Molecular recognition in functional materials at solid interfaces

Current Opinion in Colloid and Interface Science

Volumn 13, Issue 1-2, 2008, Pages 86-95

  Sievers, Torsten K ^a   Kurth, Dirk G ^a,b  

^a MAX PLANCK INSTITUTE OF COLLOIDS AND INTERFACES   (Germany)

^b NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

Adsorbate; Architecture; Colloids; Epitaxy; Film; Functional materials; Interface; Molecular recognition; Nanoparticle; Nanostructure; Pattern; Physisorption; SAM; Self assembled monolayer; Substrate; Surface

Indexed keywords

CRYSTAL LATTICES; CRYSTAL ORIENTATION; CRYSTALLIZATION; MONOLAYERS; PHYSISORPTION; TWO DIMENSIONAL;

COLLOIDAL SYSTEMS; FUNCTIONAL MATERIALS; PLANAR SURFACES; SOLID INTERFACES;

MOLECULAR RECOGNITION;

ADSORPTION; ATOMIC FORCE MICROSCOPY; CHEMICAL STRUCTURE; COLLOID; CRYSTALLIZATION; HYDROGEN BOND; MATERIALS; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; SCANNING TUNNELING MICROSCOPY; SOLID; SURFACE PROPERTY; TECHNOLOGY;

EID: 37249068039     PISSN: 13590294     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cocis.2007.08.007     Document Type: Review

References (63)

