Synthesis, physical properties, and chemistry of donor–acceptor-substituted pentacenes

Author:

Lehnherr Dan1,Adam Matthias2,Murray Adrian H.1,McDonald Robert3,Hampel Frank2,Tykwinski Rik R.12

Affiliation:

1. Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada.

2. Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität, Erlangen-Nürnberg, Henkestr. 42, 91054 Erlangen, Germany.

3. X-ray Crystallography Lab, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada.

Abstract

Pentacenes bearing electron-donating and (or) -withdrawing groups, namely methoxy-, dialkylamino-, and nitroaryl moieties, are synthesized to afford polarized pentacenes. The optical, electrochemical, and chemical properties of these derivatives are explored. The cycloaddition reaction of selected derivatives with tetracyanoethylene (TCNE) is explored, and the experimental results are rationalized on the basis calculations using density functional theory (DFT). X-ray crystallographic data provides insight into the molecular structure and intermolecular interactions present in the solid state.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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