Tetracationic cyclophanes and their use in the sequestration of polyaromatic hydrocarbons by way of complexation
AssigneeNorthwestern University
InventorsJ. Fraser Stoddart, Jonathan C. Barnes, Michal Jurícek
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Abstract
Novel tetracationic cyclophanes incorporating π-electron poor organic compounds into their ring structures, as well as methods of making the cyclophanes, are provided. The cyclophanes are able to form electron donor-acceptor complexes with a variety of polyaromatic hydrocarbons (PAHs) ranging in size, shape, and electron density. Also provided are methods of using the cyclophanes in the sequestration of PAHs in liquid or gaseous samples, the separation of PAHs from liquid or gaseous samples, the detection of PAHs in liquid samples, and the exfoliation of graphene via pseudopolyrotaxane formation.
Claims20
A cyclophane of formula I:
- wherein n≧0;
- R is independently selected from the group consisting of H, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, alkoxy groups, OH, NH2, SH, F, Cl, Br, I, P(R1)2, CHO, COOR1, COOM, CH2OR1, CH2OM, OR1, NHCOR1, CONHR1, CONHM, CON(R1)2, N3, NO2, B(OR1)2, B(OM)2, CN, N(R1)3+, P(R1)3+, PO(R1)2, and OM, where R1 is independently selected from the group consisting of H, alkyl groups, alkenyl groups, alkynyl groups, and aryl groups and M is independently selected from the group consisting of Li, Na, K, Rb and Cs;
- and X− is an organic or inorganic negatively charged ion.
A method of sequestering polyaromatic hydrocarbons from a sample comprising polyaromatic hydrocarbons, the method comprising mixing one or more cyclophanes with the sample, whereby the polyaromatic hydrocarbons form an inclusion complex with the cyclophanes;
- wherein the ring structure of the cyclophanes comprises either two 4,4′-(1,4-phenylene)bispyridinium units and two p-phenylene connected via four methylene bridges or two 4,4′-(4,4′-[n]phenylene)bispyridinium (n≧1) units and two p-phenylene units connected via four methylene bridges.
A chromatographic method of separating polyaromatic hydrocarbons in a sample comprising more than one type of polyaromatic hydrocarbon, the method comprising passing the sample over a solid support material on which one or more cyclophanes are immobilized, whereby the polyaromatic hydrocarbons undergo reversible electron donor-acceptor complexation and dissociation interactions with the polyaromatic hydrocarbons, such that different types of the polyaromatic hydrocarbons are separated from one another as they pass over the solid support material;
- wherein the ring structure of the cyclophanes comprises either two 4,4′-(1,4-phenylene)bispyridinium units and two p-phenylene connected via four methylene bridges or two 4,4′-(4,4′-[n]phenylene)bispyridinium (n≧1) units and two p-phenylene units connected via four methylene bridges.
A method for detecting the presence of polyaromatic hydrocarbons in a sample, the method comprising mixing one or more cyclophanes with the sample, whereby the polyaromatic hydrocarbons form inclusion complexes with the cyclophanes and produce a visible color change in the sample;
- and monitoring the color change;
- wherein the ring structure of the cyclophanes comprises either two 4,4′-(1,4-phenylene)bispyridinium units and two p-phenylene connected via four methylene bridges or two 4,4′-(4,4′-[n]phenylene)bispyridinium (n≧1) units and two p-phenylene units connected via four methylene bridges.
A method of exfoliating graphene nanoribbons in multi-layered graphene nanoribbon stack, the method comprising exposing the multi-layered graphene nanoribbon stack to a solution comprising one or more cyclophanes, whereby the cyclophanes form polypseudorotaxanes with the graphene nanoribbons which results in the exfoliation of individual nanoribbons as the result of Coulombic repulsion between the cyclophanes;
- wherein the ring structure of the cyclophanes comprises either two 4,4′-(1,4-phenylene)bispyridinium units and two p-phenylene connected via four methylene bridges or two 4,4′-(4,4′-[n]phenylene)bispyridinium (n≧1) units and two p-phenylene units connected via four methylene bridges.
Dependencies are inferred from the claim text.