1. Rabe J.P., and Buchholz S. Commensurability and mobility in 2-dimensional molecular-patterns on graphite. Science 253 (1991) 424-427. The formation of two-dimensional molecular patterns of long-chain alkanes, alcohols, fatty acids and dialkylbenzenes is described. The obtained monolayers are studied by scanning tunneling microscopy (STM). In these films the molecules organize in lamellae with extended alkylchains oriented parallel to the lattice axis of the substrate.
2. Bain C.D., and Whitesides G.M. Molecular-level control over surface order in self-assembled monolayer films of thiols on gold. Science 240 (1988) 62-63. Long-chain hydroxyalkanethiols coordinate to gold surfaces through the sulfur atom produce ordered hydrophilic monolayers in which the hydroxyl groups are exposed at the outer surface. The monolayers are investigated by ellipsometry.
3. Hilson G., and Monhemius A.J. Alternatives to cyanide in the gold mining industry: what prospects for the future. J Clean Prod 14 (2006) 1158-1167
4. Binnig G., and Rohrer H. Scanning tunneling microscopy. Helv Phys. Acta 55 (1982) 726-735. A description of the fundamental principles of scanning tunneling microscopy is given.
5. Hentschke R., Schurmann B.L., and Rabe J.P. Molecular-dynamics simulations of ordered alkane chains physisorbed on graphite. J Chem Phys 96 (1992) 6213-6221
6. Foster J.S., and Frommer J.E. Imaging of liquid-crystals using a tunnelling microscope. Nature 333 (1988) 542-545
7. Manne S., and Gaub H.E. Molecular-organization of surfactants at solid-liquid interfaces. Science 270 (1995) 1480-1482. A description of the influence of the substrate on the formation of surface aggregates of the surfactant (C14TAB) and the structure of these aggregates is given.
8. Cyr D.M., Venkataraman B., and Flynn G.W. STM investigations of organic molecules physisorbed at the liquid-solid interface. Chem Mater 8 (1996) 1600-1615
9. Stabel A., Heinz R., Rabe J.P., Wegner G., Deschryver F.C., Corens D., et al. STM investigation of 2D crystals of anthrone derivatives on graphite - analysis of molecular-structure and dynamics. J Phys Chem 99 (1995) 8690-8697. The influence of the functional modification of alkylated anthrone derivatives on the structure of their two-dimensional crystals is studied by scanning tunneling microscopy.
10. De Feyter S., and De Schryver F.C. Two-dimensional supramolecular self-assembly probed by scanning tunneling microscopy. Chem Soc Rev 32 (2003) 139-150
11. Jäckel F., Ai M., Wu J.S., Mullen K., and Rabe J.P. Solvent molecules in an epitaxially grown scaffold of star-shaped nanographenes. J Am Chem Soc 127 (2005) 14580-14581. The architecture of star-shaped nanographenes on graphite is described. A detailed analysis of the coaggregation of the graphenes and solvents is investigated by scanning tunneling microscopy (STM). The images of these films show a triangular or star-like structure, depending on the tunneling current applied while investigating with STM.
12. De Feyter S., Gesquiere A., Abdel-Mottaleb M.M., Grim P.C.M., De Schryver F.C., Meiners C., et al. Scanning tunneling microscopy: a unique tool in the study of chirality, dynamics, and reactivity in physisorbed organic monolayers. Acc Chem Res 33 (2000) 520-531
13. De Feyter S., and De Schryver F.C. Self-assembly at the liquid/solid interface: STM reveals. Phys Chem B 109 (2005) 4290-4302. An extensive description of the influence of weak interactions on the formation of patterned surfaces is given. The surfaces are analyzed by STM.
14. Mourran A., Ziener U., Moller M., Suarez M., and Lehn J.M. Homo- and heteroassemblies of lactim/lactam recognition patterns on highly ordered pyrolytic graphite: an STM investigation. Langmuir 22 (2006) 7579-7586
15. Nakanishi T., Schmitt W., Michinobu T., Kurth D.G., and Ariga K. Hierarchical supramolecular fullerene architectures with controlled dimensionality. Chem Comm (2005) 5982-5984
16. Nakanishi T., Miyashita N., Michinobu T., Wakayama Y., Tsuruoka T., Ariga K., et al. Perfectly straight nanowires of fullerenes bearing long alkyl chains on graphite. J Am Chem Soc 128 (2006) 6328-6329. The formation of perfectly straight nanowires of alkyl substituted functionalized fullerenes is described. These structures are investigated by atomic force microscopy and scanning tunneling microscopy, and can be understood by the formation of head-to-head arranged dimers of the fullerenes on the surface.
17. De Feyter S., Abdel-Mottaleb M.M.S., Schuurmans N., Verkuijl B.J.V., van Esch J.H., Feringa B.L., et al. Metal ion complexation: a route to 2D templates?. Chem Eur J 10 (2004) 1124-1132
