Self-assembled π-conjugated macromolecular architectures - A soft solution process based on Schiff base coupling

Current Opinion in Colloid and Interface Science

Volumn 19, Issue 2, 2014, Pages 140-154

  Kunitake, Masashi ^a   Higuchi, Rintaro ^a   Tanoue, Ryota ^a   Uemura, Shinobu ^b  

^a KUMAMOTO UNIVERSITY   (Japan)

^b KAGAWA UNIVERSITY   (Japan)

Author keywords

"Bottom up" nanotechnology; Chemical liquid deposition; Covalent supramolecular nanoarchitectures; Dynamic reversible reaction; Poly(azomethine); Schiff base coupling reaction; Soft solution process; Surface mediated polycondensation; Thermodynamic self assembly

Indexed keywords

CHEMICAL BONDS; DEPOSITION; FUNCTIONAL GROUPS; FUNCTIONAL MATERIALS; LIQUIDS; MACROMOLECULES; POLYCONDENSATION; POLYMERS; SELF ASSEMBLY;

AZOMETHINE; CHEMICAL LIQUID DEPOSITION; NANOARCHITECTURES; REVERSIBLE REACTION; SCHIFF BASE COUPLING REACTION; SOFT SOLUTION;

SUPRAMOLECULAR CHEMISTRY;

ADLAYER; NANOMATERIAL; NANOMESH; NANORIBBON; POLYMER; PORPHYRIN; SCHIFF BASE;

ADSORPTION; AQUEOUS SOLUTION; CHEMICAL STRUCTURE; NANOTECHNOLOGY; POLYMERIZATION; REVIEW; SCANNING TUNNELING MICROSCOPY;

EID: 84901985560     PISSN: 13590294     EISSN: 18790399     Source Type: Journal    
DOI: 10.1016/j.cocis.2014.03.003     Document Type: Review

References (68)

