Multicolour Self-Assembled Fluorene Co-Oligomers: From Molecules to the Solid State via White-Light-Emitting Organogels

被引:95
作者
Abbel, Robert [1 ]
van der Weegen, Rob [1 ]
Pisula, Wojciech [2 ]
Surin, Mathieu [3 ]
Leclere, Philippe [1 ,3 ]
Lazzaroni, Roberto [3 ]
Meijer, E. W. [1 ]
Schenning, Albertus P. H. J. [1 ]
机构
[1] Eindhoven Univ Technol, Lab Organ & Macromol Chem, NL-5600 MB Eindhoven, Netherlands
[2] Max Planck Inst Polymer Res, D-55128 Mainz, Germany
[3] Univ Mons, B-7000 Mons, Belgium
关键词
energy transfer; fluorene; gels; liquid crystals; self-assembly; PI-CONJUGATED OLIGOMERS; ORGANIC SEMICONDUCTORS; FLUORESCENT ORGANOGELS; OPTICAL-PROPERTIES; CHARGE-TRANSPORT; ENERGY-TRANSFER; POLYCATENAR MESOGENS; LIQUID-CRYSTALS; COPOLYMERS; POLYMERS;
D O I
10.1002/chem.200900620
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Five fluorene-based co-oligomers have been prepared to study their self-assembly in a wide range of concentrations, from dilute solutions to the solid state. Subtle changes to the chemical structures, introduced to tune the emission colours over the entire visible range, induce strong differences in aggregation behaviour. Only two of the fluorescent co-oligomer derivatives self-assemble to form soluble fibrils from which fluorescent organogels emerge at higher concentrations. In contrast, the other compounds form precipitates. Mixed fluorescent co-oligomer systems exhibit partial energy transfer, which allows the creation of white-light-emitting gels. Finally, a mechanism for the hierarchical self-assembly of this class of materials is proposed based on experimental results and molecular modelling calculations.
引用
收藏
页码:9737 / 9746
页数:10
相关论文
共 76 条
[31]   Self-assembled nanotapes of oligo(p-phenylene vinylene)s:: Sol-gel controlled optical properties in fluorescent π-electronic gels [J].
George, SJ ;
Ajayaghosh, A .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (11) :3217-3227
[32]   Polycatenar liquid crystals with long rigid aromatic cores:: a review of recent works [J].
Gharbia, M ;
Gharbi, A ;
Nguyen, HT ;
Malthête, J .
CURRENT OPINION IN COLLOID & INTERFACE SCIENCE, 2002, 7 (5-6) :312-325
[33]   Polar order in columnar phase made of polycatenar bent-core molecules [J].
Gorecka, E ;
Pociecha, D ;
Matraszek, J ;
Mieczkowski, J ;
Shimbo, Y ;
Takanishi, Y ;
Takezoe, H .
PHYSICAL REVIEW E, 2006, 73 (03)
[34]   Vibrational characterization of the peptide bond [J].
Herrebout, W ;
Clou, K ;
Desseyn, HO ;
Blaton, N .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2003, 59 (01) :47-59
[35]   Low-molecular-weight gelators: Elucidating the principles of gelation based on gelator solubility and a cooperative self-assembly model [J].
Hirst, Andrew R. ;
Coates, Ian A. ;
Boucheteau, Thomas R. ;
Miravet, Juan F. ;
Escuder, Beatriu ;
Castelletto, Valeria ;
Hamley, Ian W. ;
Smith, David K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) :9113-9121
[36]   Origin of the broken conjugation in m-phenylene linked conjugated polymers [J].
Hong, SY ;
Kim, DY ;
Kim, CY ;
Hoffmann, R .
MACROMOLECULES, 2001, 34 (18) :6474-6481
[37]   Fluorene homopolymers and copolymers [J].
Inbasekaran, M ;
Woo, E ;
Wu, WS ;
Bernius, M ;
Wujkowski, L .
SYNTHETIC METALS, 2000, 111 :397-401
[38]   Molecular organogel-forming porphyrin derivative with hydrophobic L-glutamide [J].
Jintoku, Hirokuni ;
Sagawa, Takashi ;
Sawada, Tsuyoshi ;
Takafuji, Makoto ;
Hachisako, Hiroshi ;
Ihara, Hirotaka .
TETRAHEDRON LETTERS, 2008, 49 (25) :3987-3990
[39]   Color-tunable fluorescent organogels: Columnar self-assembly of pyrene-containing oligo(glutamic acid)s [J].
Kamikawa, Yuko ;
Kato, Takashi .
LANGMUIR, 2007, 23 (01) :274-278
[40]   Thieno[3,4-b]pyrazines:: Synthesis, structure, and reactivity [J].
Kenning, DD ;
Mitchell, KA ;
Calhoun, TR ;
Funfar, MR ;
Sattler, DJ ;
Rasmussen, SC .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :9073-9076