18. Lei S.B., Wang C., Yin S.X., Wang H.N., Xi F., Liu H.W., et al. Surface stabilized porphyrin and phthalocyanine two-dimensional network connected by hydrogen bonds. J Phys Chem B 105 (2001) 10838-10841
19. Yoshimoto S., Sawaguchi T., Su W., Jiang J.Z., and Kobayashi N. Superstructure formation and rearrangement in the adlayer of a rare-earth-metal triple-decker sandwich complex at the electrochemical interface. Angew Chem Int Ed 46 (2007) 1071-1074
20. Suto K., Yoshimoto S., and Itaya K. Electrochemical control of the structure of two-dimensional supramolecular organization consisting of phthalocyanine and porphyrin on a gold single-crystal surface. Langmuir 22 (2006) 10766-10776
21. Griessl S., Lackinger M., Edelwirth M., Hietschold M., and Heckl W.M. Self-assembled two-dimensional molecular host-guest architectures from trimesic acid. Single Mol 3 (2002) 25-31. The adsorption of trimesic acid to a graphite surface was studied. The resulting films exhibit an architecture, which is based on octameric and trimeric clusters of trimesic acid and can be used as a template for host-guest systems.
22. Green J.E., Choi J.W., Boukai A., Bunimovich Y., Johnston-Halperin E., DeIonno E., et al. A 160-kilobit molecular electronic memory patterned at 10(11) bits per square centimetre. Nature 445 (2007) 414-417. The authors give a detailed presentation on the assembly of a random access memory (RAM) device, which was build-up by the self-assembly of bistable [2]rotaxanes on 400 silicon and titanium nanowires. The advantage of this approach is the robustness of the obtained device, resulting from the defect tolerance of self-assembled systems.
23. Severin N., Rabe J.P., and Kurth D.G. Fully extended polyelectrolyte-amphiphile complexes adsorbed on graphite. J Am Chem Soc 126 (2004) 3696-3697
24. Severin N., Sokolov I.M., Miyashita N., Kurth D.G., and Rabe J.P. Self-sorting of polyelectrolyte-amphiphile complexes on a graphite surface. Macromolecules 40 (2007) 5182-5186
25. Kurth D.G., Severin N., and Rabe J.P. Perfectly straight nanostructures of metallosupramolecular coordination-polyelectrolyte amphiphile complexes on graphite. Angew Chem Int Ed 41 (2002) 3681-3683. The formation of perfectly straight nanorods is described. These rods were obtained by a multi-step self-assembly of transition metal ions, ligands, and amphiphiles on an alkane patterned surface.
26. Severin N., Okhapkin I.M., Khokhlov A.R., and Rabe J.P. Adsorption of polyelectrolyte molecules to a nanostructured monolayer of amphiphiles. Nano Lett 6 (2006) 1018-1022
27. Kiebele A., Bonifazi D., Cheng F.Y., Stohr M., Diederich F., Jung T., et al. Adsorption and dynamics of long-range interacting fullerenes in a flexible, two-dimensional, nanoporous porphyrin network. Chemphyschem 7 (2006) 1462-1470
28. Bonifazi D., Spillmann H., Kiebele A., de Wild M., Seiler P., Cheng F.Y., et al. Supramolecular patterned surfaces driven by cooperative assembly of C-60 and porphyrins on metal substrates. Angew Chem Int Ed 43 (2004) 4759-4763. The formation of an addressable supramolecular surface architecture obtained by self-assembly of fullerenes and porphyrins on surfaces is given. The arrangement of the fullerenes on the patterned layer is controlled by the prophyrin structure. The structure of these architectures is investigated by scanning tunneling microscopy.
29. Miyashita N, Möhwald H, Kurth D.G., accepted for publication. 2-D Structure of Unsaturated Fatty Acid Amide Mono- and Multilayer on Graphite: Self-Assembly and Thermal Behavior. Chem Mater.
30. Nuzzo R.G., and Allara D.L. Adsorption of bifunctional organic disulfides on gold surfaces. J Am Chem Soc 105 (1983) 4481-4483. A description of self-assembled monolayers is given. These films were formed by organic disulfides on gold and characterized by reflectance infrared spectroscopy.
31. Troughton E.B., Bain C.D., Whitesides G.M., Nuzzo R.G., Allara D.L., and Porter M.D. Monolayer films prepared by the spontaneous self-assembly of symmetrical and unsymmetrical dialkyl sulfides from solution onto gold substrates - structure, properties, and reactivity of constituent functional-Groups. Langmuir 4 (1988) 365-385. The formation of self-assembled monolayers of alkyl disulfides on gold is described. The thin films are extensively investigated by different techniques, such as ellipsometry.
32. Bain C.D., Troughton E.B., Tao Y.T., Evall J., Whitesides G.M., and Nuzzo R.G. Formation of monolayer films by the spontaneous assembly of organic thiols from solution onto gold. J Am Chem Soc 111 (1989) 321-335. Long-chain alkanethiols adsorb form solution onto gold surfaces and form ordered oriented monolayers. In this study contact angle microscopy and ellipsometry were used to study the kinetics of adsorption of monolayer films and explore the conditions necessary to obtain high-quality films.
