An efficient synthesis of 2,6-disubstituted benzobisoxazoles: new building blocks for organic semiconductors.
TL;DR: 2,6-Disubstituted benzobisoxazoles have been synthesized by a highly efficient reaction of diaminobenzene diols with various orthoesters and the utility of these compounds as building blocks for the synthesis of conjugated polymers is demonstrated.
About: This article is published in Organic Letters.The article was published on 2008-10-03. It has received 51 citations till now.
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TL;DR: In this article, a review of π-conjugated polymeric semiconductors for organic thin-film (or field effect) transistors (OTFTs or OFETs) and bulk-heterojunction photovoltaic (or solar) cell (BHJ-OPV or OSC) applications are summarized and analyzed.
Abstract: The optoelectronic properties of polymeric semiconductor materials can be utilized for the fabrication of organic electronic and photonic devices. When key structural requirements are met, these materials exhibit unique properties such as solution processability, large charge transporting capabilities, and/or broad optical absorption. In this review recent developments in the area of π-conjugated polymeric semiconductors for organic thin-film (or field-effect) transistors (OTFTs or OFETs) and bulk-heterojunction photovoltaic (or solar) cell (BHJ-OPV or OSC) applications are summarized and analyzed.
2,076 citations
Patent•
11 Apr 2007
TL;DR: Tandem photovoltaic cells, as well as related components, systems, and methods, are disclosed in this paper, where the authors also present a comparison of the two types of cells.
Abstract: Tandem photovoltaic cells, as well as related components, systems, and methods, are disclosed.
120 citations
TL;DR: By combining substituted anilines with functionalized orthoesters, an efficient and connective methodology for the preparation of benzoxazole, benzothiazole, and benzimidazole derivatives has been established and enables the development of new libraries of heterocycles containing multifunctional sites.
90 citations
TL;DR: The group's work on benzobisoxazole molecular cruciforms is summarized, which includes studies to benzimidazole-based "half-cruciforms", which are L-shaped rigid fluorophores that maintain most of the spatial separation of FMOs observed in benzob isoxazol cruciformS.
Abstract: ConspectusCross-conjugated molecular cruciforms are intriguing platforms for optoelectronic applications. Their two intersecting π-conjugated arms allow independent modulation of the molecules’ HOMO and LUMO levels and guarantee a well-defined optical response to analyte binding. In addition, the rigid cross-conjugated geometries of these molecules allow their organization in two- and three-dimensional space with long-range order, making them convenient precursors for the transition from solution-based to the more practical solid-state- and surface-based devices. Not surprisingly, a number of molecular cruciform classes have been explored because of these appealing properties. These include tetrakis(arylethynyl)benzenes, tetrastyrylbenzenes, distyrylbis(arylethynyl)benzenes, tetraalkynylethenes, biphenyl-based “swivel” cruciforms, and benzobisoxazole-based cruciforms.In this Account, we summarize our group’s work on benzobisoxazole molecular cruciforms. The heterocyclic central core of these molecules for...
62 citations
References
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TL;DR: In this article, a double-layer structure of organic thin films was prepared by vapor deposition, and efficient injection of holes and electrons was provided from an indium-tinoxide anode and an alloyed Mg:Ag cathode.
Abstract: A novel electroluminescent device is constructed using organic materials as the emitting elements. The diode has a double‐layer structure of organic thin films, prepared by vapor deposition. Efficient injection of holes and electrons is provided from an indium‐tin‐oxide anode and an alloyed Mg:Ag cathode. Electron‐hole recombination and green electroluminescent emission are confined near the organic interface region. High external quantum efficiency (1% photon/electron), luminous efficiency (1.5 lm/W), and brightness (>1000 cd/m2) are achievable at a driving voltage below 10 V.
13,185 citations
TL;DR: Research in the use of organic polymers as active semiconductors in light-emitting diodes has advanced rapidly, and prototype devices now meet realistic specifications for applications.
Abstract: Research in the use of organic polymers as the active semiconductors in light-emitting diodes has advanced rapidly, and prototype devices now meet realistic specifications for applications. These achievements have provided insight into many aspects of the background science, from design and synthesis of materials, through materials fabrication issues, to the semiconductor physics of these polymers.
5,653 citations
TL;DR: In this article, the authors presented a review of several organic photovoltaics (OPV) technologies, including conjugated polymers with high-electron-affinity molecules like C60 (as in the bulk-heterojunction solar cell).
