The Modular Approach in Supramolecular Chemistry

Higler, Irene; Timmerman, Peter; Verboom, Willem; Reinhoudt, David N.

doi:10.1002/(sici)1099-0690(199812)1998:12<2689::aid-ejoc2689>3.0.co;2-9

Cited by 47 publications

(1 citation statement)

References 165 publications

(15 reference statements)

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“…[18,19] Depending on the connecting site, there are three possible modes of assembly for these double calix [4]arenes: head-to-head, tail-to-tail, or head-to-tail. Or, put another way, by both larger (upper) rims, by both smaller (lower) rims, or by the larger (upper) rim of one and the smaller (lower) rim of another, respectively.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of Bis(calix[4]arenes), Bis(crown ether)-Substituted Calix[4]arenes, Aza-Crown Calix[4]arenes, and Thiaza-Crown Calix[4]arenes

2000

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The easy transformation of 5,11,17,23-tetra-tert-butyl-25,27bis(aminoethoxy)-26,28-dihydroxycalix[4]arene(2) into 5, 11,17,23-tetra-tert-butyl-26,28-dihydroxy-25,27-bis(2-isothiocyanoethoxy)calix[4]arene (3) and 5,11,17,23-tetra-tertbutyl-25,27-bis(chloroacetamidoethoxy)-26,28-dihydroxycalix[4]arene (4) has been exploited for the development of an efficient and expeditious synthesis of a variety of calix[4]3587 calix[4]arenes]. The functionality of compounds 2 and 3 allowed the formation of intramolecular bridges, leading to capped calix[4]arenes (compounds 5, 10, and 14) as well as to the construction of double calix[4]arene units by means of spacers containing thiourea or amide-sulfur groups (compounds 6 and 15, respectively). In addition, the bis(isothiocyanate) derivative 3 gave access to a high-yield preparation of heteroditopic bis(crown ether) calix[4]arenes (7−9) from commercial amino crown ethers.

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Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of Bis(calix[4]arenes), Bis(crown ether)-Substituted Calix[4]arenes, Aza-Crown Calix[4]arenes, and Thiaza-Crown Calix[4]arenes

2000

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Synthesis of (Hemi)Carceplex Adsorbates for Self-Assembly on Gold

et al. 2000

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The synthesis of sulfide‐functionalized (hemi)carceplexes suitable for self‐assembly on gold is described. A noncentrosymmetrical carceplex 9 (guest DMF) was synthesized by the combination of calix[4]arene 4 and resorcin[4]arene 3, while a noncentrosymmetrical hemicarceplex 12 (guest NMP) was prepared by the combination of two different resorcin[4]arenes, 3 and 10. These adsorbates form ordered self‐assembled monolayers on gold with their quasi C4v axis perpendicular to the surface. The two positions possible for the incarcerated guest lead to diastereotopic surfaces.

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Stable Heterotopic Noncovalent Resorcin[4]arene Assemblies

Higler¹,

Grave²,

Breuning³

et al. 2000

Eur. J. Org. Chem.

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Resorcin[4]arene tetracarboxylic acids 5,6 (A) and resorcin[4]arene tetrapyridines 2,3 (P) self‐assemble in chloroform solution to form stable heterotopic AP dimers. Data from NMR titration and dilution experiments, as well as from vapor‐pressure osmometry (VPO), indicate that the AP dimer is formed with an association constant greater than 107 M−1. Solid‐solution extraction experiments are indicative of the formation of a 2:1 trimer (A2P), while self‐associated homotopic species (A2 and A3) can be detected by NMR and VPO. Analysis of the heterotopic noncovalent assembly process over a range of compositions shows that these other species are much less stable than the AP heterodimer, which is the exclusive species at an A/P concentration ratio of 1:1 (> 99.7% of the total at 10 mM).

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The Modular Approach in Supramolecular Chemistry

Abstract: This review describes covalent and non‐covalent combinations of building blocks, e.g. calix[4]arenes, resorcin[4]arenes, cyclodextrins, porphyrins, and cyclotriveratrylenes, leading to well‐defined large (receptor) molecules.

Cited by 47 publications

References 165 publications

An Efficient Synthesis of Bis(calix[4]arenes), Bis(crown ether)-Substituted Calix[4]arenes, Aza-Crown Calix[4]arenes, and Thiaza-Crown Calix[4]arenes

An Efficient Synthesis of Bis(calix[4]arenes), Bis(crown ether)-Substituted Calix[4]arenes, Aza-Crown Calix[4]arenes, and Thiaza-Crown Calix[4]arenes

Synthesis of (Hemi)Carceplex Adsorbates for Self-Assembly on Gold

Stable Heterotopic Noncovalent Resorcin[4]arene Assemblies

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