Supramolecular chemistry
Supramolecular chemistry refers to the branch of chemistry concerning chemical systems composed of a discrete number of molecules. The strength of the forces responsible for spatial organization of the system range from weak intermolecular forces, electrostatic charge, or hydrogen bonding to strong covalent bonding, provided that the electronic coupling strength remains small relative to the energy parameters of the component.[1][2] While traditional chemistry concentrates on the covalent bond, supramolecular chemistry examines the weaker and reversible non-covalent interactions between molecules.[3] These forces include hydrogen bonding, metal coordination, hydrophobic forces, van der Waals forces, pi–pi interactions and electrostatic effects.[4][5]
Important concepts advanced by supramolecular chemistry include molecular self-assembly, molecular folding, molecular recognition, host–guest chemistry, mechanically-interlocked molecular architectures, and dynamic covalent chemistry.[6] The study of non-covalent interactions is crucial to understanding many biological processes that rely on these forces for structure and function. Biological systems are often the inspiration for supramolecular research.
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Self-assembly of a circular double helicate[7]
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Host–guest complex within another host (cucurbituril)[8]
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An example of a host–guest chemistry[10]
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Host–guest complex with a p-xylylenediammonium bound within a cucurbituril[11]
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Two pyrene butyric acids bound within a C-hexylpyrogallol[4]arenes nanocapsule. The side chains of the pyrene butyric acids are omitted.[13]
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Atructure of two isophthalic acids bound to a host molecule through hydrogen bonds[14]
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Structure of a short peptide L-Lys-D-Ala-D-Ala (bacterial cell wall precursor) bound to the antibiotic vancomycin[15]
- ^ Lehn, J. (1993). "Supramolecular Chemistry". Science. 260 (5115): 1762–23. Bibcode:1993Sci...260.1762L. doi:10.1126/science.8511582. PMID 8511582.
- ^ Lehn, J. (1995). Supramolecular Chemistry. Wiley-VCH. ISBN 978-3-527-29311-7.
- ^ Schneider, H. (2009). "Binding Mechanisms in Supramolecular Complexes". Angew. Chem. Int. Ed. Engl. 48 (22): 3924–77. doi:10.1002/anie.200802947. PMID 19415701.
- ^ Biedermann, F.; Schneider, H.J. (2016). "Experimental Binding Energies in Supramolecular Complexes". Chem. Rev. 116 (9): 5216–5300. doi:10.1021/acs.chemrev.5b00583. PMID 27136957.
- ^ Steed, Jonathan W.; Atwood, Jerry L. (2009). Supramolecular Chemistry (2nd ed.). Wiley. doi:10.1002/9780470740880. ISBN 978-0-470-51234-0.
- ^ Oshovsky, G. V.; Reinhoudt, D. N.; Verboom, W. (2007). "Supramolecular Chemistry in Water" (PDF). Angewandte Chemie International Edition. 46 (14): 2366–93. doi:10.1002/anie.200602815. PMID 17370285.
- ^ Hasenknopf, B.; Lehn, J. M.; Kneisel, B. O.; Baum, G.; Fenske, D. (1996). "Self-Assembly of a Circular Double Helicate". Angewandte Chemie International Edition in English. 35 (16): 1838–1840. doi:10.1002/anie.199618381.
- ^ Day, A. I.; Blanch, R. J.; Arnold, A. P.; Lorenzo, S.; Lewis, G. R.; Dance, I. (2002). "A Cucurbituril-Based Gyroscane: A New Supramolecular Form". Angewandte Chemie International Edition. 41 (2): 275–7. doi:10.1002/1521-3773(20020118)41:2<275::AID-ANIE275>3.0.CO;2-M. PMID 12491407.
- ^ Bravo, J. A.; Raymo, F. I. M.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. (1998). "High Yielding Template-Directed Syntheses of [2]Rotaxanes". European Journal of Organic Chemistry. 1998 (11): 2565–2571. doi:10.1002/(SICI)1099-0690(199811)1998:11<2565::AID-EJOC2565>3.0.CO;2-8.
- ^ Anderson, S.; Anderson, H. L.; Bashall, A.; McPartlin, M.; Sanders, J. K. M. (1995). "Assembly and Crystal Structure of a Photoactive Array of Five Porphyrins". Angewandte Chemie International Edition in English. 34 (10): 1096–1099. doi:10.1002/anie.199510961.
- ^ Freeman, W. A. (1984). "Structures of the p-xylylenediammonium chloride and calcium hydrogensulfate adducts of the cavitand 'cucurbituril', C36H36N24O12". Acta Crystallographica Section B. 40 (4): 382–387. Bibcode:1984AcCrB..40..382F. doi:10.1107/S0108768184002354.
- ^ Schmitt, J. L.; Stadler, A. M.; Kyritsakas, N.; Lehn, J. M. (2003). "Helicity-Encoded Molecular Strands: Efficient Access by the Hydrazone Route and Structural Features". Helvetica Chimica Acta. 86 (5): 1598–1624. doi:10.1002/hlca.200390137.
- ^ Dalgarno, S. J.; Tucker, S. A.; Bassil, D. B.; Atwood, J. L. (2005). "Fluorescent Guest Molecules Report Ordered Inner Phase of Host Capsules in Solution". Science. 309 (5743): 2037–9. Bibcode:2005Sci...309.2037D. doi:10.1126/science.1116579. PMID 16179474. S2CID 41468421.
- ^ Bielawski C, Chen Y, Zhang P, Prest P, Moore JS (1998). "A modular approach to constructing multi-site receptors for isophthalic acid". Chemical Communications (12): 1313–4. doi:10.1039/a707262g.
- ^ Knox JR, Pratt RF (July 1990). "Different modes of vancomycin and D-alanyl-D-alanine peptidase binding to cell wall peptide and a possible role for the vancomycin resistance protein" (Free full text). Antimicrobial Agents and Chemotherapy. 34 (7): 1342–1347. doi:10.1128/AAC.34.7.1342. PMC 175978. PMID 2386365.