Synthesis of Dihomocalix[4]naphthalenes:  First Members of a New Class of [1.2.1.2](1,3)Naphthalenophanes

Georghiou, Paris E.; Li, Zhaopeng; Ashram, Muhammad; Miller, David O.

doi:10.1021/jo9520654

Cited by 19 publications

(21 citation statements)

References 10 publications

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“…35 In solution, these molecules are conformationally flexible, as evidenced by their 1 H NMR spectra. In the solid state, an X-ray structure showed 48 to be in a 1,2-alternate conformation, with each of the pairs of the methylene-bridged naphthyl groups being anti to each other.…”

Section: Dihomocalix[4]naphthalenesmentioning

confidence: 99%

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Calixnaphthalenes: Deep, Electron-Rich Naphthalene Ring-Containing Calixarenes. The First Decade.

Georghiou¹,

Li²,

Ashram³

et al. 2005

Synlett

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This Account is dedicated to Professor George Just (McGill University) and to the memory of the late Professors Guido Perold (University of the Witwatersrand) and Satoru Masamune (University of Alberta and M.I.T.) for giving me the initial opportunities to undertake research in chemistry under their guidance; and also to Janette, Melissa, Andreas, Noulla and Menelaos. SYNLETT 2005, No. 6, pp 0879-08910 6 . 0 4 . 2 0 0 5 Advanced online publication: 23.03.2005Abstract: The first naphthalene ring-based analogues of the betterknown and extensively studied calixarenes were synthesized in 1993. Since that time, our group has focused its research on the design and synthesis of other 'calixnaphthalenes'. These endeavours are motivated partly due to the synthetic challenges which they provide, and to the challenges in deciphering their structural and complexation properties. Calixnaphthalenes offer several advantages over their calixarene analogues. Among these are the facts that they can form deeper, more electron-rich and in some cases, chiral, cavities. They also provide a wide range of potential new scaffolds upon which to design and build new receptors for neutral, or charged guest species. Their supramolecular complexation properties have barely been explored as yet since in most cases, only relatively small quantities only of these compounds have been obtained. In this review, all of the known, and previously unreported calixnaphthalenes are described. As well, some of the compounds, which are described, are still subjects of ongoing research.

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Section: Dihomocalix[4]naphthalenesmentioning

confidence: 99%

“…Tetrahomodithia compounds 50 and 51 formed crystalline complexes with Ag + but none of their other complexation properties were studied in any detail ( Figure 16). 35 …”

Section: Dihomocalix[4]naphthalenesmentioning

confidence: 99%

Calixnaphthalenes: Deep, Electron-Rich Naphthalene Ring-Containing Calixarenes. The First Decade.

Georghiou¹,

Li²,

Ashram³

et al. 2005

Synlett

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“…Biologically significant guests such as amino acids 21 have also been shown to form complexes in aqueous solutions; in the case of these guests, aliphatic CH-π interactions were shown to be the major factor in determining binding, while in the case of aromatic amino acids, the major factor was π-π interactions. A cyclic tetrameric structure has also been claimed for the condensation product of 4-amino [5]hydroxynaphthalene-2,7-disulfonic acid with formaldehyde, 27 and this product ( Figure 5.7a) has been shown to form complexes with polycyclic aromatic compounds in water, with complex strength increasing with the number of rings in the guest. Other macrocyclic ring compounds have also been shown to form complexes with cyclotetrachromotropylene.…”

Section: Calixnaphthalenesmentioning

confidence: 85%

“…However, there are four possible isomers, as shown in Figure 5.2. A different series of macrocycles were synthesised, again using a stepwise process rather than a simple condensation, to give dihomocalix [4]naphthalenes, 5 the structures of which are shown in Figure 5.3a, with the methoxy groups inside the macrocycle. Further analysis showed the isomers were all conformationally mobile, although substitution to give the benzoate esters restricted this.…”

Section: Calixnaphthalenesmentioning

confidence: 99%

“…2 Much of the work up to 2005 on calixnaphthalenes has been reviewed by Georghiou et al . Both these materials were again shown to be conformationally flexible in solution 5 and a cone-like structure was not adopted. 4 These structures show one major difference from the classic calixarenes, in that the -OH groups are positioned on the 'outside' of the macrocycle (similar to the resorcinarenes) rather than 'inside' the main ring.…”

Section: Calixnaphthalenesmentioning

confidence: 99%

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Heterocalixarenes and Calixnaphthalenes

Davis

Higson

2011

Macrocycles

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Homothiacalix[4]arenes: Synthetic Exploration and Solid‐State Structures

Thomas¹,

Hecke²,

Robeyns³

et al. 2011

Chemistry A European J

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Homothiacalix[n]arenes have been largely underexposed compared with related (homo)heteracalixarenes, although their inherent structural features are particularly attractive for supramolecular host-guest chemistry. In this contribution, the synthetic macrocyclization protocols that afford homothiacalix[n]arenes have been reinvestigated and optimized, providing straightforward access to the parent homothiacalix[4]arene skeleton. Moreover, inner-rim (bis and tetrakis) ester functionalization and dimethylenethia bridge oxidation were successfully performed as well. Solution-phase (variable-temperature) NMR spectroscopy studies and solid-state X-ray structures provided complementary information on the conformational features of the novel macrocycles.

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Synthesis of Dihomocalix[4]naphthalenes: First Members of a New Class of [1.2.1.2](1,3)Naphthalenophanes

Cited by 19 publications

References 10 publications

Calixnaphthalenes: Deep, Electron-Rich Naphthalene Ring-Containing Calixarenes. The First Decade.

Calixnaphthalenes: Deep, Electron-Rich Naphthalene Ring-Containing Calixarenes. The First Decade.

Heterocalixarenes and Calixnaphthalenes

Homothiacalix[4]arenes: Synthetic Exploration and Solid‐State Structures

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