Gold‐Catalyzed Facile Synthesis and Crystal Structures of Benzene‐/Naphthalene‐Based Bispentalenes as Organic Semiconductors. Issue 1 (17th December 2018)

• Record Type: Journal Article
• Authors: Sekine, Kohei; Schulmeister, Jürgen; Paulus, Fabian; Goetz, Katelyn P.; Rominger, Frank; Rudolph, Matthias; Zaumseil, Jana; Hashmi, A. Stephen K.
• Is Part Of: Chemistry. Volume 25:Issue 1(2019)
• Page Start: 216
• Page End: 220
• Publication Date: 2018-12-17
• Subjects: gold catalysis -- organic-field-effect transistor -- pentalene -- polycyclic aromatic hydrocarbons -- tetrayne; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201805637
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The gold‐catalyzed facile synthesis of U‐shaped and S‐shaped bispentalenes is described from easily available tetra(arylethynyl)‐benzenes and ‐naphthalenes. The optoelectronic and transistor properties were also investigated. The selectivity between the U‐shaped and S‐shaped bispentalene isomers can be tuned by the bulkiness of the ligand and the substrates. The S‐shaped naphthalene‐based bispentalene shows a one‐dimensional face‐to‐face packing pattern in solid state and a good hole mobility, indicating that the S‐shaped bispentalene core is highly suitable for transistor applications. The gold‐catalyzed annulation of tetraynes provides a useful protocol in the synthesis of bispentalenes for organic semiconductors. Abstract : The gold‐catalyzed annulation of tetraynes provides a useful protocol in the synthesis of U‐shaped and S‐shaped bispentalenes for organic semiconductors. The naphthalene‐based S‐shaped naphthalene‐based bispentalene shows a one dimensional face‐to‐face packing pattern in solid state and a good hole mobility.