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.
Würthner
Frank
F
Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany. wuerthner@chemie.uni-wuerzburg.de
Chen
Zhijian
Z
Hoeben
Freek J M
FJ
Osswald
Peter
P
You
Chang-Cheng
CC
Jonkheijm
Pascal
P
Herrikhuyzen
Jeroen V
JV
Schenning
Albertus P H J
AP
van der Schoot
Paul P A M
PP
Meijer
E W
EW
Beckers
Edwin H A
EH
Meskers
Stefan C J
SC
Janssen
René A J
RA