Tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation

Verboom, Willem; Datta, Sumana; Asfari, Zouhair; Harkema, Sybolt; Reinhoudt, David N.

doi:10.1021/jo00046a021

Cited by 122 publications

(61 citation statements)

References 5 publications

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“…[37] & [24] Li/Br exchange on 3 with an excess amount of t-BuLi gives intermediate tetrakis(aryllithium), which is reacted with Nmethylformanilide, to provide tetraaldehyde 4. [38] An analogous procedure, in which the t-BuLi is replaced with n-BuLi (2 equiv), [24] gives dialdehyde 5.…”

Section: Synthesismentioning

confidence: 99%

“…Prior to use, benzaldehyde and p-anisaldehyde were subjected to the general method for purifi cation of aldehydes. [55] 5,11,17,23-Tetrabromo-25,26,27,28-tetrakis(methoxyethoxy)calix [4]arene (3) in the locked 1,3-alternate conformation [37] was prepared using previously reported procedures. [24] 2,3-Bis(hydroxyamino)-2,3-dimethylbutane was obtained by reduction of the corresponding dinitro compound using Al/Hg.…”

Section: Materials and Special Proceduresmentioning

confidence: 99%

See 1 more Smart Citation

1,3-Alternate calix[4]arene nitronyl nitroxide tetraradical and diradical: synthesis, X-ray crystallography, paramagnetic NMR spectroscopy, EPR spectroscopy, and magnetic studies

et al. 2007

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Section: Synthesismentioning

confidence: 99%

Section: Materials and Special Proceduresmentioning

confidence: 99%

1,3-Alternate calix[4]arene nitronyl nitroxide tetraradical and diradical: synthesis, X-ray crystallography, paramagnetic NMR spectroscopy, EPR spectroscopy, and magnetic studies

et al. 2007

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“…For column chromatography, silica gel 60 (Sorbent Technologies, 200-425 mesh) was used. Parent tetrahydroxycalix [4]arene [31] and calixarene 14 b [32] were prepared according to the published procedures. NO 2 /N 2 O 4 was generated from copper and concentrated HNO 3 .…”

Section: Discussionmentioning

confidence: 99%

Long Synthetic Nanotubes from Calix[4]arenes

Organo

Sgarlata

Firouzbakht

et al. 2007

Chemistry A European J

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We report the synthesis and encapsulation properties of long (up to 5 nm) molecular nanotubes 1-4, which are based on calix[4]arenes and can be filled with multiple nitrosonium (NO(+)) ions upon reaction with NO(2)/N(2)O(4) gases. These are among the largest nanoscale molecular containers prepared to date and can entrap up to five guests. The structure and properties of tubular complexes 1(NO(+))(2)-4(NO(+))(5) were studied by UV/Vis, FTIR, and (1)H NMR spectroscopy in solution, and also by molecular modeling. Entrapment of NO(+) in 1(NO(+))(2)-4(NO(+))(5) is reversible, and addition of [18]crown-6 quickly recovers starting tubes 1-4. The FTIR and titration data revealed enhanced binding of NO(+) in longer tubes, which may be due to cooperativity. The described nanotubes may serve as materials for storing and converting NO(x) and also offer a promise to further develop supramolecular chemistry of molecular containers. These findings also open wider perspectives towards applications of synthetic nanotubes as alternatives to carbon nanotubes.

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“…Из литературы известно, что взаимодействие (тиа)каликсаренов с галоидными алкилами приводит к образованию тетразамещенных продуктов в стереоизомерной форме 1,3-альтернат в присутствии катиона цезия. [22,23] При взаимодействии диаллилового эфира п-трет-бутилкаликс[4]арена 4 наблюдается образование смеси двух стереоизомеров: 1,3-альтернат 8а и частичный конус 8б, которая была разделена дробной кристаллиза-цией. Выходы бифункциональных производных трет-бутилкаликс [4]арена составили 56 и 24 %, соответ-ственно (Таблица 1).…”

Section: результаты и обсуждениеunclassified