A photofunctional bottom-up bis(dipyrrinato)zinc(II) complex nanosheet

Nature Communications

Volumn 6, Issue , 2015, Pages

  Sakamoto, Ryota ^a   Hoshiko, Ken ^a   Liu, Qian ^b   Yagi, Toshiki ^a   Nagayama, Tatsuhiro ^a   Kusaka, Shinpei ^a   Tsuchiya, Mizuho ^a   Kitagawa, Yasutaka ^c   Wong, Wai Yeung ^b   Nishihara, Hiroshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

^c OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIS(DIPYRRINATO)ZINC(II) COMPLEX; GRAPHENE; LIGAND; NANOPARTICLE; NANOSHEET; TIN OXIDE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ELECTRODE; MOLECULAR ANALYSIS; NANOTECHNOLOGY; PHOTOCHEMISTRY; TWO-DIMENSIONAL MODELING;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONTROLLED STUDY; ELECTRODE; LIQUID; PARTICLE SIZE; SCANNING TUNNELING MICROSCOPY; SYNTHESIS; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 84926329843     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms7713     Document Type: Article

References (61)

1. Novoselov, K. S. et al. Electric field effect in atomically thin carbon films. Science 306, 666-669 (2004).
2. Geim, A. K. & Novoselov, K. S. The rise of graphene. Nat. Mater. 6, 183-191 (2007).
3. Lin, Y.-M. et al. 100-GHz transistors from wafer-scale epitaxial graphene. Science 327, 662 (2010).
4. Bonaccorso, F., Sun, Z., Hasan, T. & Ferrari, A. C. Graphene photonics and optoelectronics. Nat. Photonics 4, 611-622 (2010).
5. Son, Y.-W., Cohen, M. L. & Louie, S. G. Half-metallic graphene nanoribbons. Nature 444, 347-349 (2006).
6. Maassen, J., Ji, W. & Guo, H. Graphene spintronics: the role of ferromagnetic electrodes. Nano Lett. 11, 151-155 (2011).
7. Sasaki, T., Watanabe, M., Hashizume, H., Yamada, H. & Nakazawa, H. Macromolecule-like aspects for a colloidal suspension of an exfoliated titanate. Pairwise association of nanosheets and dynamic reassembling process initiated from it. J. Am. Chem. Soc. 118, 8329-8335 (1996).
8. Li, B.-W. et al. Engineered interfaces of artificial perovskite oxide superlattices via nanosheet deposition process. ACS Nano 4, 6673-6680 (2010).
9. Umar, A. & Hahn, Y. B. ZnO nanosheet networks and hexagonal nanodiscs grown on silicon substrate: growth mechanism and structural and optical properties. Nanotechnology 17, 2174-2180 (2006).
10. Sakai, N., Ebina, Y., Takada, K. & Sasaki, T. Electronic band structure of titania semiconductor nanosheets revealed by electrochemical and photoelectrochemical studies. J. Am. Chem. Soc. 126, 5851-5858 (2004).
11. Muramatu, M. et al. Fabrication of densely packed titania nanosheet films on solid surface by use of Langmuir-Blodgett deposition method without amphiphilic additives. Langmuir 21, 6590-6595 (2005).
12. Coleman, J. N. et al. Two-dimensional nanosheets produced by liquid exfoliation of layered materials. Science 331, 568-571 (2011).
13. Splendiani, A. et al. Emerging photoluminescence in monolayer MoS2. Nano Lett. 10, 1271-1275 (2010).
14. Lee, H. S. et al. MoS2 nanosheets for top-gate nonvolatile memory transistor channel. Small 8, 3111-3115 (2012).
15. Zeng, Z. et al. Single-layer semiconducting nanosheets: high-yield preparation and device fabrication. Angew. Chem. Int. Ed. 50, 11093-11097 (2011).
16. Ma, R., Liu, Z., Li, L., Iyi, N. & Sasaki, T. Exfoliating layered double hydroxides in formamide: a method to obtain positively charged nanosheets. J. Mater. Chem. 16, 3809-3813 (2006).
17. Ma, R. et al. Synthesis and exfoliation of Co2+-Fe3+ layered double hydroxides: an innovative topochemical approach. J. Am. Chem. Soc. 129, 5257-5263 (2007).
18. Ida, S., Shiga, D., Koinuma, M. & Matsumoto, Y. Synthesis of hexagonal nickel hydroxide nanosheets by exfoliation of layered nickel hydroxide intercalated with dodecyl sulfate ions. J. Am. Chem. Soc. 130, 14038-14039 (2008).
