions and induce the formation of 1D urea–urea hydrogen-bonding tapes.…”

Section: Co-crystallization Of 14-ditfb With Various Halogen-bonding Acceptorsmentioning

confidence: 63%

Halogen bonding in the co-crystallization of potentially ditopic diiodotetrafluorobenzene: a powerful tool for constructing multicomponent supramolecular assemblies

Ding

Chang

et al. 2020

National Science Review

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Halogen bond is emerging as a significant driving force for supramolecular self-assembly, and has aroused great interest during the last two decades. Among the diverse halogen-bonding donors, we take notice of the ability of 1,4-diiodotetrafluorobenzene (1,4-DITFB) to co-crystallize with diverse halogen-bonding acceptors in the range from neutral Lewis bases (nitrogen-containing compounds, N-oxides, chalcogenides, aromatic hydrocarbons and organometallic complexes) to anions (halide ions, thio/selenocyanate ions and tetrahedral oxyanions), leading to a great variety of supramolecular architectures such as discrete assemblies, 1D infinite chain and 2D/3D networks. Some of them act as promising functional materials (for instance, fluorescence, phosphorescence, optical waveguide, laser, nonlinear optics, dielectric and magnetism), and soft materials (e.g. liquid crystal and supramolecular gels). Here we focus on the supramolecular structures of multicomponent complexes and their related physicochemical properties, highlight representative examples, and show clearly the main directions which remain to be developed and improved in this area. From the point of view of crystal engineering and supramolecular chemistry, the complexes summarized here should give helpful information for further design and investigation on the elusive category of halogen-bonding supramolecular functional materials.

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“…Supramolecular organic co-crystal chemistry primarily focuses on various noncovalent interactions, such as hydrogen bonds, C–H···π, π···π, and charge-transfer interactions. − In addition to these, lp···π intermolecular interactions − have become significantly important due to their role in the stability of supramolecular and biomolecular entities . A viable co-crystal synthesis strategy , has the potency to induce some of the superior properties of the individual components by synergistic effects, , and hence, co-crystal preparation can modulate emission colors and luminescence efficiency. − …”

Section: Introductionmentioning

confidence: 99%

“…15−26 In addition to these, lp•••π intermolecular interactions 27−29 have become significantly important due to their role in the stability of supramolecular and biomolecular entities. 30 A viable co-crystal synthesis strategy 31,32 has the potency to induce some of the superior properties of the individual components by synergistic effects, 33,34 and hence, co-crystal preparation can modulate emission colors and luminescence efficiency. 35−38 It has been generally found that π-conjugated organic molecules consisting of electron-donating or -withdrawing substituents have the usual propensity to co-crystallize through π−π stacking interactions in two different packing motifs, namely, segregated stacking 39,40 and mixed stacking.…”

Section: ■ Introductionmentioning

confidence: 99%

Exploring the Relationship between Intermolecular Interactions and Solid-State Photophysical Properties of Organic Co-Crystals

et al. 2018

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Five new binary co-crystals have been prepared through molecular self-assembly of π-electron-rich molecules, such as phenanthrene, benzo[c]cinnoline, and phenazine, in the presence of π-electron-deficient molecules, such as tetrafluoro-1,4-benzoquinone, tetrachloro-1,4-benzoquinone, and 1,2,4,5-tetracyanobenzene, taken in an equimolar ratio. Crystal structure analysis revealed that in three binary co-crystals the constituent molecules were alternately sandwiched in a cofacial arrangement through π•••π interactions, whereas in the remaining two binary co-crystals the constituent molecules were aligned in a unique edge-to-face manner through lp•••π interactions. Co-crystals with π-stacking arrangement were fluorescent, whereas almost complete quenching of luminescence was observed in those having edge-to-face alignment of molecules. The photophysical observations of these co-crystals have been demonstrated via energetic quantification of the intermolecular interaction topology, which provides a molecular level understanding of factors controlling their solid-state absorption and luminescence behavior.

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Synergistic effects of hydrogen and halogen bonding in co-crystals of dipyridylureas and diiodotetrafluorobenzenes

Cited by 10 publications

References 32 publications

Halogen Bonds (N---I) at Work: Supramolecular Catemeric Architectures of 2,7-Dipyridylfluorene with ortho-, meta-, or para-Diiodotetrafluorobenzene Isomers

Halogen Bonds (N---I) at Work: Supramolecular Catemeric Architectures of 2,7-Dipyridylfluorene with ortho-, meta-, or para-Diiodotetrafluorobenzene Isomers

Halogen bonding in the co-crystallization of potentially ditopic diiodotetrafluorobenzene: a powerful tool for constructing multicomponent supramolecular assemblies

Exploring the Relationship between Intermolecular Interactions and Solid-State Photophysical Properties of Organic Co-Crystals

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