TY - JOUR
T1 - A helically-twisted ladder based on 9,90-bifluorenylidene
T2 - Synthesis, characterization, and carrier-transport properties
AU - Xu, Jinjia
AU - Takai, Atsuro
AU - Bannaron, Alisa
AU - Nakagawa, Takafumi
AU - Matsuo, Yutaka
AU - Sugimoto, Manabu
AU - Matsushita, Yoshitaka
AU - Takeuchi, Masayuki
N1 - Funding Information:
We are grateful to Dr Takeshi Yasuda (NIMS) for fruitful discussion, DAICEL Corporation for the trial on chiral HPLC experiments. Mr Toshikane Suzuki (NIMS) is greatly acknowledged for his contribution in the initial stages of this work. This research was supported by Grants-in-Aid for Scientific Research on Innovative Areas ‘‘p-System Figuration’’ from JSPS (26102009 for M. T. and 26102015 for M. S.) and on Challenging Research (Exploratory, JP17K19116 for Y. M.), the Green Asia program (Kyushu University) for A. B., the MEXT ‘‘NIMS Molecule and Material Synthesis Platform’’ program, and the Materials Analysis Station of NIMS.
Funding Information:
We are grateful to Dr Takeshi Yasuda (NIMS) for fruitful discussion, DAICEL Corporation for the trial on chiral HPLC experiments. Mr Toshikane Suzuki (NIMS) is greatly acknowledged for his contribution in the initial stages of this work. This research was supported by Grants-in-Aid for Scientific Research on Innovative Areas ''p-System Figuration'' from JSPS (26102009 for M. T. and 26102015 for M. S.) and on Challenging Research (Exploratory, JP17K19116 for Y. M.), the Green Asia program (Kyushu University) for A. B., the MEXT ''NIMS Molecule and Material Synthesis Platform'' program, and the Materials Analysis Station of NIMS.
Publisher Copyright:
© The Royal Society of Chemistry and the Chinese Chemical Society 2018
PY - 2018
Y1 - 2018
N2 - We synthesized a ladder-shaped 9,90-bifluorenylidene cyclic dimer (CBF), in which the two 9,90-bifluorenylidene units are connected directly with two covalent bonds. CBF has a pair of enantiomers which are alternately packed in a perpendicular fashion in the crystal, and these enantiomers exhibit rapid interconversion in solution. Owing to the ladder-type connection, the two 9,90-bifluorenylidene units in CBF electronically interact upon redox, and thus the structure of CBF is changed stepwise during the oxidation and reduction processes, which was confirmed by electrochemistry and quantum chemical calculations. The p-network of CBF in the solid state leads to its hole transport properties.
AB - We synthesized a ladder-shaped 9,90-bifluorenylidene cyclic dimer (CBF), in which the two 9,90-bifluorenylidene units are connected directly with two covalent bonds. CBF has a pair of enantiomers which are alternately packed in a perpendicular fashion in the crystal, and these enantiomers exhibit rapid interconversion in solution. Owing to the ladder-type connection, the two 9,90-bifluorenylidene units in CBF electronically interact upon redox, and thus the structure of CBF is changed stepwise during the oxidation and reduction processes, which was confirmed by electrochemistry and quantum chemical calculations. The p-network of CBF in the solid state leads to its hole transport properties.
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U2 - 10.1039/c7qm00583k
DO - 10.1039/c7qm00583k
M3 - Article
AN - SCOPUS:85059947538
SN - 2052-1537
VL - 2
SP - 780
EP - 784
JO - Materials Chemistry Frontiers
JF - Materials Chemistry Frontiers
IS - 4
ER -