19. Yan, D. et al. Ordered poly(p-phenylene)/layered double hydroxide ultrathin films with blue luminescence by layer-by-layer assembly. Angew. Chem. Int. Ed. 48, 3073-3076 (2009).
20. Yan, D. et al. Reversibly thermochromic, fluorescent ultrathin films with a supramolecular architecture. Angew. Chem. Int. Ed. 50, 720-723 (2011).
21. Sakamoto, J., van Heijst, J., Lukin, O. & Schlüter, A. D. Two-dimensional polymers: just a dream of synthetic chemists? Angew. Chem. Int. Ed. 48, 1030-1069 (2009).
22. Kissel, P. et al. A two-dimensional polymer prepared by organic synthesis. Nat. Chem 4, 287-291 (2012).
23. Payamyar, P. et al. Synthesis of a covalent monolayer sheet by photochemical anthracene dimerization at the air/water interface and its mechanical characterization by AFM indentation. Adv. Mater. 26, 2052-2058 (2014).
24. Kory, M. J. et al. Gram-scale synthesis of two-dimensional polymer crystals and their structure analysis by X-ray diffraction. Nat. Chem. 6, 779-784 (2014).
25. Kissel, P., Murray, D. J., Wulftange, W. J., Catalano, V. J. & King, B. T. A nanoporous two-dimensional polymer by single-crystal-to-single-crystal photopolymerization. Nat. Chem. 6, 774-778 (2014).
26. Bauer, T. et al. Synthesis of free standing, monolayered organometallic sheets at the air/water interface. Angew. Chem. Int. Ed. 50, 7879-7884 (2011).
27. Zheng, Z. et al. Synthesis of two-dimensional analogues of copolymers by site-to- site transmetalation of organometallic monolayer sheets. J. Am. Chem. Soc. 136, 6103-6110 (2014).
28. Schrettl, S. et al. Functional carbon nanosheets prepared from hexayne amphiphile monolayers at room temperature. Nat. Chem. 6, 468-476 (2014).
29. Makiura, R. et al. Surface nano-architecture of a metal-organic framework. Nat. Mater. 9, 565-571 (2010).
30. Motoyama, S., Makiura, R., Sakata, O. & Kitagawa, H. Highly crystalline nanofilm by layering of porphyrin metal-organic framework sheets. J. Am. Chem. Soc. 133, 5640-5643 (2011).
31. Zwaneveld, N. A. A. et al. Organized formation of 2D extended covalent organic frameworks at surfaces. J. Am. Chem. Soc. 130, 6678-6679 (2008).
32. Tanoue, R. et al. Thermodynamically controlled self-assembly of covalent nanoarchitectures in aqueous solution. ACS Nano 5, 3923-3929 (2011).
33. Dienstmaier, J. F. et al. Synthesis of well-ordered COF monolayers: surface growth of nanocrystalline precursors versus direct on-surface polycondensation. ACS Nano 5, 9737-9745 (2011).
34. Liu, X.-H. et al. On-surface synthesis of single-layered two-dimensional covalent organic frameworks via solid-vapor interface reactions. J. Am. Chem. Soc. 135, 10470-10474 (2013).
35. Grill, L. et al. Nano-architectures by covalent assembly of molecular building blocks. Nat. Nanotech. 2, 687-691 (2007).
36. Gutzler, R. et al. 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. 4456-4458 (2009).
37. Abel, M., Clair, S., Ourdjini, O., Mossayan, M. & Porte, L. Single-layer of polymeric Fe-phthalocyanine: an organometallic sheet on metal and thin insulating film. J. Am. Chem. Soc. 133, 1203-1205 (2011).
38. Li, Y. et al. Coordination and metalation bifunctionality of Cu with 5,10,15,20-tetra(4-pyridyl)porphyrin: toward a mixed-valence two-dimensional coordination network. J. Am. Chem. Soc. 134, 6401-6408 (2012).
39. Sirtl, T. et al. Control of intermolecular bonds by deposition rates at room temperature: hydrogen bonds versus metal coordination in trinitrile monolayers. J. Am. Chem. Soc. 135, 691-695 (2013).
40. Berlanga, I. et al. Delamination of layered covalent organic frameworks. Small 7, 1207-1211 (2011).
