Visualization of Various Supramolecular Assemblies of Oligo(para-phenylenevinylene)-Melamine and Perylene Bisimide

被引:43
作者
Hoeben, Freek J. M. [1 ]
Zhang, Jian [2 ]
Lee, Cameron C. [1 ]
Pouderoijen, Maarten J. [1 ]
Wolffs, Martin [1 ]
Wuerthner, Frank [3 ]
Schenning, Albertus P. H. J. [1 ]
Meijer, E. W. [1 ]
De Feyter, Steven [2 ]
机构
[1] Eindhoven Univ Technol, Lab Macromol & Organ Chem, NL-5600 MB Eindhoven, Netherlands
[2] Katholieke Univ Leuven, Inst Nanoscale Phys & Chem, Lab Photochem & Spect, B-3001 Louvain, Belgium
[3] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
关键词
chirality; donor-acceptor systems; hydrogen bonds; scanning probe microscopy; self-assembly;
D O I
10.1002/chem.200800760
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A melamine derivative has been covalently equipped with two oligo(para-phenylenevinylene) (OPV) chromophores. This procedure yields a bifunctional molecule with two hydrogen-bonding arrays available for complementary binding, to perylene bisimide derivatives. Depending on the solvent. hydrogen-bonded trimers, tetramers. and dimers on a graphite surface are observed for pure OPV-melamine by using scanning tunneling microscopy (STM). Upon the addition of perylene bisimide. linear tapes of perylene bisimide. 12-membered rosettes that consist of alternating hydrogen-bonded OPV-melamine and perylene bisimide moieties are visualized. These results provide direct evidence for the possible modes of hydrogen bonding within a supramolecular co-assembly in solution. Subsequently, the optical properties of pure OPV-melamine and co-assemblies with a perylene bisimide derivative were characterized in solution. In an apolar solvent, OPV-melamine self-assembles into chiral superstructures. Disassembly into molecularly dissolved species is reversibly controlled by concentration and temperature. Complementary hydrogen bonding to a perylene bisimide derivative in an apolar solvent yields multicomponent, pi-stacked dye assemblies of enhanced stability that are characterized by fluorescence quenching of the constituent chromophores. Titration experiments reveal that a mixture of hydrogen-bonded oligomers is present in solution, rather than a single discrete assembly. The solution experiments are consistent with the STM results, which revealed various supramolecular assemblies. Our system is likely not to be optimally programmed to obtain a discrete co-assembled structure in quantitative yield.
引用
收藏
页码:8579 / 8589
页数:11
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