Chemistry: analytical and immunological testing – Optical result
Patent
1998-03-20
2000-10-10
Warden, Jill
Chemistry: analytical and immunological testing
Optical result
549352, 549353, 525187, 522 8007, 522 8208, 436 74, 436 79, C07D32300, C07D40914, C08L 7102
Patent
active
061300969
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to chemical complexes in particular rotaxanes and pseudorotaxanes formed by addition of cationic cyclophanes and acyclic polyether derivatives, polyether derivatives useful in the preparation of such rotaxanes and pseudorotaxanes, uses of such rotaxanes and pseudorotaxanes and devices incorporating such rotaxanes and pseudorotaxanes.
There has been considerable recent interest concerning the control of molecular architectures in both the solid state and in solution. The known processes of molecular recognition and self-assembly have been employed to generate a number of topologically interesting and functioning supramolecular entities. One such known complex, a [2]pseudorotaxane (illustrated herein) is formed by interaction of two components, viz., an acyclic polyether derivative containing a .pi.-electron rich unit and an encircling .pi.-electron deficient cyclophane unit.
The purpose of the present invention is to provide by interaction of a cyclophane and an acyclic polyether derivative a novel rotaxane or pseudorotaxane complex which has unexpected novel and useful properties. Where reference is made hereafter to rotaxanes, including the claims, it should be taken to include reference to pseudorotaxanes also.
According to the present invention in a first aspect there is provided a rotaxane complex which is formed by interaction between an acyclic polyether derivative containing one or more .pi.-electron rich units and an encircling .pi.-electron deficient cyclophane unit, the acyclic polyether chain having terminal units inhibiting slippage of the cyclophane from the thread, at least one of the terminal units comprising a cation receptor unit.
The rotaxane complex of the first aspect is therefore formed by .pi.--.pi. interaction between two compounds, Components 1 and 2, described as follows.
Component 1 is an acyclic polyether derivative containing one or more than one .pi. electron rich functional units. Preferably component 1 has at least two different .pi. electron rich functional units. The .pi. electron rich units may or may not be aromatic. Examples include 1,4 dioxybenzene, 1,5 dioxynaphthalene, tetrathiafulvalene groups.
The acyclic polyether thread of Component 1 may be of the same length or of different lengths at either side of the .pi. electron rich units.
Component 1 may be of the structure provided in FIG. 1 wherein R.sup.1 and R.sup.2 are neutral terminal units at least one of which includes a cation receptor site, e.g., a crown ether unit; n is zero or a positive integer, m is independently zero or a positive integer and p is independently zero or a positive integer; X and Y each represent a covalent bond or a .pi.-electron-rich functional unit but where X may or may not be the same as Y, and at least one of X and Y is an .pi.-electron-rich functional unit. Preferably x and y are different.
The thread has terminal units which may inhibit slippage of the cyclophane from the chain. Such terminal stopper units may allow or slightly inhibit dissociation of Components 1 and 2 where they are relatively small (pseudorotaxanes) or may prevent dissociation under most normal conditions where they are larger units (rotaxanes). At least one of the terminal units is preferably a neutral cation receptor unit. Examples of suitable neutral, cation-binding terminal units are macrocyclic polyethers such as crown-ethers, azacrown ethers, thiocrown ethers cyclams, porphyrins, calixanes, calixacrowns and calixaspherands. Examples of non-cation binding terminal units are: SiR.sub.3, SiPh.sub.3, (where R may be alkyl, arylalkyl etc. Ph is phenyl etc.), OH, OR (R=alkyl), SH, NH.sub.2.
The terminal unit may be of crown form according to the formula a-crown-b where a is the number of atoms in the cyclic unit and b is the number of hetero atoms in the ring, with a varying between 8 and 45, preferably 8 and 24 and b varying between 3 and 25, preferably 3 and 10.
The crown ether may be specific for one or more types of particular cations. For instance 12-crown 4 is lithium ion specifi
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Iqbal Sayeedha
Matthews Owen Allen
Stoddart James Fraser
Tinker Nigel Dennis
British Nuclear Fuels PLC
Kim John C.
Warden Jill
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