FUNCTIONAL CHROMOPHORES FOR LIGHT-HARVESTING APPLICATIONS

This doctoral thesis describes the design, synthesis and characterization as well as investigations of the optical properties of new functional chromophores. In the recent years, the term “functional dyes” used in a wild range of application areas, such as dyes for liquid crystals, lasers, displays, solar cells or bioimaging emphasize on the new functionality beyond color of π-conjugated chromophores.[1] In Chapter I a briefly insight into the general aspects of functional chromophores and emitters for light-harvesting, along with a concise outline of the manuscript is given to the reader. The preparation and physical characterization of oligo(p-phenylene vinylene)-derived single-walled carbon nanotubes (SWCNTs) conjugates are described in Chapter II. Moreover, further testing of functionalized SWCNTs as doping agents for spiro-OMeTAD in a flat CH3NH3PbI3-based solar cell was presented. Chapter III describes the synthesis of a novel class of O-doped polyaromatic hydrocarbons, in which two polyaromatic hydrocarbon substructures are bridged through one or two O atoms. This includes high-yielding ring-closure key steps that, depending on the reaction conditions, allow the formation of either furanyl or pyranyl structure through intramolecular C-O bond formation, and the stepwise planarization of oligonaphthalenes. X-ray single-crystal diffraction showed that the furanyl derivatives undergo π-π stacking at the solid state. Photophysical measurements showed very nicely that the molecules feature high emission yield and tunable absorption UV-Vis properties. Finally, Chapter IV reports the preparation of a distinct category of π-conjugates, more in detail; a new family of bis-perylenol derivatives bearing different dihedral angles between the two perylene moieties was prepared and studied in terms of UV-Vis and emission spectroscopy. [1] a) Chen, Z.; Lohr, A.; Saha-Möller, C. R.; Würthner, F. Chem. Soc. Rev.2009, 38, 564–584. b) Weil, T.; Vosch, T.; Hofkens, J.; Peneva, K.; Müllen, K. Angew. Chemie - Int. Ed.2010, 49, 9068–9093