TY - JOUR
T1 - Gold-Catalyzed Facile Synthesis and Crystal Structures of Benzene-/Naphthalene-Based Bispentalenes as Organic Semiconductors
AU - Sekine, Kohei
AU - Schulmeister, Jürgen
AU - Paulus, Fabian
AU - Goetz, Katelyn P.
AU - Rominger, Frank
AU - Rudolph, Matthias
AU - Zaumseil, Jana
AU - Hashmi, A. Stephen K.
N1 - Funding Information:
The authors are grateful to funding by the DFG (SFB 1249-N-Heteropolyzyklen als Funktionsmaterialien). We thank Michael Tçpper of Fraunhofer IZM, Berlin, Germany, for generously providing us with the BCB Cyclotene polymer.
Funding Information:
The authors are grateful to funding by the DFG (SFB 1249-N-Heteropolyzyklen als Funktionsmaterialien). We thank Michael T?pper of Fraunhofer IZM, Berlin, Germany, for generously providing us with the BCB Cyclotene polymer.
PY - 2019/1/2
Y1 - 2019/1/2
N2 - 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.
AB - 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.
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U2 - 10.1002/chem.201805637
DO - 10.1002/chem.201805637
M3 - Article
C2 - 30423210
AN - SCOPUS:85058838651
SN - 0947-6539
VL - 25
SP - 216
EP - 220
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 1
ER -