Self-assembly of well-defined structures by hydrogen bonding

Current Opinion in Colloid and Interface Science

Volumn 4, Issue 1, 1999, Pages 24-32

  Sijbesma, Rint P ^a   Meijer, Ew ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

POLYMER;

HYDROGEN BOND; POLYMERIZATION; REVIEW; SYNTHESIS;

EID: 0033066433     PISSN: 13590294     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1359-0294(99)00011-4     Document Type: Article

References (52)

1. Lawrence DS, Jiang T, Levett M: Self-assembling supramolecular complexes. Chem Rev 1995, 95:2229-2260.
2. Brienne MJ, Gabard J, Leclerq M, Lehn J-M, Cheve M: Synthesis of chiral bicyclic bis-lactam components for the controlled self-assembly of hydrogen-bonded arrays. Helv Chim Acta 1997, 80:856-875.
3. Wang Y, Decken A, Deslongchamps G: Synthesis and supramolecular self-assembly of a bicyclic dilactam. Tetrahedron 1998, 54:9043-9054.
4. Suarez E, Lehn J-M, Zimmerman SC, Skoulios A, Heinrich B: Supramolecular liquid crystals. Self-assembly of a trimeric supramolecular disk and its self-organization into a columnar discotic mesophase. J Am Chem Soc 1998, 120:9526-9532.
5. Kolutchin SV, Zimmerman SC: Self-assembly mediated by the donor-donor-acceptors: Acceptor-acceptor-donor (DDA:AAD) hydrogen-bonding motif: formation of a robust hexameric aggregate. J Am Chem Soc 1998, 120:9092-9093. The high information content and stability of triple hydrogen bonds is demonstrated in an elegant system.
6. Tirumala S, Davis J: Self-assembled ionophores. An isoguanosine-K+ octamer. J Am Chem Soc 1997, 119:2769-2776.
7. Seela F, Wei C: 7-Deazaisoguanine quartets: self-assembled oligonucleotides lacking the Hoogsteen motif. Chem Commun 1997:1869-1870.
8. Mammen M, Shakhnovich EI, Deutch JM, Whitesides GM: Estimating the entropic cost of self-assembly of multiparticle hydrogen-bonded aggregates based on the cyanuric acid-melamine lattice. J Org Chem 1998, 63:3821-3830.
9. 1H NMR spectroscopy of the imide region can distinguish isomers of hydrogen-bonded aggregates. J Org Chem 1997, 62:1891-1895.
10. 1H nuclear magnetic resonance spectroscopy when CA is an optically-active isocyanuric acid. J Org Chem 1997, 62:2619-2621.
11. Simanek EE, Isaacs L, Li X, Wang CCC, Whitesides GM: Self assembly of zinc porphyrins around the periphery of hydrogen-bonded aggregates that bear imidazole groups. J Org Chem 1997, 62:8994-9000. One of the early examples of the use of 'orthogonal' non-covalent interactions to obtain a multichromophoric array.
12. Huck WTS, Hulst R, Timmerman P, van Veggel FCJM, Reinhoudt DN: Non-covalent synthesis of nanostructures - combining coordination chemistry and hydrogen-bonding. Angew Chem Int Ed Engl 1997, 36:1006-1008. Just as in the previous reference, two different types of non-covalent interactions are used to obtain a large complex.
13. Timmerman P, Vreekamp RH, Hulst R, Verboom W, Reinhoudt DN, Rissanen K, Udachin KA, Ripmeester J: Non-covalent assembly of functional groups on calix (4)arene molecular boxes. Chem Eur J 1997, 3:1823-1832.
14. + labeling. Angew Chem Int Ed Engl 1998, 37:1247-1251.
15. Crego Calama M, Hulst R, Fokkens R, Nibbering NMM, Timmerman P, Reinhoudt DN: Libraries of non-covalent hydrogen-bonded assemblies - combinatorial synthesis of supramolecular systems. Chem Commun 1998:1021-1022.
