%0 Journal Article %1 C1SC00435B %A Dehm, Volker %A Buchner, Michael %A Seibt, Joachim %A Engel, Volker %A Wurthner, Frank %D 2011 %I The Royal Society of Chemistry %J Chem. Sci. %K ak-engel %N 11 %P 2094-2100 %R 10.1039/C1SC00435B %T Foldamer with a spiral perylene bisimide staircase aggregate structure %U http://dx.doi.org/10.1039/C1SC00435B %V 2 %X Although the precise control of dye-dye interactions is known to be of fundamental importance to achieve desired functional properties in small pi-conjugated materials, there are only sporadic examples where precise structural control of dye-dye interactions could be achieved by the attachment of the chromophores to an oligomeric or polymeric backbone. In this edge article, we introduce an oligophenylene ethynylene/perylene bisimide (PBI) dye system which is conceived by the foldamer concept. The molecular design enables folding of the small pi-conjugated oligomer to give a geometrically well-defined small pi-stack of intrastrand PBI molecules. The synthesis of the foldamer and its characterization by MALDI-TOF mass spectrometry are described, and the average size is estimated by gel permeation chromatography (GPC) and diffusion ordered NMR spectroscopy (DOSY). The folding dynamics are demonstrated by ultraviolet/visible absorption and fluorescence emission spectroscopic studies as the folded and unfolded states possess distinct optical properties. Quantum dynamic considerations revealed a good agreement of the calculated aggregate absorption spectrum with those obtained experimentally.

@article{C1SC00435B, abstract = {Although the precise control of dye-dye interactions is known to be of fundamental importance to achieve desired functional properties in [small pi]-conjugated materials{,} there are only sporadic examples where precise structural control of dye-dye interactions could be achieved by the attachment of the chromophores to an oligomeric or polymeric backbone. In this edge article{,} we introduce an oligophenylene ethynylene/perylene bisimide (PBI) dye system which is conceived by the foldamer concept. The molecular design enables folding of the [small pi]-conjugated oligomer to give a geometrically well-defined [small pi]-stack of intrastrand PBI molecules. The synthesis of the foldamer and its characterization by MALDI-TOF mass spectrometry are described{,} and the average size is estimated by gel permeation chromatography (GPC) and diffusion ordered NMR spectroscopy (DOSY). The folding dynamics are demonstrated by ultraviolet/visible absorption and fluorescence emission spectroscopic studies as the folded and unfolded states possess distinct optical properties. Quantum dynamic considerations revealed a good agreement of the calculated aggregate absorption spectrum with those obtained experimentally.}, added-at = {2017-06-20T16:17:41.000+0200}, author = {Dehm, Volker and Buchner, Michael and Seibt, Joachim and Engel, Volker and Wurthner, Frank}, biburl = {https://www.bibsonomy.org/bibtex/22707ecd1d3e60d40c3f9bc67fdf84f42/ak-engel-uniwue}, description = {Foldamer with a spiral perylene bisimide staircase aggregate structure - Chemical Science (RSC Publishing)}, doi = {10.1039/C1SC00435B}, interhash = {d285becaff41e889303c76df97885316}, intrahash = {2707ecd1d3e60d40c3f9bc67fdf84f42}, journal = {Chem. Sci.}, keywords = {ak-engel}, number = 11, pages = {2094-2100}, publisher = {The Royal Society of Chemistry}, timestamp = {2017-06-20T16:17:41.000+0200}, title = {Foldamer with a spiral perylene bisimide staircase aggregate structure}, url = {http://dx.doi.org/10.1039/C1SC00435B}, volume = 2, year = 2011 }