33. Laibinis P.E., and Whitesides G.M. Self-assembled monolayers of N-alkanethiolates on copper are barrier films that protect the metal against oxidation by air. J Am Chem Soc 114 (1992) 9022-9028. Self-assembled monolayers on copper surfaces slow the oxidation of the surface by inhibiting the reaction with atmospheric oxygen. A detailed analysis of the preparation and the properties of these monolayers is given.
34. Laibinis P.E., Hickman J.J., Wrighton M.S., and Whitesides G.M. Orthogonal self-assembled monolayers - alkanethiols on gold and alkane carboxylic-acids on alumina. Science 245 (1989) 845-847. The formation of two self-assembled monolayers, independently but simultaneously, by adsorption of two different adsorbates on a substrate exposing two different materials at its surface is described.
35. Kumar A., and Whitesides G.M. Features of gold having micrometer to centimeter dimensions can be formed through a combination of stamping with an elastomeric stamp and an alkanethiol ink followed by chemical etching. Appl Phys Lett 63 (1993) 2002-2004. A description on how micro contact printing could be used to produce well-defined features of gold. This technique involves the patterning of self-assembled monolayers on a gold substrate using an elastomer stamp.
36. Tour J.M., Jones L., Pearson D.L., Lamba J.J.S., Burgin T.P., Whitesides G.M., et al. Self-assembled monolayers and multilayers of conjugated thiols, alpha, omega-dithiols, and thioacetyl-containing adsorbates-understanding attachments between potential molecular wires and gold surfaces. J Am Chem Soc 117 (1995) 9529-9534. Studies of self-assembled monolayers (SAMs) and multilayers on gold surfaces of rigid-rod conjugated oligomers that have different sulfur-containing end-groups are described. The SAMs were analyzed using ellipsometry, x-ray photoelectron spectroscopy and infrared external reflectance spectroscopy.
37. Kagan C.R., Afzali A., Martel R., Gignac L.M., Solomon P.M., Schrott A.G., et al. Evaluations and considerations for self-assembled monolayer field-effect transistors. Nano Lett 3 (2003) 119-124
38. Frisbie C.D., Rozsnyai L.F., Noy A., Wrighton M.S., and Lieber C.M. Functional-group imaging by chemical force microscopy. Science 265 (1994) 2071-2074. A force microscope has been used to measure the adhesive and friction forces between molecularly modified tips and organic monolayers terminating in a lithography defined pattern of distinct functional groups.
39. Akari S., Horn D., Keller H., and Schrepp W. Chemical imaging by scanning force microscopy. Adv Mater 7 (1995) 549-551
40. Lee T.R., Carey R.I., Biebuyck H.A., and Whitesides G.M. The wetting of monolayer films exposing ionizable acids and bases. Langmuir 10 (1994) 741-749
41. Beulen M.W.J., Bugler J., Lammerink B., Geurts F.A.J., Biemond E.M.E.F., van Leerdam K.G.C., et al. Self-assembled monolayers of heptapodant beta-cyclodextrins on gold. Langmuir 14 (1998) 6424-6429
42. Auletta T., Dordi B., Mulder A., Sartori A., Onclin S., Bruinink C.M., et al. Writing patterns of molecules on molecular printboards. Angew Chem Int Ed 43 (2004) 369-373
43. Nijhuis C.A., Yu F., Knoll W., Huskens J., and Reinhoudt D.N. Multivalent dendrimers at molecular printboards: influence of dendrimer structure on binding strength and stoichiometry and their electrochemically induced desorption. Langmuir 21 (2005) 7866-7876. Three different types of ferrocenyl functionalized dendrimers with various spacers groups were adsorbed at self-assembled monolayers (SAMs) bearing multiple cyclodextrin units. The dendrimers formed kinetically stable supramolecular assemblies on these SAMs based on multivalent interactions.
44. Nijhuis C.A., Huskens J., and Reinhoudt D.N. Binding control and stoichiometry of ferrocenyl dendrimers at a molecular printboard. J Am Chem Soc 126 (2004) 12266-12267
45. Zhang S., Palkar A., and Echegoyen L. Selective anion sensing based on tetra-amide calix[6]arene derivatives in solution and immobilized on gold surfaces via self-assembled monolayers. Langmuir 22 (2006) 10732-10738
46. Rief M., Gautel M., Oesterhelt F., Fernandez J.M., and Gaub H.E. Reversible unfolding of individual titin immunoglobulin domains by AFM. Science 276 (1997) 1109-1112. Single-molecule atomic force microscopy was used to investigate the mechanical properties of titin. Individual titin molecules were repeatedly stretched, and the applied forces were recorded to determine the energy needed for unfolding of titin and the one released upon restoring the structure of the titin.
