TY - JOUR
T1 - Visualization of various supramolecular assemblies of oligo(para- phenylenevinylene)-melamine and perylene bisimide
AU - Hoeben, F.J.M.
AU - Zhang, Jian
AU - Lee, C.C.
AU - Pouderoijen, M.J.
AU - Wolffs, M.
AU - Würthner, F.
AU - Schenning, A.P.H.J.
AU - Meijer, E.W.
AU - Feyter, de, S.
PY - 2008
Y1 - 2008
N2 - 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 hydrogenbonded 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 tempera-ture. Complementary hydrogen bonding to a perylene bisimide derivative in an apolar solvent yields multicomponent, Ï€-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. -© 2008 Wiley-VCH Verlag GmbH & Co. KGaA
AB - 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 hydrogenbonded 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 tempera-ture. Complementary hydrogen bonding to a perylene bisimide derivative in an apolar solvent yields multicomponent, Ï€-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. -© 2008 Wiley-VCH Verlag GmbH & Co. KGaA
U2 - 10.1002/chem.200800760
DO - 10.1002/chem.200800760
M3 - Article
C2 - 18671309
VL - 14
SP - 8579
EP - 8589
JO - Chemistry : A European Journal
JF - Chemistry : A European Journal
SN - 0947-6539
IS - 28
ER -