Nano-sized I12L6 Molecular Capsules Based on the [N⋅⋅⋅I+⋅⋅⋅N] Halogen Bond

Turunen, Lotta; Warzok, Ulrike; Schalley, Christoph A.; Rissanen, Kari

doi:10.1016/j.chempr.2017.08.010

Cited by 95 publications

(117 citation statements)

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“…ESI-MS measurements supported the selective formation of the halogen-bonded capsules with twelve [NÁ Á ÁIÁ Á ÁN] + bonds. 46 The structures of the [NÁ Á ÁIÁ Á ÁN] + halogen-bonded dimeric and hexameric capsules were further confirmed and studied by a combination of ESI-MS, DT-IMS and theoretical calculations. 17 Rearrangement of the hexameric into pentameric capsules upon changing the solvent from chloroform to dichloromethane was observed.…”

Section: Applications In Supramolecular Chemistrymentioning

confidence: 89%

“…Only of late has the three-center [DÁ Á ÁXÁ Á ÁD] + halogen bond been introduced as a supramolecular synthon in selfassemblies. 17,[45][46][47] Multiple [NÁ Á ÁIÁ Á ÁN] + halogen bonds were used in the formation of dimeric capsules from ethylene-bridged tetrakis-(3-pyridyl)cavitands (Fig. 16).…”

Section: Applications In Supramolecular Chemistrymentioning

confidence: 99%

“…Ethylenebridged tetrakis(pyridyl)cavitands were found to provide a suitable core structure to adjust the position of the electron donor, D, in the way that the construction of capsular assemblies with different geometries and sizes could be achieved. 46 By changing the position of the pyridyl N-atoms of the ethylenebridged cavitands from meta to para (Fig. 16), [NÁ Á ÁIÁ Á ÁN] + halogen-bonded octahedral hexameric capsules could be constructed.…”

Section: Applications In Supramolecular Chemistrymentioning

confidence: 99%

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Halogen bonds of halonium ions

2020

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Section: Applications In Supramolecular Chemistrymentioning

confidence: 89%

Section: Applications In Supramolecular Chemistrymentioning

confidence: 99%

Section: Applications In Supramolecular Chemistrymentioning

confidence: 99%

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Halogen bonds of halonium ions

2020

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“…The synthesis of [N−I−N] + complexes by Ag I cation exchange reaction has enabled construction of complex halonium ion‐based supramolecular structures . The results by Erdélyi et al.…”

Section: Introductionmentioning

confidence: 99%

Strong N−X⋅⋅⋅O−N Halogen Bonds: A Comprehensive Study on N‐Halosaccharin Pyridine N‐Oxide Complexes

2019

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A study of the strong N−X⋅⋅⋅−O−N+ (X=I, Br) halogen bonding interactions reports 2×27 donor×acceptor complexes of N‐halosaccharins and pyridine N‐oxides (PyNO). DFT calculations were used to investigate the X⋅⋅⋅O halogen bond (XB) interaction energies in 54 complexes. A simplified computationally fast electrostatic model was developed for predicting the X⋅⋅⋅O XBs. The XB interaction energies vary from −47.5 to −120.3 kJ mol−1; the strongest N−I⋅⋅⋅−O−N+ XBs approaching those of 3‐center‐4‐electron [N−I−N]+ halogen‐bonded systems (ca. 160 kJ mol−1). 1H NMR association constants (KXB) determined in CDCl3 and [D6]acetone vary from 2.0×100 to >108 m−1 and correlate well with the calculated donor×acceptor complexation enthalpies found between −38.4 and −77.5 kJ mol−1. In X‐ray crystal structures, the N‐iodosaccharin‐PyNO complexes manifest short interaction ratios (RXB) between 0.65–0.67 for the N−I⋅⋅⋅−O−N+ halogen bond.

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“…Controlling of chemical reactions by non-covalent or weak interactions are gaining significant interests.T om ake newer or functional materials on demanda ppropriate interactions like halogenb onding, [30] charge-transfer, [31] hydrophobic effect, [32] cation-p, [33] anion-p, [34] etc. are generallyu sed routinely.…”

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confidence: 99%

Unsymmetrical Disulfides Synthesis via Sulfenium Ion

Parida

Choudhuri

Mal

2019

Chemistry An Asian Journal

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An umpolunga pproachf or the synthesis of unsymmetrical disulfides via sulfenium ion is reported.I ns itu generated electrophilic sulfeniumi on from electron-rich thiols reacted with second thiols to yield unsymmetrical disulfides. Using an iodine catalysta nd 4-dimethylaminopyridine (DMAP)/water as promoter,t he target syntheses were achieved in one pot under aerobic condition.Organicd isulfides are important functional moieties found in variousm arine natural products, [1] pharmaceuticals, [2] materials [3] and polymers. [4] Disulfides are also known for their odors especially in kitchen items, like in onions and garlics. [5] Pharmaceutically active disulfides are known to have anti-inflammatory, [6] antitumour, [7] antioxidants [8] and antiulcer [9] activities. Chemically,o rgano-disulfides are being used in catalyst, [10] in ligand designing, [11] towards producing fine chemicals andi n functional group protections. [12] In addition, the concept of constitutional dynamic chemistry (CDC) [13] and dynamic combinatorial chemistry (DCC) [14] is documented using the chemistry of disulfides. Due to the reversibility nature of the disulfide bond, formation of many products could be possible when more than one thiol building blocks present in equilibrium. [15] Therefore, it's always challengingt os ynthesize selectively any unsymmetrical disulfides from mixtureo ft hiols in one pot. [16] In Figure 1a,f ew examples of either pharmaceutically important or naturallyo ccurring molecules containing disulfides functionalities are shown. [16b] The known approaches for the synthesis of disulfides are mainly based on using molecular oxygen, [17] transition metals, [18] phosphine-free cationic rhodium(I) complex catalyst, [19] Cu I -phenanthroline catalyst, [20] base catalyzed, [21] non-transition metals, [22] oxidants, [23] sodium perborate, [24] metal organicf rame works (MOFs), [25] microwavea ssisted, [26] electrochemical methods, [27] etc. Recently Dethe and co-workersd eveloped synthesis of unsymmetrical disulfides using fac-Ir(ppy) 3 as photocatalyst and visible light from white LED (Figure 1b). [28] Similarly,u nsymmetrical disulfide synthesis is also reported using O 2 as the oxidant and cobalt(II)phthalocyanine-tetra-sodium sulfonate as the catalyst (Figure 1b). [29] Herein, we reporto ne pot synthesis of unsymmetrical organodisulfides ( Figure 1c)v ia umpolung approach in ethanol sol-

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Nano-sized I12L6 Molecular Capsules Based on the [N⋅⋅⋅I+⋅⋅⋅N] Halogen Bond

Cited by 95 publications

References 47 publications

Halogen bonds of halonium ions

Halogen bonds of halonium ions

Strong N−X⋅⋅⋅O−N Halogen Bonds: A Comprehensive Study on N‐Halosaccharin Pyridine N‐Oxide Complexes

Unsymmetrical Disulfides Synthesis via Sulfenium Ion

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