41. Berlanga, I., Rubén, M.-B. & Zamora, F. Tuning delamination of layered covalent organic frameworks through structural design. Chem. Commun. 48, 7976-7978 (2012).
42. Bunck, D. N. & Dichtel, W. R. Bulk synthesis of exfoliated two-dimensional polymers using hydrazone-linked covalent organic frameworks. J. Am. Chem. Soc. 135, 14952-14955 (2013).
43. Amo-Ochoa, P. et al. Single layers of a multifunctional laminar Cu(I,II) coordination polymer. Chem. Commun. 46, 3262-3264 (2010).
44. Li, P.-Z., Maeda, Y. & Xu, Q. Top-down fabrication of crystalline metal-organic framework nanosheet. Chem. Commun. 47, 8436-8438 (2011).
45. Tan, J.-C., Saines, P. J., Bithell, E. G. & Cheetham, A. K. Hybrid nanosheets of an inorganic-organic framework material: facile synthesis, structure, and elastic properties. ACS Nano 6, 615-621 (2012).
46. Xu, G., Yamada, T., Otsubo, K., Sakaida, S. & Kitagawa, H. Facile 'modular assembly' for fast construction of a highly oriented crystalline MOF nanofilm. J. Am. Chem. Soc. 134, 16524-16527 (2012).
47. Kambe, T. et al. π-conjugated nickel bisdithiolene complex nanosheet. J. Am. Chem. Soc. 135, 2462-2465 (2013).
48. Hoshiko, K., Kambe, T., Sakamoto, R., Takada, K. & Nishihara, H. Fabrication of dense and multi-layered films of the nickel bis(dithiolene) nanosheet by means of the Langmuir-Schäfer method. Chem. Lett. 43, 252-253 (2014).
49. Kambe, T. et al. Redox control and high conductivity of nickel bis(dithiolene) complex p-nanosheet: A potential organic two-dimensional topological insulator. J. Am. Chem. Soc. 136, 14357-14360 (2014).
50. Wood, T. E. & Thompson, A. Advances in the chemistry of dipyrrins and their complexes. Chem. Rev. 107, 1831-1861 (2007).
51. Maeda, H. et al. Nanoscale spherical architectures fabricated by metal coordination of multiple dipyrrin moieties. J. Am. Chem. Soc. 128, 10024-10025 (2006).
52. Sazanovich, I. V. et al. Structural control of the excited-state dynamics of bis(dipyrrinato)zinc complexes: self-assembling chromophores for lightharvesting architectures. J. Am. Chem. Soc. 126, 2664-2665 (2004).
53. Kusaka, S., Sakamoto, R., Kitagawa, Y., Okumura, M. & Nishihara, H. An extremely bright heteroleptic bis(dipyrrinato)zinc(II) complex. Chem. Asian J. 7, 907-910 (2012).
54. Tsuchiya, M. et al. Asymmetric dinuclear bis(dipyrrinato)zinc(II) complexes: Broad absorption and unidirectional quantitative exciton transmission. Chem. Commun. 50, 5881-5883 (2014).
55. Karweik, D. H. & Winograd, N. Nitrogen charge distributions in free-base porphyrins, metalloporphyrins, and their reduced analogs observed by X-ray photoelectron spectroscopy. Inorg. Chem. 15, 2336-2342 (1976).
56. Wang, Z. et al. Phenanthro[9,10-d]imidazole as a new building block for blue light emitting materials. J. Mater. Chem. 21, 5451-5456 (2011).
57. Micheal, M.-C. L. & Gregory, C. F. Cu(I)/bis(azaferrocene)-catalyzed enantioselective synthesis of b-lactams via couplings of alkynes with nitrones. J. Am. Chem. Soc. 124, 4572-4573 (2002).
58. Qin, W., Baruah, M., Van der Auweraer, M., De Schryver, F. C. & Boens, N. Photophysical properties of borondipyrromethene analogues in solution. J. Phys. Chem. A 109, 7371-7384 (2005).
59. Spitler, E. L. & Dichtel, W. R. Lewis acid-catalysed formation of two dimensional phthalocyanine covalent organic frameworks. Nat. Chem. 2, 672-677 (2010).
60. Ping, J. & Fuhrer, M. S. Layer number and stacking sequence imaging of fewlayer graphene by transmission electron microscopy. Nano Lett. 12, 4635-4641 (2012).
61. Nagaoka, S., Horiuchi, K., Shikishima, M. & Nakajima, A. Physical properties of aliphatic monolayer on indium-tin oxide and SnO2(110) relevant to thermal stability of soft-landed Cr(benzene)2. J. Phys. Chem. C 115, 24215-24220 (2011).