1. Lehn J.-M. Toward self-organization and complex matter. Science 2002, 295:2400-2403.
2. Samorì P., Cacialli F. Functional Supramolecular Architectures 2011, Wiley-VCH, Weinheim.
3. Tsukruk V.V. Assembly of supramolecular polymers in ultrathin films. Prog Polym Sci 1997, 22:247-311.
4. Endo H., Kado Y., Mitusishi M., Miyashita T. Fabrication of free-standing hybrid nanosheets organized with polymer Langmuir-Blodgett films and gold nanoparticles. Macromolecules 2006, 39:5559-5563.
5. Decher G. Fuzzy nanoassemblies: toward layered polymeric multicomposites. Science 1997, 277:1232-1237.
6. Higuchi R., Hirano M., Ashaduzzaman M., Yilmaz N., Sumino T., Kodama D., et al. Construction and characterization of molecular nonwoven fabrics consisting of cross-linked poly(γ-methyl-L-glutamate). Langmuir 2013, 29:7478-7487.
7. Yamada N., Komatsu T., Yoshinaga H., Edo S., Kunitake M. Self-supporting elastic film without covalent linkages due to hierarchic integration of β-sheet assemblage. Angew Chem Int Ed 2003, 42:5496-5499.
8. Ariga K., Hill J.P., Ji Q. Layer-by-layer assembly as a versatile bottom-up nanofabrication technique for exploratory research and realistic application. Phys Chem Chem Phys 2007, 9:2319-2340.
9. Kitagawa S., Kitaura R., Noro S.I. Functional porous coordination polymers. Angew Chem Int Ed 2004, 43:2334-2375.
10. CÔté A.P., Benin A.I., Ockwig N.W., Matzger A.J., O'Keeffe M., Yaghi O.M. Porous, crystalline, covalent organic frameworks. Science 2005, 310:1166-1170.
11. Thomas A. Functional materials: from hard to soft porous frameworks. Angew Chem Int Ed 2010, 49:8328-8344.
12. Foo M.L., Matsuda R., Kitagawa S. Functional hybrid porous coordination polymers. Chem Mater 2014, 26:310-322.
13. Makiura R., Motoyama S., Umemura Y., Yamanaka H., Sakata O., Kitagawa H. Surface nano-architecture of a metal-organic framework. Nat Mater 2010, 9:565-571.
14. Bétard A., Fischer R.A. Metal-organic framework thin films: from fundamentals to applications. Chem Rev 2012, 112:1055-1083.
15. Kambe T., Sakamoto R., Hoshiko K., Takada K., Miyachi M., Ryu J.-H., et al. π-Conjugated nickel bis(dithiolene) complex nanosheet. J Am Chem Soc 2013, 135:2462-2465.
16. Bonifazi D., Mohnani S., Llanes-Pallas A. Supramolecular chemistry at interfaces: molecular recognition on nanopatterned porous surfaces. Chem Eur J 2009, 15:7004-7025.
17. Elemans J.A.A.W., Lei S.B., De Feyter S. Molecular and supramolecular networks on surfaces: from two-dimensional crystal engineering to reactivity. Angew Chem Int Ed 2009, 48:7298-7332.
18. Rabe J.P. Molecules at interfaces: STM in materials and life sciences. Ultramicroscopy 1992, 42-44:41-54.
19. 2. A systematic study of epitaxy and STM image contrast. Z Phys B 1994, 93:365-373.
20. Teyssandier J., Battaglini N., Seydou M., Anquetin G., Diawara B., Sun X., et al. Elaboration of hydrogen-bonded 2D supramolecular assemblies on Au(111) from solutions: toward naphthalene tetracarboxylic diimide-melamine nanoporous networks. J Phys Chem C 2013, 117:8737-8745.
21. Weiss P.S., Eigler D.M. Site dependence of the apparent shape of a molecule in scanning tunneling microscope images: benzene on Pt{111}. Phys Rev Lett 1993, 71:3139-3142.
22. 60 fullerite at 4.5K by scanning tunneling microscopy. Z Phys B 1993, 91:1-2.
23. 84 molecules on Si(111)-7×7 surfaces by scanning tunneling microscopy. Appl Surf Sci 2008, 254:7712-7717.
24. 6+2CO) surface. Phys Rev Lett 1988, 60:2398-2401.
25. Hallmark V.M., Chiang S., Brown J.K., Wöll Ch. Real-space imaging of the molecular organization of naphthalene on Pt(111). Phys Rev Lett 1991, 66:48-51.
26. Uemura S., Sakata M., Hirayama C., Kunitake M. Fullerene adlayers on various single-crystal metal surfaces prepared by transfer from L films. Langmuir 2004, 20:9198-9201.
27. Bertrand H., Guillot R., Teulade-Fichou M.-P., Fichou D. Synthesis, properties, and remarkable 2D self-assembly at the liquid/solid interface of a series of triskele-shaped 5,11,17-triazatrinaphthylenes (TrisK). Chem Eur J 2013, 19:312-317.
28. Uemura S., Tanoue R., Yilmaz N., Ohira A., Kunitake M. Molecular dynamics in two-dimensional supramolecular systems observed by STM. Materials 2010, 3:4252-4276.
