5 years ago

Rodlike Tetracene Derivatives

Rodlike Tetracene Derivatives
Michael Roth, Marcus Ahles, Roland Schmechel, Christian Gawrisch, Christian Melzer, Matthias Rehahn, Heinz von Seggern, Thorsten Schwalm
Efficient and versatile synthetic access to rodlike tetracene derivatives was developed by means of Diels–Alder cycloaddition, halogenation, halogen–metal exchange, and transition metal mediated coupling reactions. Herein, the synthesis and structural, electrical, and charge-transport properties of three of the resulting materials, namely, 2-(tetracen-2-yl)tetracene, 1,4-bis(2-tetracenyl)benzene, and 2,5-bis(2-tetracenyl)thiophene, are presented. Good crystallization behavior on SiO2 substrates, narrowing of the bandgap by 0.2 eV, and a decrease of the ionization potential of more than 0.5 eV compared to tetracene were observed. Charge-carrier field-effect mobilities on the order of 10−1 cm2 V−1 s−1, on/off ratios of 105, and threshold voltages Vth<15 V were found in thin-film organic field-effect transistors prepared by standard high-vacuum deposition techniques. Different aspects: By merging two tetracenes, new ridged-rod tetracene derivatives with different aspect ratios were realized. Coupling of the two tetracenes reduces the bandgap and ionization potential. Good crystallinity on SiO2 substrates was observed. Thus, decent performance in organic field-effect transistors was found (see figure), but increasing the aspect ratio beyond that of directly linked tetracenes did not result in improved crystallinity or transport properties. DDQ: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, DT: ditetracene, SYC: Semmelhack–Yamamoto coupling.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702382

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.