The photovoltaic parameters, i.e., the short‐circuit current, open‐circuit voltage and device fill factor, of bulk heterojunction solar cells that use perylene diimide (PDI) derivatives as electron acceptors are often far below the theoretically expected values for reasons still not entirely understood. This article demonstrates that the photovoltaic characteristics of blend films of regioregular poly(3‐hexylthiophene) (rr‐P3HT) and PDI molecules are improved upon using a core‐alkylated PDI derivative instead of the often used N‐alkylated PDI molecules. A doubling of the power conversion efficiency of P3HT:PDI solar cells by using the core‐alkylated PDI derivative is observed leading to an unprecedented power conversion efficiency of 0.5% for a P3HT:PDI solar cell under AM1.5 solar illumination. Furthermore, the optical properties of the novel PDI derivative are compared to two standard exclusively N‐alkylated PDI derivatives by steady‐state and time‐resolved photoluminescence spectroscopy in solution and solid state. The experiments reveal that aggregation in the solid state determines the photophysics of all PDI derivatives. However, the emission energy and excited state lifetime of the aggregates are clearly influenced by the alkyl‐substitution pattern through its effect on the packing of the PDI molecules. X‐ray diffraction experiments before and after thermal annealing of PDI:polystyrene and PDI:P3HT blends reveal subtle differences in the packing characteristics of the different PDI derivatives and, problematically, that P3HT ordering is suppressed by all of the PDI derivatives.
Describing wetting of a liquid on a rough or structured surface is a challenge because of the wide range of involved length scales. Nano- and micrometer-sized textures cause pinning of the contact line, reflected in a hysteresis of the contact angle. To investigate contact angles at different length scales, we imaged water drops on arrays of 5 μm high poly(dimethylsiloxane) micropillars. The drops were imaged by laser scanning confocal microscopy (LSCM), which allowed us to quantitatively analyze the local and large-scale drop profile simultaneously. Deviations of the shape of drops from a sphere decay at two different length scales. Close to the pillars, the amplitude of deviations decays exponentially within 1-2 μm. The drop profile approached a sphere at a length scale 1 order of magnitude larger than the pillars' height. The height and position dependence of the contact angles can be understood from the interplay of pinning of the contact line, the principal curvatures set by the topography of the substrate, and the minimization of the air-water interfaces.
Via an unprecedentedly reported ruthenium catalyzed reaction, an efficient and straightforward method was developed for the synthesis of 2,5,8,11-tetraboronate perylenediimide derivatives. A possible reaction mechanism is proposed. The synthesis of 2,5,8,11-tetra-iodo and tetra-amino perylenediimides derivatives is also reported.
Via one-step copper catalyzed procedures it was possible to synthesize 2,5,8,11-tetrabromo, tetrachloro, and tetracyano derivatives of perylenediimides. Characterization of optical and electrochemical properties of these materials proves substantial enhancement of the electron affinity, with a LUMO level as low as -4.4 eV in the case of the tetracyano perylenediimide.
Repeated precipitation of colloidal semiconductor quantum dots (QD) from a good solvent by adding a poor solvent leads to an increasing number of QD oligomers after redispersion in the good solvent. By using density gradient ultracentrifugation we have been able to separate QD monomer, dimer, and trimer fractions from higher oligomers in such solutions. In the corresponding fractions QD dimers and trimers have been enriched up to 90% and 64%, respectively. Besides directly coupled oligomers, QD dimers and trimers were also assembled by linkage with a rigid terrylene diimide dye (TDI) and separated again by ultracentrifugation. High-resolution transmission electron micrographs show that the interparticle distances are clearly larger than those for directly coupled dots proving that the QDs indeed are cross-linked by the dye. Moreover, energy transfer from the QDs to the TDI "bridge" has been observed. Individual oligomers (directly coupled or dye-linked) can be readily deposited on a substrate and studied simultaneously by scanning force and optical microscopy. Our simple and effective scheme is applicable to a wide range of ligand stabilized colloidal nanoparticles and opens the way to a detailed study of electronic coupling in, e.g., QD molecules.
Thin film field-effect transistors based on binary blends of poly(3-hexylthiophene) (P3HT) and two perylene diimide (PDI) derivatives with different alkyl substituents have been investigated in terms of device performance, microstructure and molecular organization on the surface. For the same blend ratios the PDIs phase separate differently due to solubility variation. Blends with a horizontal phase separation between the donor and acceptor show ambipolar behavior due to well defined homogenous pathways for both charge carriers. In this layer arrangement the polymer is located near the dielectric interface, while the PDI molecules crystallize on top of the film. Interestingly, the electron mobility is improved by a few orders of magnitude in comparison to the pure acceptor. This increase is attributed to the altered microstructure of PDI in the blends. Layers in which the PDI crystals are embedded within the polymer matrix and are not interconnected with each other lead only to hole transport in the transistor. For one blend ratio, the hole mobility improves by one order of magnitude compared to pure P3HT as a result of the reorganization of the polymer in the blend layer. This study provides new insights into the role of microstructure and molecular organization in the charge carrier transport in heterojunction field-effect transistors for the development of high-performance future devices.
Polypeptides are successfully incorporated into poly(l-lactide) (PLLA) chains in a ring-opening polymerization (ROP) of l-lactide by using them as initiators. The resulting ABA triblock copolymers possess molecular weights up to 11000 g·mol(-1) and polydispersities as low as 1.13, indicating the living character of the polymerization process. In a nonaqueous emulsion, peptide-initiated polymerization of l-lactide leads to well-defined nanoparticles, consisting of PLLA-block-peptide-block-PLLA copolymer. These nanoparticles are easily loaded by dye-encapsulation and transferred into aqueous media without aggregation (average diameter of 100 nm) or significant dye leakage. Finally, internalization of PLLA-block-peptide-block-PLLA nanoparticles by HeLa cells is demonstrated by a combination of coherent anti-Stokes Raman spectroscopy (CARS) and fluorescence microscopy. This demonstrates the promise of their utilization as cargo delivery vehicles.
We present relevant results dealing with the transparency/optical nonlinearity trade-off in high-frequency electro-optic applications. The very simple, stable and high optical gap chromophore, the zwitterion 1-methyl-4-(tetrazol-5-ate)pyridinium, represents the best transparency/optical nonlinearity trade-off so far described in the literature. We rationalize this remarkable performance in the framework of the Bond Length Alternation theory by means of a multidisciplinary approach including: single crystal X-ray structure, Electric Field Induced Second-Harmonic Generation, solvatochromism, electrochemistry and thermal analyses.
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