Synthesis and Characterization of Soluble Directly 2, 2′‐Linked Tetracene Dimer. Issue 11 (28th November 2018)

• Record Type: Journal Article
• Authors: Honda, Tasuku; Nagahara, Masaya; Taka, Naohiro; Nishida, Jun‐ichi; Kawase, Takeshi; Ono, Katsuhiko; Kobayashi, Takashi; Naito, Hiroyoshi; Kitamura, Chitoshi
• Is Part Of: European journal of organic chemistry. Issue 11(2019)
• Page Start: 2107
• Page End: 2114
• Publication Date: 2018-11-28
• Subjects: Semiconductors -- Polycyles -- Dimerization -- UV/Vis spectroscopy -- X‐ray diffraction; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801333
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A soluble directly 2, 2′‐linked tetracene dimer was synthesized. Dimerization of 8‐bromo‐2, 3‐dihexyl‐5, 12‐tetracenequinone afforded the corresponding bitetracenequinone, which was converted into a tetracene dimer by sequential addition of 1‐hexynyllithium and SnCl2 /HCl. The synthesized tetracene dimer with four hexyl and four 1‐hexynyl groups was highly soluble in CH2 Cl2 and THF, and the solutions were unstable under air and room light. The compound was studied by X‐ray single crystal analysis, UV/Vis, and fluorescence spectroscopy, cyclic voltammetry, and density functional theory (DFT) calculations. In the crystal, two tetracene rings take a coplanar conformation although DFT calculations demonstrated that such a molecular structure is energetically unfavorable. The tetracene dimer had red‐shifted absorption maxima and large molar extinction coefficients compared with the corresponding tetracene monomer. The tetracene dimer also showed amphoteric redox properties and p ‐type semiconducting behavior. Abstract : A soluble directly 2, 2′‐linked tetracene dimer was prepared, and its properties were characterized by crystal structure analysis, UV/Vis and fluorescence spectroscopy, cyclic voltammetry, DFT calculations, and OFET measurements.