Perylene bisimides

Mikroyannidis JA, Stylianakis MM, Sharma GD, Balraju P, Roy MS (2009) A novel alternating phenylenevinylene copolymer with perylene bisimide units synthesis, photophysical, electrochemical, and photovoltaic properties. J Phys Chem C113 7904-7912... 

Li C, Mishchenko A, Li Z, Pobelov I, Wandlowski T, Li XQ, Wurthner F, Bagrets A, Evers F (2008) Electrochemical gate-controlled electron transport of redox-active single perylene bisimide molecular junctions. J Phys Condens Matter 20 374122... 

Chemically Controlled Conductance of Perylene Bisimide Derivatives. 167... 

Perylene bisimide-dithienothiophene derivatives have been prepared (09JPC(A)5039). A femtosecond transient absorption study showed the presence of two positive bands at 490 nm (perylene cation radical) and at 730 nm (perylene anion radical). 

Dyes can also be incorporated into hydrogen-bonded superstructures using the complementarity of the hydrogen bond donors and acceptors. The addition of a perylene bisimide dye to chiral dialkyl melamine derivatives leads to aggregates (Fig. 26) which show induced circular dichroism in the dye part of the assembly in methylcyclohexane as well as the formation of mesoscopic fibres when the solvent is evaporated [227]. The melamine compounds... 

Similarly, a turbidity assay can be used to monitor the formation of cross-linked complexes in real time. Recently, Xiao-Liu Li et al. used Lac-functionalized perylene bisimide (PBI-Lac) to form a right-handed supramolecular stacking induced by the chiral Lac moieties. In the turbidity assay, the PNA lectin was applied to investigate the formation of three-dimensional chiral aggregates [48], Upon addition of PBI-Lac... 

An extreme case in the difference between PL and EL spectra is presented in Fig. 116. A perylene bisimide pigment (PBP)-doped TPD layer reveals the PL spectrum belonging totally to the violet emission of TPD molecules, and EL spectrum originating from radiative transitions of the doped... 

Linearly arranged perylene bisimides [14] can be synthesized according to the reaction sequence of Scheme 1 where the starting material 1 was prepared from the technical perylene bisanhydride 5 and primary amines. 

Figure 1.6. Molecular structure of a bichromophoric pyrene-perylene bisimide system investigated by De Cola and co-workers [16].

Perylene bisimide Poly(3-hexylthiophene) Solar cells Side chain crystallinity... 

Two of the classical bis-nitrogen ligands to assemble porphyrins (predominantly zinc metallated) are the bidentate l,4-diazabicyclo[2.2.2]octane (DABCO) and 4,4 -bipyridine (bipy). Other di-topic nitrogen-ligands studied include hydrazine, 4,4 -bipyrimidine, diaza-pyrene, 5,5 -dicyano-2,2 -bipyri-dine, perylene-bisimide, extended bipyridine units and non-covalently linked di-pyridyl ligands via bipy-metal interactions. The formation of various bis-porphyrin and multiporphyrin assemblies using these versatile ligands were studied in detail by Sanders, Anderson, Hunter, Branda and many others. The structures of the supramolecular multi-porphyrin architectures are schematically represented in Fig. 9. 

Fig.20 Schematic drawing of the bisporphyrin/perylene-bisimide assembly [ Ru(TPP) (CO) 2(m-PBI)] (16)...

Ultrafast spectroscopy experiments performed at the two excitation wavelengths afforded evidence that the side-to-face assembly 16 incorporating a perylene bisimide chromophore exhibits complex, interesting photophysics schematically summarized in Figs. 35 and 36. 

Sokkahngam, P., Lee C-H. (2011). Highly Sensitive Fluorescence "Turn-On" Indicator for Fluoride Anion with Remarkable Selectivity in Organic and Aqueous Media /. Org. Chem., 76,10, (May 2011), pp. 3820-3828, ISSN 10.1021/jo200138t Soh, N., Ueda, T. (2011). Perylene bisimide as a versatile fluorescent tool for environmental and biological analysis A review. Talanta, 85, 3, (Sept. 2011), pp. 1233-1237, ISSN 0039-9140... 

Much effort has been devoted to applying electron transfer in H-bonding system for the construction of optoelectronic devices and organic solar cells. For example, fullerene derivative and perylene bisimide have been assembled to form a El-bonded supramolecular system 28 through triple amino-carboxyhc acid interaction [86]. Under 63.2 mW/cm white light irradiation, the film made from the assembly on indium tin oxide (ITO) electrodes generated a steady and rapid photocurrent. The response of on/oflf cycling was prompt and reproducible. 

Recently, Braunschweig and co-workers reported the assembly of a three-component hydrogen bonding array 19-20-19 in toluene. The system is composed of two diketopyrrolopyrrole electron donors and one perylene bisimide (PDI) electron acceptor (Fig. 6.13) [56]. The hydrogen bonded three-component array stacked further into ID helical hierarchical stracture. Fluorescence and transient absorption spectroscopy showed that photoexcitation of the donor-acceptor superstmctures with visible light directed the system to achieve fast charge separation. 

Wurthner, F. Sautter, A. Highly fluorescent and electroactive molecular squares containing perylene bisimide ligands. Chem. Commun. 2000, (6). 445-446. 

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