Supramolecular p-n-heterojunctions by co-self-organization of oligo(p-phenylene vinylene) and perylene bisimide dyes

被引:383
作者
Würthner, F
Chen, ZJ
Hoeben, FJM
Osswald, P
You, CC
Jonkheijm, P
von Herrikhuyzen, J
Schenning, APHJ
van der Schoot, PPAM
Meijer, EW
Beckers, EHA
Meskers, SCJ
Janssen, RAJ
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Eindhoven Univ Technol, Lab Macromol & Organ Chem, NL-5600 MB Eindhoven, Netherlands
[3] Eindhoven Univ Technol, Dept Appl Phys, NL-5600 MB Eindhoven, Netherlands
关键词
D O I
10.1021/ja0475353
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:10611 / 10618
页数:8
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