Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Since azaacenes have electron-deficient backbones and lone-pair electrons on nitrogen centers, they can efficiently detect the target molecules or ions through supramolecular interactions such as anion–π attractions and coordinate bonding. These special features make azaacenes very designable for various sensors, which can be further used in the bio field. In this review, we will summarize the recent progress in the applications of azaacenes in sensing and bio fields. We believe that a rapid development in the research of sensors and bio applications based on azaacenes will be witnessed in the coming years due to their tuneable structures, optical properties and binding abilities.

Azaacenes as active elements for sensing and bio applications

Our research progress in heteroaggregation and homoaggregation of organic π-conjugated systems

Four novel unsymmetrical heteroacenes containing five-membered heterocycles (OPyN, TPyN, TPyC, TPyO) have been synthesized and characterized. The formed molecules exhibited twisted structures, determined by crystal analysis and showed blue/green fluorescence in dichloromethane and in thin film. Compounds OPyN and TPyN were selectively used as active ingredients, and the fabricated devices displayed promising electroluminescent performance.

Synthesis, Crystal Analyses, Physical Properties, and Electroluminescent Behavior of Unsymmetrical Heterotwistacenes.

Over the last two decades fluorescent materials have strongly influenced the technological development of modern societies. Ranging from organic photovoltaic to OLED TVs, from highly sensitive early detection methods of diseases to the sensing of environmental pollutants, a multitude of applications have been developed exploiting the beneficial properties of such materials. Future technologies based on fluorescent molecules may act as leverage for transforming our society into a place of a sustainable economy, at the same time raising our standard of living. Modern heterocyclic molecules are at the core of this development of fluorescence. This chapter gives an overview on recent developments and trends in the field of fluorescent heterocyclic molecules of selected systems. Starting with their synthesis, modern applications and studies of these molecules are discussed and integrated into the larger context of technological developments.

Fluorescent heterocycles: Recent trends and new developments

A series of pyrene/phenanthrene-fused furan derivatives (1-8) were synthesized by a simple condensation reaction between pyrene-4,5-diketone/phenanthrenequinone and substituted phenol/naphthol in the presence of trifluoromethanesulfonic acid in 1,2-dichlorobenzene heated at reflux. The formed compounds can emit strong blue light in organic solvents. Additionally, the self-assembly behaviors of two of the compounds (3 and 5) were studied through re-precipitation method and the resulting nanostructures were characterized by UV/Vis, fluorescence spectra, and field-emission scanning electron microscopy (FESEM). The findings showed that the shape and size of compounds 3 and 5 could be tuned by the ratio of THF and hexadecyl trimethyl ammonium bromide (CTAB) solution in water.

Synthesis, Photophysics, and Self-Assembly of Furan-Embedded Heteroarenes.

https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/chem.201584204

Back Cover: Synthesis, Photophysics, and Self‐Assembly of Furan‐Embedded Heteroarenes (Chem. Eur. J. 42/2015)

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Synthesis, Photophysics, and Self-Assembly of Furan-Embedded Heteroarenes.

Back Cover: Synthesis, Photophysics, and Self‐Assembly of Furan‐Embedded Heteroarenes (Chem. Eur. J. 42/2015)