29. Kunitake M., Akiba U., Batina N., Itaya K. Structures and dynamic processes of the formation of porphyrin adlayers on iodine-modified Au(111) in solution: in situ STM study. Langmuir 1997, 13:1607-1615.
30. Ohira A., Sakata M., Taniguchi I., Hirayama C., Kunitake M. Comparison of nanotube structures constructed from α-, β- and γ-cyclodextrins by potential-controlled adsorption. J Am Chem Soc 2003, 125:5057-5065.
31. Yoshimoto S., Itaya K. Adsorption and assembly of ions and organic molecules at electrochemical interfaces: nanoscale aspects. Annu Rev Anal Chem 2013, 6:213-235.
32. Ishikawa Y., Ohira A., Sakata M., Hirayama C., Kunitake M. A two-dimensional molecular network structure of trimesic acid prepared by adsorption-induced self-organization. Chem Commun 2002, 2652-2653.
33. Uemura S., Aono M., Komatsu T., Kunitake M. Two-dimensional self-assembled structures of melamine and melem at the aqueous solution-Au(111) interface. Langmuir 2011, 27:1336-1340.
34. Uemura S., Aono M., Sakata K., Komatsu T., Kunitake M. Thermodynamic control of 2D bicomponent porous networks of melamine and melem: diverse hydrogen-bonded networks. J Phys Chem C 2013, 117:24815-24821.
35. Tahara K., Lei S., Adisoejoso J., De Feyter S., Tobe Y. Supramolecular surface-confined architectures created by self-assembly of triangular phenylene-ethynylene macrocycles via van der Waals interaction. Chem Commun 2010, 46:8507-8525.
36. Lackinger M., Heckl W.M. Carboxylic acids: versatile building blocks and mediators for two-dimensional supramolecular self-assembly. Langmuir 2009, 25:11307-11321.
37. Lensen M.C., Elemans J.A.A.W., van Dingenen S.J.T., Gerritsen J.W., Speller S., Rowan A.E., et al. Giant porphyrin disks: control of their self-assembly at liquid-solid interfaces through metal-ligand interactions. Chem Eur J 2007, 13:7948-7956.
38. Grill L., Dyer M., Lafferentz L., Persson M., Peters M.V., Hecht S. Nano-architectures by covalent assembly of molecular building blocks. Nat Nanotechnol 2007, 2:687-691.
39. Matena M., Riehm T., Stöhr M., Jung T.A., Gade L.H. Transforming surface coordination polymers into covalent surface polymers: linked polycondensed aromatics through oligomerization of N-heterocyclic carbene intermediates. Angew Chem Int Ed 2008, 47:2414-2417.
40. Veld M.I., Iavicoli P., Haq S., Amabilino D.B., Raval R. Unique intermolecular reaction of simple porphyrins at a metal surface gives covalent nanostructures. Chem Commun 2008, 1536-1538.
41. Bieri M., Treier M., Cai J., Ait-Mansour K., Ruffieux P., Groning O., et al. Porous graphenes: two-dimensional polymer synthesis with atomic precision. Chem Commun 2009, 6919-6921.
42. Gutzler R., Walch H., Eder G., Kloft S., Heckl W.M., Lackinger M. Surface mediated synthesis of 2D covalent organic frameworks: 1,3,5-tris(4-bromophenyl)benzene on graphite(001), Cu(111), and Ag(110). Chem Commun 2009, 4456-4458.
43. Lipton-Duffin J.A., Ivasenko O., Perepichka D.F., Rosei F. Synthesis of polyphenylene molecular wires by surface-confined polymerization. Small 2009, 5:592-597.
44. Zwaneveld N.A.A., Pawlak R., Abel M., Catalin D., Gigmes D., Bertin D., et al. Organized formation of 2D extended covalent organic frameworks at surfaces. J Am Chem Soc 2008, 130:6678-6679.
45. Coratger R., Calmettes B., Abel M., Porte L. STM observations of the first polymerization steps between hexahydroxy-tri-phenylene and benzene-di-boronic acid molecules. Surf Sci 2011, 605:831-837.
46. Weigelt S., Bombis C., Busse C., Knudsen M.M., Gothelf K.V., Lægsgaard E., et al. Molecular self-assembly from building blocks synthesized on a surface in ultrahigh vacuum: kinetic control and topo-chemical reactions. ACS Nano 2008, 2:651-660.
47. Weigelt S., Busse C., Bombis C., Knudsen M.M., Gothelf K.V., Lægsgaard E., et al. Surface synthesis of 2D branched polymer nanostructures. Angew Chem Int Ed 2008, 47:4406-4410.
48. Cai J., Ruffieux P., Jaafar R., Bieri M., Braun T., Blankenburg S., et al. Atomically precise bottom-up fabrication of graphene nanoribbons. Nature 2010, 466:470-473.
