1,2,4,5-Tetravinylbenzene

Schrievers, Theodor; Brinker, Udo H.

doi:10.1055/s-1988-27561

Cited by 12 publications

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“…Although molecules with two, three or even four azide groups at one C atom are now available (Nishiyama & Yamaguchi, 1988;Nishiyama et al, 1987;Petrie et al, 1997;Lyssenko et al, 2005), a survey of the Cambridge Structural Database (Allen, 2002) revealed the absence of X-ray diffraction structures of benzene derivatives with geminal diazide groups. The photobromination of 1,2,4,5-tetramethylbenzene, (I), afforded 1,2,4,5-tetrakis(dibromomethyl)benzene, (II), in 90% yield (Soyer et al, 1975;Schrievers & Brinker, 1988). Compound (II) reacts with NaN 3 to give 1,2,4,5-tetrakis(diazidomethyl)benzene, (III), in 91% yield (Gilbert, 1987).…”

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1,2,4,5-Tetrakis(diazidomethyl)benzene

Wieland

Wagner

et al. 2009

Acta Crystallogr C

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The molecule of the title compound, C(10)H(6)N(24), lies on a crystallographic inversion centre located in the middle of the benzene ring. Steric overcrowding by the bulky N(3) groups is avoided by the tendency of four azide entities to be arranged parallel to the benzene ring and the other four azide groups to be arranged alternately above and below the benzene plane in a skeletal C(i) symmetry. The compound is of interest for high-energy research and as a precursor for the synthesis of carbon nanotubes, nanospheres or high-nitrogen carbon nitrides with great potential for biological and technological applications.

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Section: Commentmentioning

confidence: 99%

1,2,4,5-Tetrakis(diazidomethyl)benzene

Wieland

Wagner

et al. 2009

Acta Crystallogr C

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Supramolecular Ladders from Dimeric Cucurbit[6]uril

2013

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Supramolecular Ladders from Dimeric Cucurbit[6]uril

2013

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The cucurbit[n]uril (CB[n]; n = 5, 6, 7, 8, 10) family [1] of molecular containers have become the object of intense focus in the field of supramolecular chemistry over the past decade. [2] This surge in interest is due to the ability of CB [n] compounds to bind to suitable cationic guests with both high affinity (K a up to 10 15 m À1 ) and high selectivity in water [3] and the stimuli responsiveness (e.g. pH, chemical, photochemical, electrochemical) of the corresponding CB[n]·guest complexes. The remarkable recognition properties of CB[n]·guest complexes have been used as the basis for numerous applications of CB[n] compounds including chemical-sensing ensembles, [4] membrane-protein fishing, [5] drug solubilization and delivery, [6] and supramolecular catalysis. [7] Of highest utility for the construction of functional CB[n] derived systems is the ability of CB[8] to form CB[8]·guest 2 ternary complexes-generally with heteropairs of electron-deficient and electron-rich aromatic guests-which has been exploited by the Kim, Urbach, Scherman, and Brunsveld research groups to construct molecular machines, sensing systems, promotors of protein dimerization, and complex macromolecular and nanoparticle architectures. [8] Over the years, our research group has investigated the related ability of CB[10] and bis-ns-CB[10] to form ternary complexes that perform biomimetic functions (e.g. homotropic allostery, metalloporphyrin sensing) or form supramolecular polymers. [1e, 9] Recently, we and others have developed routes to prepare monofunctionalized derivatives of CB[6] [10] and CB [7]. [11] We envisioned that it would be possible to adapt this chemistry toward the construction of CB[n] dimers containing two covalently connected, fully formed CB[n] groups. Because each CB[n] cavity of such CB[n] dimers would separately retain the ability to bind to a wide array of guests with high affinity and selectivity, we surmised that dimeric CB[n] would extend the range of appropriate (hetero) guest pairs and thereby complement the use of CB[8] in biomolecular derivatization and dimerization events, the formation of supramolecular polymers, and the assembly of nanoscale systems. Herein, we demonstrate the synthesis of dimeric CB[6] compounds 1 and 2 and the ability of 1 to form supramolecular ladders [12] when combined with oligomeric viologen-containing guests. Scheme 1. a) Synthesis of CB[6] dimers 1 and 2, and b) structures of guests 6-14, and c) guests 15-18.

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1,2,4,5-Tetravinylbenzene

Cited by 12 publications

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1,2,4,5-Tetrakis(diazidomethyl)benzene

1,2,4,5-Tetrakis(diazidomethyl)benzene

Supramolecular Ladders from Dimeric Cucurbit[6]uril

Supramolecular Ladders from Dimeric Cucurbit[6]uril

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