Halogen bonding in 5-iodo-1-arylpyrazoles investigated in the solid state and predicted by solution<sup>13</sup>C-NMR spectroscopy

Popa, Marcel Mirel; Man, Isabela Costinela; Drăghici, Constantin; Shova, Sergiu; Caira, Mino R.; Dumitraşcu, Florea; Dumitrescu, Dan

doi:10.1039/c9ce01263j

Cited by 18 publications

(33 citation statements)

References 71 publications

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“…In 2019, Dumitrascu and co‐workers designed series of self‐complementary 5‐Iodo‐1‐arylpyrazole derivatives ( IPz‐1 , IPz‐2 and IPz‐3 ) (Figure 21A) modified by different substitutions on the aryl group attached at the 1‐position of the pyrazole ring for driving the supramolecular assembly through three types of halogen bonding, namely C−I⋅⋅⋅N, C−I⋅⋅⋅O and C−I⋅⋅⋅π [102] . In IPz‐1 , the primary interaction in the crystal packing was strong I⋅⋅⋅N XB contacts (with interatomic distance 2.7–3.4 Å) that lead to extended chain formation, while 2D assembly via interchain interaction were driven by CH⋅⋅⋅O HBs.…”

Section: Halogen Bonded Supramolecular Polymers and Materialsmentioning

confidence: 99%

Recent Developments in Polymeric Assemblies and Functional Materials by Halogen Bonding

Biswas

Das

2021

ChemNanoMat

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Polymers have long been known to us for their versatile utility in our daily lives. With many years of successful advancement in controlled polymer synthesis and supramolecular chemistry, currently an amalgamation of these two fields is becoming increasingly important for generating modern‐day emerging polymeric materials. Hydrogen bonding and other noncovalent interactions like π‐stacking, host‐guest interaction, electrostatic interaction, metal‐ligand coordination have been explored much to this context, unlike the recently emerged halogen bonding, which indeed shows advantageous features like superior hydrophobicity, directionality and polar solvent resistance compared to ubiquitous hydrogen bonding. Hence, rendering these properties of halogen bonding into polymeric domain for generating functional materials for application in advance nanotechnologies is highly desirable. In the recent years, substantial progress has been made in fulfilling this challenging goal. This is evident from the escalating number of scientific publications in this research area every year. In this minireview, we have summarized the most recent developments in the field of halogen bonded polymeric assemblies and supramolecular polymers and discussed them in the context of their emerging materials properties and functions. Emphasis is given on highlighting various design criteria adopted in crystal engineering, covalent and supramolecular polymers in the past five years for constructing diverse organic functional materials, viz. liquid crystals, photoresponsive and photochromic materials, biomaterials and gels, self‐healing materials and many others by virtue of this highly directional supramolecular tool. In conclusion, a brief perspective on the advantages, challenges and future prospects in this rapidly growing field of research is discussed.

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Section: Halogen Bonded Supramolecular Polymers and Materialsmentioning

confidence: 99%

Recent Developments in Polymeric Assemblies and Functional Materials by Halogen Bonding

Biswas

Das

2021

ChemNanoMat

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“…The We recently discovered that halogenated sydnones [44,45] and pyrazoles [46] are molecules with high potential for investigating the propensity of halogen bonding and its contribution among the other intermolecular interactions. We reported three types of halogen bonding in our investigations, all involving the iodine atom: I• • • N, I• • • O and I• • • π [46]. During our investigation, we also showed, with examples from the Cambridge Structural Database (CSD), that halogen interactions are important intermolecular forces which can either stabilize or even direct the crystalline network.…”

Section: X-ray Diffraction Analysismentioning

confidence: 99%

“…More particularly, halogen-oxygen, halogen-nitrogen or halogen-π (Figure 1c) interactions were reported both in liquid and solid state. We recently discovered that halogenated sydnones [44,45] and pyrazoles [46] are molecules with high potential for investigating the propensity of halogen bonding and its contribution among the other intermolecular interactions. We reported three types of halogen bonding in our investigations, all involving the iodine atom: I⋯N, I⋯O and I⋯π [46].…”

Section: Introductionmentioning

confidence: 99%

5-Iodo-1-Arylpyrazoles as Potential Benchmarks for Investigating the Tuning of the Halogen Bonding

et al. 2020

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5-Iodo-1-arylpyrazoles are interesting templates for investigating the halogen bond propensity in small molecules other than the already well-known halogenated molecules such as tetrafluorodiiodobenzene. Herein, we present six compounds with different substitution on the aryl ring attached at position 1 of the pyrazoles and investigate them in the solid state in order to elucidate the halogen bonding significance to the crystallographic landscape of such molecules. The substituents on the aryl ring are generally combinations of halogen atoms (Br, Cl) and various alkyl groups. Observed halogen bonding types spanned by these six 5-iodopyrazoles included a wide variety, namely, C–I⋯O, C–I⋯π, C–I⋯Br, C–I⋯N and C–Br⋯O interactions. By single crystal X-ray diffraction analysis combined with the descriptive Hirshfeld analysis, we discuss the role and influence of the halogen bonds among the intermolecular interactions.

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“…We have investigated recently the propensity of halogen bonding in halogenated 1-arylpyrazoles and we found them as versatile structures for study of this interesting interaction. 54…”

Section: Synthesis and Characterization Of The 1-arylpyrazoles 6a-gmentioning

confidence: 99%

Introducing chirality in halogenated 3-arylsydnones and their corresponding 1-arylpyrazoles obtained by 1,3-dipolar cycloaddition

et al. 2020

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Halogen bonding in 5-iodo-1-arylpyrazoles investigated in the solid state and predicted by solution¹³C-NMR spectroscopy

Abstract: Halogen bonding as important directional forces in the supramolecular structure of iodinated 1-arylpyrazoles.

Cited by 18 publications

References 71 publications

Recent Developments in Polymeric Assemblies and Functional Materials by Halogen Bonding

Recent Developments in Polymeric Assemblies and Functional Materials by Halogen Bonding

5-Iodo-1-Arylpyrazoles as Potential Benchmarks for Investigating the Tuning of the Halogen Bonding

Introducing chirality in halogenated 3-arylsydnones and their corresponding 1-arylpyrazoles obtained by 1,3-dipolar cycloaddition

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Halogen bonding in 5-iodo-1-arylpyrazoles investigated in the solid state and predicted by solution13C-NMR spectroscopy

Abstract: Halogen bonding as important directional forces in the supramolecular structure of iodinated 1-arylpyrazoles.

Cited by 18 publications

References 71 publications

Recent Developments in Polymeric Assemblies and Functional Materials by Halogen Bonding

Recent Developments in Polymeric Assemblies and Functional Materials by Halogen Bonding

5-Iodo-1-Arylpyrazoles as Potential Benchmarks for Investigating the Tuning of the Halogen Bonding

Introducing chirality in halogenated 3-arylsydnones and their corresponding 1-arylpyrazoles obtained by 1,3-dipolar cycloaddition

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Product

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Halogen bonding in 5-iodo-1-arylpyrazoles investigated in the solid state and predicted by solution¹³C-NMR spectroscopy