49. Tanoue R., Higuchi R., Enoki N., Miyasato Y., Uemura S., Kimizuka N., et al. Thermodynamically controlled self-assembly of covalent nanoarchitectures in aqueous solution. ACS Nano 2011, 5:3923-3929.
50. Tanoue R., Higuchi R., Ikebe K., Uemura S., Kimizuka N., Stieg A.Z., et al. In situ STM investigation of aromatic poly(azomethine) arrays constructed by "on-site" equilibrium polymerization. Langmuir 2012, 28:13844-13851.
51. Tanoue R., Higuchi R., Ikebe K., Uemura S., Kimizuka N., Stieg A.Z., et al. Thermodynamic self-assembly of two-dimensional π-conjugated metal-porphyrin covalent organic frameworks by "on-site" equilibrium polymerization. J Nanosci Nanotechnol 2014, 3:2211-2216.
52. Tanoue R., Higuchi R., Ikebe K., Uemura S., Kimizuka N., Stieg A.Z., et al. Positional selectivity of reversible azomethine condensation reactions at solid/liquid interfaces leading to supramolecule formation. J Electroanal Chem Special Issue "In Honor of Kingo Itaya on His 65th Birthday" 2014, 716:145-149.
53. Kudernac T., Sändig N., Fernández Landaluce T., van Wees B.J., Rudolf P., Katsonis N., et al. Intermolecular repulsion through interfacial attraction: toward engineering of polymorphs. J Am Chem Soc 2009, 131:15655-15659.
54. Uribe-Romo F.J., Hunt J.R., Furukawa H., Klöck C., O'Keeffe M., Yaghi O.M. A crystalline imine-linked 3-D porous covalent organic framework. J Am Chem Soc 2009, 131:4570-4571.
55. Kunitake M., Deguchi Y., Kawatana K., Manabe O., Nakashima N. 'Interfacial Buffer Effect' of self-assembled monolayers of a carboxylic acid terminated alkanethiol on a gold electrode. J Chem Soc Chem Commun 1994, 563-564.
56. Okawa Y., Aono M. Materials science: nanoscale control of chain polymerization. Nature 2001, 409:683-684.
57. Sakaguchi H., Matsumura H., Gong H. Electrochemical epitaxial polymerization of single-molecular wires. Nat Mater 2004, 3:551-557.
58. Sakaguchi H., Matsumura H., Gong H., Abouelwafa A.M. Direct visualization of the formation of single-molecule conjugated copolymers. Science 2005, 310:1002-1006.
59. Higuchi R., Tanoue R., Enoki N., Miyasato Y., Sakaguchi K., Uemura S., et al. Chemical liquid deposition of aromatic poly(azomethine)s by spontaneous on-site polycondensation in aqueous solution. Chem Commun 2012, 48:3103-3105.
60. Alf M.E., Asatekin A., Barr M.C., Baxamusa S.H., Chelawat H., Ozaydin-lnce G., et al. Chemical vapor deposition of conformal, functional, and responsive polymer films. Adv Mater 2010, 22:1993-2027.
61. Schafer O., Greiner A., Pommerehne J., Guss W., Vestweber H., Tak H.Y., et al. Poly(p-phenylenevinylene) by chemical vapor deposition: synthesis, structural evaluation, glass transition, electroluminescence, and photoluminescence. Synth Met 1996, 82:1-9.
62. Zhou M., Heinze J. Electropolymerization of pyrrole and electrochemical study of polypyrrole: 1. Evidence for structural diversity of polypyrrole. Electrochim Acta 1999, 44:1733-1748.
63. Roncali J. Conjugated poly(thiophenes): synthesis, functionalization, and applications. Chem Rev 1992, 92:711-738.
64. Higuchi R., Tanoue R., Sakaguchi K., Yanai K., Uemura S., Kunitake M. Vertically standing nanowalls of pristine poly(azomethine) on a graphite by chemical liquid deposition. Polymer 2013, 54:3452-3457.
65. Kimura K., Zhuang J.H., Shirabe K., Yamashita Y. Preparation of needle-like poly(azomethine) crystals by means of reaction-induced crystallization of oligomers. Polymer 2003, 44:4761-4764.
66. Yan Y., Chen L., Dai H., Chen Z., Li X., Liu X. Morphosynthesis of nanostructured polyazomethines and carbon through constitutional dynamic chemistry controlled reaction induced crystallization process. Polymer 2012, 53:1611-1616.
67. Wang C., Shieh S., LeGoff E., Kanatzidis M.G. Synthesis and characterization of a new conjugated aromatic poly(azomethine) derivative based on the 3',4'-Dibutyl-α-terthiophene building block. Macromolecules 1996, 29:3147-3156.
68. Lee T.S., Kim J., Kumar J., Tripathy S. Synthesis and self-assembled multilayer thin film formation of water-soluble conjugated aromatic polyimines. Macromol Chem Phys 1998, 199:1445-1450.