Effect of the ortho alkylation of perylene bisimides on the alignment and self-assembly properties.
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The effect of the ortho alkylation of perylene bisimides on the alignment and self-assembly properties has been studied.Furthermore, a solvent-induced growth of ultralong organic n-type semiconducting fibrils from non-ortho-alkylated perylene bisimide was observed.Ortho substitution of the perylene bisimide core alters the mode of fibrillar growth, leading to isotropic crystallization.
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Affiliation: Laboratory of Functional Organic Materials and Devices, Eindhoven University of Technology P.O. Box 513, 5600 MB, Eindhoven (The Netherlands) E-mail: a.p.h.j.schenning@tue.nl.
ABSTRACT
The effect of the ortho alkylation of perylene bisimides on the alignment and self-assembly properties has been studied. It was found that the dichroic properties of perylene bisimides in a liquid crystal host can be reversed with a single synthetic step by ortho alkylation. Furthermore, a solvent-induced growth of ultralong organic n-type semiconducting fibrils from non-ortho-alkylated perylene bisimide was observed. Ortho substitution of the perylene bisimide core alters the mode of fibrillar growth, leading to isotropic crystallization. No MeSH data available. |
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fig04: Photographs of perylene bisimide dodecane solutions (5 mm) at the indicated temperatures taken under normal light for PB-2 (top) and PB-1 (bottom). Mentions: It was also observed that in a 5 mm solution in dodecane, PB-2 is completely soluble at 140 οC and that aggregates start to appear upon quenching to 20 οC (Figure 4, top). Unlike PB-2, PB-1 does not seem to dissolve completely in dodecane, even at elevated temperature (approx. 160 οC), as the dispersion lacks transparency (Figure 4, bottom). Most likely a small fraction of associated perylene bisimide nanocrystals act as seeds to nucleate the unidirectional growth of ultralong fibers. As earlier reported, most likely so-called H-type aggregates are formed in which the fluorescence is quenched.14 |
View Article: PubMed Central - PubMed
Affiliation: Laboratory of Functional Organic Materials and Devices, Eindhoven University of Technology P.O. Box 513, 5600 MB, Eindhoven (The Netherlands) E-mail: a.p.h.j.schenning@tue.nl.
No MeSH data available.