Abstract: There has been an intensive search for cost-effective photovoltaics since the development of the first solar cells in the 1950s. [1–3] Among all alternative technologies to silicon-based pn-junction solar cells, organic solar cells could lead the most significant cost reduction. [4] The field of organic photovoltaics (OPVs) comprises organic/inorganic nanostructures like dyesensitized solar cells, multilayers of small organic molecules, and phase-separated mixtures of organic materials (the bulkheterojunction solar cell). A review of several OPV technologies has been presented recently. [5] Light absorption in organic solar cells leads to the generation of excited, bound electron– hole pairs (often called excitons). To achieve substantial energy-conversion efficiencies, these excited electron–hole pairs need to be dissociated into free charge carriers with a high yield. Excitons can be dissociated at interfaces of materials with different electron affinities or by electric fields, or the dissociation can be trap or impurity assisted. Blending conjugated polymers with high-electron-affinity molecules like C60 (as in the bulk-heterojunction solar cell) has proven to be an efficient way for rapid exciton dissociation. Conjugated polymer–C60 interpenetrating networks exhibit ultrafast charge transfer (∼40 fs). [6,7] As there is no competing decay process of the optically excited electron–hole pair located on the polymer in this time regime, an optimized mixture with C60 converts absorbed photons to electrons with an efficiency close to 100%. [8] The associated bicontinuous interpenetrating network enables efficient collection of the separated charges at the electrodes. The bulk-heterojunction solar cell has attracted a lot of attention because of its potential to be a true low-cost photovoltaic technology. A simple coating or printing process would enable roll-to-roll manufacturing of flexible, low-weight PV modules, which should permit cost-efficient production and the development of products for new markets, e.g., in the field of portable electronics. One major obstacle for the commercialization of bulk-heterojunction solar cells is the relatively small device efficiencies that have been demonstrated up to now. [5] The best energy-conversion efficiencies published for small-area devices approach 5%. [9–11] A detailed analysis of state-of-the-art bulk-heterojunction solar cells [8] reveals that the efficiency is limited by the low opencircuit voltage (Voc) delivered by these devices under illumination. Typically, organic semiconductors with a bandgap of about 2 eV are applied as photoactive materials, but the observed open-circuit voltages are only in the range of 0.5–1 V. There has long been a controversy about the origin of the Voc in conjugated polymer–fullerene solar cells. Following the classical thin-film solar-cell concept, the metal–insulator–metal (MIM) model was applied to bulk-heterojunction devices. In the MIM picture, Voc is simply equal to the work-function difference of the two metal electrodes. The model had to be modified after the observation of the strong influence of the reduction potential of the fullerene on the open-circuit volt
4,816 citations
IBM1
TL;DR: In this article, the authors present new insight into conduction mechanisms and performance characteristics, as well as opportunities for modeling properties of organic thin-film transistors (OTFTs) and discuss progress in the growing field of n-type OTFTs.
Abstract: Organic thin-film transistors (OTFTs) have lived to see great improvements in recent years. This review presents new insight into conduction mechanisms and performance characteristics, as well as opportunities for modeling properties of OTFTs. The shifted focus in research from novel chemical structures to fabrication technologies that optimize morphology and structural order is underscored by chapters on vacuum-deposited and solution-processed organic semiconducting films. Finally, progress in the growing field of the n-type OTFTs is discussed in ample detail. The Figure, showing a pentacene film edge on SiO2, illustrates the morphology issue.
4,804 citations
TL;DR: Polymer-based organic photovoltaic systems hold the promise for a cost-effective, lightweight solar energy conversion platform, which could benefit from simple solution processing of the active layer.
Abstract: Fossil fuel alternatives, such as solar energy, are moving to the forefront in a variety of research fields. Polymer-based organic photovoltaic systems hold the promise for a cost-effective, lightweight solar energy conversion platform, which could benefit from simple solution processing of the active layer. The function of such excitonic solar cells is based on photoinduced electron transfer from a donor to an acceptor. Fullerenes have become the ubiquitous acceptors because of their high electron affinity and ability to transport charge effectively. The most effective solar cells have been made from bicontinuous polymer–fullerene composites, or so-called bulk heterojunctions. The best solar cells currently achieve an efficiency of about 5 %, thus significant advances in the fundamental understanding of the complex interplay between the active layer morphology and electronic properties are required if this technology is to find viable application.
3,911 citations