Supramolecular p-n-heterojunctions by co-self-organization of oligo(p-phenylene vinylene) and perylene bisimide dyes.
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.
Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany. wuerthner@chemie.uni-wuerzburg.de
Frank
F
Würthner
Zhijian
Z
Chen
Freek J M
FJ
Hoeben
Peter
P
Osswald
Chang-Cheng
CC
You
Pascal
P
Jonkheijm
Jeroen V
JV
Herrikhuyzen
Albertus P H J
AP
Schenning
Paul P A M
PP
van der Schoot
E W
EW
Meijer
Edwin H A
EH
Beckers
Stefan C J
SC
Meskers
René A J
RA
Janssen