47. Florin E.L., Moy V.T., and Gaub H.E. Adhesion forces between individual ligand-receptor pairs. Science 264 (1994) 415-417. The adhesion force between the tip of an atomic force microscope cantilever functionalized with avidin and agarose beads functionalized with biotin was measured.
48. Eckel R., Ros R., Decker B., Mattay J., and Anselmetti D. Supramolecular chemistry at the single-molecule level. Angew Chem Int Ed 44 (2005) 484-488
49. Schafer C., Decker B., Letzel M., Novara F., Eckel R., Ros R., et al. On the way to supramolecular photochemistry at the single-molecule level. Pure Appl Chem 78 (2006) 2247-2259
50. Schafer C., Eckel R., Ros R., Mattay J., and Anselmetti D. Photochemical single-molecule affinity switch. J Am Chem Soc 129 (2007) 1488-1489
51. Maskus M., and Abruna H.D. Synthesis and characterization of redox-active metal complexes sequentially self-assembled onto gold electrodes via a new thiol-terpyridine ligand. Langmuir 12 (1996) 4455-4462. The synthesis of a thiol-modified terpyridine ligand is reported, as well as the formation of complexes on a gold surface. This formation leads to a surface growth of coordination polymers, which was observed by cyclic voltammetry.
52. Wanunu M., Vaskevich A., Shanzer A., and Rubinstein I. Divergent growth of coordination dendrimers on surfaces. J Am Chem Soc 128 (2006) 8341-8349
53. Wanunu M., Vaskevich A., Cohen S.R., Cohen H., Arad-Yellin R., Shanzer A., et al. Branched coordination multilayers on gold. J Am Chem Soc 127 (2005) 17877-17887
54. Wanunu M., Popovitz-Biro R., Cohen H., Vaskevich A., and Rubinstein I. Coordination-based gold nanoparticle layers. J Am Chem Soc 127 (2005) 9207-9215. Gold nanoparticle mono- and multilayers were constructed on gold surfaces using coordination chemistry. The films were investigated by UV-vis spectroscopy, transmission electron microscopy, ellipsometry, and atomic force microscopy.
55. Coll C., Martinez-Manez R., Marcos M.D., Sancenon F., and Soto J. A simple approach for the selective and sensitive colorimetric detection of anionic surfactants in water. Angew Chem Int Ed 46 (2007) 1675-1678
56. Fritz J., Baller M.K., Lang H.P., Rothuizen H., Vettiger P., Meyer E., et al. Translating biomolecular recognition into nanomechanics. Science 288 (2000) 316-318. Biomolecular recognition on surfaces leads to stress within the film covering the surface. This stress could be translated into a bending of the substrate, if the substrates are as thin as atomic force microscopy cantilevers. The authors show how this bending was used to investigate molecular recognition at surfaces.
57. Baller M.K., Lang H.P., Fritz J., Gerber C., Gimzewski J.K., Drechsler U., et al. A cantilever array-based artificial nose. Ultramicroscopy 82 (2000) 1-9
58. Battiston F.M., Ramseyer J.P., Lang H.P., Baller M.K., Gerber C., Gimzewski J.K., et al. A chemical sensor based on a microfabricated cantilever array with simultaneous resonance-frequency and bending readout. Sens Actuators, B 77 (2001) 122-131
59. Shenhar R., and Rotello V.M. Nanoparticles: scaffolds and building blocks. Acc Chem Res 36 (2003) 549-561. It is described how nanoparticles could act as devices with tunable specificity and environmental response, and how this approach could be used to explore the use of nanoparticles as building blocks for the creation of nanocomposite materials.
60. Guerrini L., Garcia-Ramos J.V., Domingo C., and Sanchez-Cortes S. Functionalization of Ag nanoparticles with dithiocarbamate calix[4]arene as an effective supramolecular host for the surface-enhanced Raman scattering detection of polycyclic aromatic hydrocarbons. Langmuir 22 (2006) 10924-10926
61. Leung K.C.F., Nguyen T.D., Stoddart J.F., and Zink J.I. Supramolecular nanovalves controlled by proton abstraction and competitive binding. Chem Mater 18 (2006) 5919-5928
62. Nguyen T.D., Liu Y., Saha S., Leung K.C.F., Stoddart J.F., and Zink J.I. Design and optimization of molecular nanovalves based on redox-switchable bistable rotaxanes. J Am Chem Soc 129 (2007) 626-634. The preparation of redox-controllable molecular nanovalves based on mesoporous silica nanoparticles is described. These nanovalves can be classified as having IN and OUT locations, based on the position of tethered bistable [2]rotaxanes. Depending on the position an analysis of the loading and unloading of the particles is given.
63. Maxwell D.J., Taylor J.R., and Nie S.M. Self-assembled nanoparticle probes for recognition and detection of biomolecules. J Am Chem Soc 124 (2002) 9606-9612. Colloidal gold nanoparticles are used for molecular recognition of DNA. The recognition event is marked by the appearance of fluorescence, which was quenched before DNA was adsorbed to the particle.