16. Conn MM, Rebek J Jr: Self-assembling capsules. Chem Rev 1997, 97:1647-1668.
17. Fujita M Aguro D, Miyazawa M, Oka H, Yamaguchi K, Ogura D: Self-assembly of ten molecules into nanometre-sized organic host frameworks. Nature 1995, 378:469-471.
18. Cram DJ, Cram JM: Container Molecules and their Guests. Cambridge: Royal Society of Chemistry; 1994.
19. Timmerman P, Verboom W, van Veggel FCJM, van Hoorn WP, Reinhoudt DN: An organic molecule with a rigid cavity of nanosize dimensions. Angew Chem Int Ed Engl 1994, 33:1292-1294.
20. Jansen JFGA, de Brabander-van den Berg EMM, Meijer EW: Encapsulation of guest molecules into a dendritic box. Science 1994, 266:1226-1228.
21. Baars MWPL, Froehling PE, Meijer EW: Liquid-liquid extractions using poly(propylene imine) dendrimers with an apolar periphery. Chem Commun 1997:1959-1960.
22. Sijbesma RP, Nolte RJM: Molecular clips and cages derived from glycoluril. Top Curr Chem 1995, 175:25-56.
23. Wyler M, de Mendoza J, Rebek J Jr: A synthetic cavity assemblies through self complementary hydrogen bonds. Angew Chem Int Ed Engl 1993, 32:1699.
24. Szabo T, Hilmersson G, Rebek J Jr: Dynamics of assembly and guest exchange in the tennis ball. J Am Chem Soc 1998, 120:6193-6194.
25. Meissner R, Garcias X, Mecozzi S, Rebek J Jr: Synthesis and assembly of new molecular hosts - solvation and the energetics of encapsulation. J Am Chem Soc 1997, 119:77-85.
26. Mecozzi S, Rebek J Jr: The 55% solution: a formula for molecular recognition in the liquid state. Chem Eur J 1998, 4:1016-1022. Optimal binding of guests in a cavity is shown to occur when approximately 55% of the space is occupied, a number which is comparable to the packing factor of molecules in liquids.
27. Oleary BM, Grotzfeld RM, Rebek J Jr: Ring inversion dynamics of encapsulated cyclohexane. J Am Chem Soc 1997, 119:11701-11702.
28. Tokunaga Y, Rudkevich DM, Rebek J Jr: Solvation and the synthesis of self-assembled capsules. Angew Chem Int Ed Engl 1997, 36:2656-2659.
29. Rivera JM, Martin T, Rebek J Jr: Chiral spaces - Dissymmetric capsules through self-assembly. Science 1998, 279:1021-1023.
30. Tokunaga Y, Rebek J Jr: Chiral capsules - Surfaces bind camphor derivatives. J Am Chem Soc 1998, 120:66-69.
31. Kang JM, Hilmersson G, Santamaria J, Rebek J Jr: Diels-Alder reactions through reversible encapsulation. J Am Chem Soc 1998, 120:3650-3656.
32. Kang JM, Santamaria J, Hilmersson G, Rebek J Jr: Self-assembled molecular capsule catalyzes a Diels-Alder reaction. J Am Chem Soc 1998, 120:7389-7390. Rate acceleration and turnover of a Diels-Alder reaction make this a very interesting example of a functional capsule.
33. Mogck O, Paulus EF, Boehmer V, Thondorf I, Vogt W: Hydrogen-bonded dimers of tetraurea calix(4) by single crystal X-ray analysis. Chem Commun 1996:2533-2534.
34. Castellano RK, Kim BH, Rebek J Jr: Chiral capsules - Asymmetric binding in calixarene-based dimers. J Am Chem Soc 1997, 119:12671-12672.
35. Verboom W, Smeets WJJ, Spek AL, Reinhoudt DN, Struck O: Calix(4)arene dimers; self-assembly via hydrogen bonding at the upper rim. J Chem Soc Perkin Trans 2 1997:223-227.
36. Arduini A, Domiano L, Ogliosi L, Pochini A, Secchi A, Ungaro R: Self-assembled hydrogen-bonded molecular cages of calix(6) derivatives. J Org Chem 1997, 62:7866-7868.
