Supramolecular p-n-heterojunctions by co-self-organization of oligo(p-phenylene vinylene) and perylene bisimide dyes |
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Authors: | Würthner Frank Chen Zhijian Hoeben Freek J M Osswald Peter You Chang-Cheng Jonkheijm Pascal Herrikhuyzen Jeroen V Schenning Albertus P H J van der Schoot Paul P A M Meijer E W Beckers Edwin H A Meskers Stefan C J Janssen René A J |
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Institution: | Institut für Organische Chemie, Universit?t Würzburg, Am Hubland, D-97074 Würzburg, Germany. wuerthner@chemie.uni-wuerzburg.de |
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Abstract: | Comparative studies on hydrogen-bonded versus covalently linked donor-acceptor-donor dye arrays obtained from oligo(p-phenylene vinylene)s (OPVs) as donor and bay-substituted perylene bisimides (PERYs) as acceptor dyes are presented. Both systems form well-ordered J-type aggregates in methylcyclohexane, but only hydrogen-bonded arrays afford hierarchically assembled chiral OPV-PERY dye superstructures consisting of left-handed helical pi-pi co-aggregates (CD spectroscopy) of the two dyes that further assemble into right-handed nanometer-scale supercoils in the solid state (AFM study). In the case of hydrogen-bonded arrays, the stability of the aggregates in solution increases with increasing conjugation length of the OPV unit. The well-defined co-aggregated dyes presented here exhibit photoinduced electron transfer on subpicosecond time scale, and thus, these supramolecular entities might serve as valuable nanoscopic functional units. |
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