Soluble Graphene Nanoribbons from Planarization of Oligophenylenes

被引:4
作者
Sen, Choong Ping [1 ]
Valiyaveettil, Suresh [1 ]
机构
[1] Natl Univ Singapore, Fac Sci, Dept Chem, 3 Sci Dr 2, Singapore 117543, Singapore
关键词
cyclodehydrogenation; graphene; nanoribbons; oligophenylenes; self-assembly; BOTTOM-UP SYNTHESIS; REARRANGEMENTS; SPECTROSCOPY;
D O I
10.1002/chem.201604778
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A solution-based chemical synthesis of two gra-phene nanoribbons with armchair edges is reported. The precursor oligophenylene molecules are synthesized and subjected to oxidative cyclodehydrogenation to afford the target molecules, G-1 and G-2. These molecules have good solubility in organic solvents, and show a large redshift in their absorption edge (up to 185 nm) and emission maximum (up to 125 nm) after planarization. Fibrous structures are formed upon self-assembly of molecules through columnar pi-pi stacking. Such molecular assemblies may be useful for various applications.
引用
收藏
页码:1686 / 1693
页数:8
相关论文
共 37 条
  • [1] Bonaccorso F, 2010, NAT PHOTONICS, V4, P611, DOI [10.1038/NPHOTON.2010.186, 10.1038/nphoton.2010.186]
  • [2] Biaryl synthesis via Suzuki coupling promoted by catalytic amounts of quaternary ammonium salts
    Castanet, AS
    Colobert, F
    Desmurs, JR
    Schlama, T
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 182 (01) : 481 - 487
  • [3] Chen L., 2012, Angew. Chem. Int. Ed, V124, P7758
  • [4] From Nanographene and Graphene Nanoribbons to Graphene Sheets: Chemical Synthesis
    Chen, Long
    Hernandez, Yenny
    Feng, Xinliang
    Muellen, Klaus
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (31) : 7640 - 7654
  • [5] Chen YC, 2015, NAT NANOTECHNOL, V10, P156, DOI [10.1038/NNANO.2014.307, 10.1038/nnano.2014.307]
  • [6] BENZOLOGUES OF PERYLENE CORONENE + ANTHANTHRENE
    CLAR, E
    MCCALLUM, A
    [J]. TETRAHEDRON, 1964, 20 (03) : 507 - &
  • [7] Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore-rational design of potentially useful bioimaging fluorescence probe
    Gabe, Y
    Urano, Y
    Kikuchi, K
    Kojima, H
    Nagano, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) : 3357 - 3367
  • [8] Grzybowski M., 2013, ANGEW CHEM, V125, P10084
  • [9] Comparison of Oxidative Aromatic Coupling and the Scholl Reaction
    Grzybowski, Marek
    Skonieczny, Kamil
    Butenschoen, Holger
    Gryko, Daniel T.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) : 9900 - 9930
  • [10] Tetrabenzanthanthrenes by mitigation of rearrangements in the planarization of ortho-phenylene hexamers
    He, Jian
    Mathew, Sanyo
    Kinney, Zacharias J.
    Warrell, Rachel M.
    Molina, James S.
    Hartley, C. Scott
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (33) : 7245 - 7248