Wheel-and-axle topology-driven halogen bonds: formation of ladder, 1D and 2D networks in hexa-coordinated Sn(<scp>iv</scp>) porphyrins

Rani, Jyoti; Kaur, Gurkiran; Sushila,; Diksha, .; Yadav, Rashmi; Kataria, Ramesh; Venugopalan, Paloth; Natarajan, Palani; Chaudhary, Arvind; Patra, Ranjan

doi:10.1039/c8ce01877d

Cited by 15 publications

(26 citation statements)

References 40 publications

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“…A subsequent analysis indicated that only 3 structures (11% of the data set) exhibit type I interactions, while 17 structures (63% of the data set) exhibit type II interactions. Notably, 1 porphyrin structure (CSD code KIWTIW; Figure a) was found to exhibit both type I and type II interactions, straddling both sets. The geometry of the I···I motifs in the remaining 8 structures could not be interpreted as representing either type I or type II interactions; consequently, these were classified as contacts (Figure S10 and Table S13).…”

Section: Resultsmentioning

confidence: 99%

Database Investigation of Halogen Bonding and Halogen···Halogen Interactions between Porphyrins: Emergence of Robust Supramolecular Motifs and Frameworks

Spilfogel

Titi

Friščić

2021

Crystal Growth & Design

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We provide a Cambridge Structural Database (CSD) analysis of the role of halogen bonds and halogen···halogen interactions in the solid-state structures of porphyrins. This survey provides a detailed view of halogens in porphyrin self-assembly, highlighting interaction motifs beyond the often considered iodine-based halogen bonds. Particularly notable are the observations of self-assembly through β-positioned substituents, the role of the pyrrole π-system as a halogen bond acceptor, and an abundance of chlorine-based halogen···halogen and halogen-bonding motifs. This overview enabled the observation and systematic classification of complex, multipoint recognition motifs in halogen-based architectures. Similarly to synthons in hydrogen-bonded crystal engineering, these motifs appear in discrete molecular assemblies and can also underlie the formation of two- and three-dimensional frameworks. The systematic categorization of these robust motifs provides a foundation for the design of complex halogen-based supramolecular architectures.

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Section: Resultsmentioning

confidence: 99%

Database Investigation of Halogen Bonding and Halogen···Halogen Interactions between Porphyrins: Emergence of Robust Supramolecular Motifs and Frameworks

Spilfogel

Titi

Friščić

2021

Crystal Growth & Design

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“…In our previous work on six coordinated tin-porphyrin complexes, [29][30][31] we observed an interesting phenomenon in the solid phase. The location of the halogen bond donor or acceptor on the porphyrin plays a critical role in the self-assembly process.…”

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confidence: 89%

“…44,45 Similarly, replacing I-atoms with Br-atoms at the axial linkers led for the formation of type I XB interactions. 30 From these two examples it is clear that axial halogen atoms are either reluctant to participate in XB interactions altogether or participate in type I XB interactions due to a decrease in the potential of the σ-hole. Type I XB interactions are not truly considered an attractive contact (two electropositive regions of halogens (δ+) are in short contact and can form due to crystal packing), whereas type II is more attractive in nature (the electropositive region (δ+) of one halogen is in direct contact with electronegative region (δ-) of the other which provides a stabilizing electrostatic interaction).…”

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confidence: 99%

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Porphyrin’s Ring Current as a Driving Force for Halogen Bond Interactions: A Computational Study

Rani¹,

Patra³

2019

Preprint

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“…Apart from the usual halogen bonding such as I⋅⋅⋅O, I⋅⋅⋅N, I⋅⋅⋅π and I⋅⋅⋅I, rare I⋅⋅⋅S bonds were also found for the first time. This idea was further explored in metalloporphyrin complexes by Patra and co‐workers through a ‘wheel and axle’ model comprising of a series of Sn(axial‐L) 2 −(5,10,15,20‐tetraiodoporphyrin) Sn IV TIPP(L) 2 , where L= halogen/nitro‐substituted benzoate moiety] derivatives (Figure 23C) [113] . In this design, the wheel comprised of the porphyrin unit, with the meso ‐phenyl position occupied by two pairs of iodine atoms.…”

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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Wheel-and-axle topology-driven halogen bonds: formation of ladder, 1D and 2D networks in hexa-coordinated Sn(iv) porphyrins

Abstract: Wheel-and-axle topology-driven halogen bonded supramolecular networks in six-coordinated Sn(iv)-porphyrins.

Cited by 15 publications

References 40 publications

Database Investigation of Halogen Bonding and Halogen···Halogen Interactions between Porphyrins: Emergence of Robust Supramolecular Motifs and Frameworks

Database Investigation of Halogen Bonding and Halogen···Halogen Interactions between Porphyrins: Emergence of Robust Supramolecular Motifs and Frameworks

Porphyrin’s Ring Current as a Driving Force for Halogen Bond Interactions: A Computational Study

Recent Developments in Polymeric Assemblies and Functional Materials by Halogen Bonding

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