Bamboo-like Chained Cavities and Other Halogen-Bonded Complexes from Tetrahaloethynyl Cavitands with Simple Ditopic Halogen Bond Acceptors

Turunen, Lotta; Pan, Fangfang; Beyeh, Ngong Kodiah; Trant, John F.; Ras, Robin H. A.; Rissanen, Kari

doi:10.1021/acs.cgd.7b01517

Cited by 17 publications

(14 citation statements)

References 62 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, haloarenes are known to be effective in this kind of strengthening . Halogen bonding has been studied widely with cavitands and in macromolecular systems . With the cavitands, focus in halogen bonding has been among forming capsules, networks, and ribbons .…”

Section: Methodsmentioning

confidence: 99%

“…Halogen bonding has been studied widely with cavitands and in macromolecular systems . With the cavitands, focus in halogen bonding has been among forming capsules, networks, and ribbons . Polymers, on the other hand, have been studied with small molecules and macromolecules yielding materials with added functionality as well as controlled morphology and orientation .…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Halogen‐Bond‐Mediated Self‐Assembly of Polymer–Resorcinarene Complexes

Välimäki

Gustavsson

Beyeh

et al. 2019

Macromol. Rapid Commun.

Self Cite

View full text Add to dashboard Cite

A new supramolecular system based on halogen‐bonded macromolecular substances is presented. Binding and complex formation between a halogen bond acceptor N‐benzyl ammonium resorcinarene bromide and a library of polymeric halogen bond donors based on iodotetrafluorophenoxy functionality is shown. The complex formation was confirmed in liquid state by dynamic light scattering and transmission electron microscopy. Spectroscopic measurements in the solid state verify the halogen bonding. In particular, the study shows that both homopolymers and polyethylene glycol block copolymers act as effective halogen bond donors leading to polymer‐architecture‐dependent complex morphologies.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Halogen‐Bond‐Mediated Self‐Assembly of Polymer–Resorcinarene Complexes

Välimäki

Gustavsson

Beyeh

et al. 2019

Macromol. Rapid Commun.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Rissanen and coworkers again demonstrated the tetrahaloethynyl cavitand as an ideal crown‐like conformational cavitand, suitable for building other highly ordered networks [39] . Crystallization of the tetrabromoethynyl cavitands form self‐included dimers with two of the bromoethynyl groups in the cavity of the adjacent cavitand, leaving six polarized halogen atoms available for XB interactions.…”

Section: Resorcinarene Cavitandsmentioning

confidence: 99%

Recent Advances in Halogen Bonded Assemblies with Resorcin[4]arenes

Twum

Beyeh

2020

The Chemical Record

Self Cite

View full text Add to dashboard Cite

Resorcinarenes are cavity‐containing compounds when in the crown conformation, from the calixarene family of concave compounds. These easy to synthesize macrocycles can be decorated at the upper rim through the eight hydroxyl groups and/or the 2‐position of the aromatic ring. They are good synthons in supramolecular chemistry leading to appealing assemblies such as open‐inclusion complexes, capsules and tubes through multiple weak interactions with various guests. Halogen bonding (XB) is a highly directional non‐covalent interaction by an electron‐deficient halogen atom as a donor that interacts with a Lewis base, the XB acceptor. This tutorial review provides an overview of recent advances in halogen‐bonded assemblies based on resorcinarenes and their derivatives, specifically focusing on discrete and capsular assemblies.

show abstract

“…[27,28] In the overwhelming majority of cases, fluorinated haloarenes [29][30][31][32][33] or haloalkanes [34][35][36] have been used as σ-hole donating partners of HaB toward nucleophilic azines. The structures of some co-crystals of azines with trinitrohalobenzenes, [37] haloacetylenes, [38][39][40] N-haloimides, [41] tetraiodoethylene, [42][43][44] iodoform, [45] which included X•••N HaBs, have been reported.…”

Section: Introductionmentioning

confidence: 99%

Azine Steric Hindrances Switch Halogen Bonding to N‐Arylation upon Interplay with σ‐Hole Donating Haloarenenitriles

Baykov

Geyl

Ivanov

et al. 2021

Chemistry An Asian Journal

View full text Add to dashboard Cite

An interplay between 4-bromo-and 4-iodo-5-nitrophthalonitriles (XNPN, X = Br or I) and any one of the azines (pyridine 1, 4-dimethylaminopyridine 2, isoquinoline 3, 4cyanopyridine 4, 2-methylpyridine 5, 2-aminopyridine 6, quinoline 7, 1-methylisoquinoline 8, and 2,2'-bipyridine 9) proceeds differently depending on steric and electronic effects of the heterocycles. Sterically unhindered azines 1-3 underwent N-arylation to give the corresponding azinium salts (characterized by 1 H and 13 C{H} NMR and high-resolution ESI-MS). In contrast, azines 4-9 with sterically hindered N atoms or bearing an electron-withdrawing substituent, form stable co-crystals with XNPN, where two interacting molecules are bound by halogen bonding. In all obtained cocrystals, X•••N structure-directed halogen bonds were recognized and theoretically evaluated including DFT calculations (PBE0-D3/def2-TZVP level of theory), QTAIM analysis, molecular electrostatic potential surfaces, and noncovalent interaction plot index. Estimated energies of halogen bonding vary from À 7.6 kcal/mol (for 6 • INPN) to À 11.4 kcal/mol (5 • INPN).

show abstract

Bamboo-like Chained Cavities and Other Halogen-Bonded Complexes from Tetrahaloethynyl Cavitands with Simple Ditopic Halogen Bond Acceptors

Abstract: Halogen-bonding provides a useful complement to hydrogen-bonding and metalcoordination as a tool for organizing supramolecular systems. Resorcinarenes, tetrameric bowl

Cited by 17 publications

References 62 publications

Halogen‐Bond‐Mediated Self‐Assembly of Polymer–Resorcinarene Complexes

Halogen‐Bond‐Mediated Self‐Assembly of Polymer–Resorcinarene Complexes

Recent Advances in Halogen Bonded Assemblies with Resorcin[4]arenes

Azine Steric Hindrances Switch Halogen Bonding to N‐Arylation upon Interplay with σ‐Hole Donating Haloarenenitriles

Contact Info

Product

Resources

About