37. Martín T, Obst U, Rebek J Jr: Molecular assembly and encapsulation directed by hydrogen-bonding preferences and the filling of space. Science 1998, 281:1842-1845.
38. MacGillivray LR, Atwood JL: A chiral spherical molecular assembly held together by 60 hydrogen bonds. Nature 1997, 389:469-472.
39. Heinz T, Rudkevich DM, Rebek J Jr: Pairwise selection of guests in a cylindrical molecular capsule of nanometre dimensions. Nature 1998, 394:764-766. In order to occupy the optimum fraction of space in the cavity, the capsule described in this paper selectively binds one larger and one smaller molecule.
40. Lehn JM: Supramolecular chemistry - molecular information and the design of supramolecular materials. Makromol Chem Makromol Symp 1993, 69:1-17.
41. Kotera M, Lehn JM, Vigneron JP: Self-assembled supramolecular rigid rods. J Chem Soc Chem Commun 1994:197-199.
42. Gulik-Krzywicki T, Fouquey C, Lehn JM: Electron-microscopic study of supramolecular liquid-crystalline polymers formed by molecular-recognition-directed self-assembly from complementary chiral components. Proc Natl Acad Sci USA 1993, 90:163-167.
43. Kato T: Hydrogen bonding and the self-assembly of supramolecular liquid crystalline materials. Macromol Symp 1995, 98:311-326.
44. Zimerman N, Moore J, Zimmerman SC: Polymer chemistry comes full circle. Chem Ind 1998:604-610.
45. Lee CM, Griffin AC: Hydrogen bonding as the origin of both liquid crystallinity and polymer formation in some supramolecular materials. Macromol Symp 1997, 117:281-290. The interplay between liquid crystallinity and aggregation is investigated in this paper. Fiber formation and a glass transition are observed for molecules which aggregate via pyridine-carboxylic acid hydrogen bonds.
46. Palmans ARA, Vekemans JAJM, Fischer H, Hikmet RA, Meijer EW: Extended core discotic liquid crystals based on the intramolecular H-bonding in N-acylated 2,2′-bipyridine-3,3′-diamine moieties. Chem Eur J 1997, 3:300-307.
47. Palmans ARA, Vekemans JAJM, Havinga EE, Meijer EW: Sergeants and soldiers principle in chiral columnar stacks of disc shaped molecules with C3 symmetry. Angew Chem Int Ed Engl 1997, 36:2648-2651.
48. Beijer FH, Sijbesma RP, Kooijman H, Spek AL, Meijer EW: Strong dimerization of ureidopyrimidones via quadruple hydrogen bonding in a donor-donor-acceptor-acceptor array. J Am Chem Soc 1998, 120:6761-6769.
49. Sijbesma RP, Beijer FH, Brunsveld L, Folmer BJB, Hirschberg JHKK, Lange RFM, Lowe JKL, Meijer EW: Reversible polymers formed from self-complementary monomers using quadruple hydrogen-bonding. Science 1997, 278:1601-1604. In this article polymers which are held together by hydrogen bonds are shown to have a high degree of polymerization and polymer-like properties, such as viscoelasticity.
50. Folmer BJB, Cavini, E, Sijbesma, RP, Meijer, EW: Photo-induced depolymerization of reversible supramolecular polymers. Chem Commun 1998:1847-1848.
51. Castellano RK, Rudkevich DM, Rebek J Jr: Polycaps - Reversibly formed polymeric capsules. Proc Natl Acad Sci USA 1997, 94:7132-7137.
52. Castellano RK, Rebek J Jr: Formation of discrete, functional assemblies and informational polymers through the hydrogen-bonding preferences of calixarene aryl and sulfonyl tetraureas. J Am Chem Soc 1998, 120:3657-3663.