A helically-twisted ladder based on 9,90-bifluorenylidene: Synthesis, characterization, and carrier-transport properties

Jinjia Xu; Atsuro Takai; Alisa Bannaron; Takafumi Nakagawa; Yutaka Matsuo; Manabu Sugimoto; Masayuki Takeuchi; Masayuki Takeuchi

doi:10.1039/c7qm00583k

A helically-twisted ladder based on 9,90-bifluorenylidene: Synthesis, characterization, and carrier-transport properties

Jinjia Xu, Atsuro Takai, Alisa Bannaron, Takafumi Nakagawa, Yutaka Matsuo, Manabu Sugimoto, Masayuki Takeuchi, Masayuki Takeuchi

University of Missouri-St. Louis

Research output: Contribution to journal › Article › peer-review

Abstract

We synthesized a ladder-shaped 9,9 0 -bifluorenylidene cyclic dimer (CBF), in which the two 9,9 0 -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 9,9 0 -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.

Original language	American English
Journal	Materials Chemistry Frontiers
Volume	2
DOIs	https://doi.org/10.1039/c7qm00583k
State	Published - 2018

Disciplines

Biochemistry, Biophysics, and Structural Biology

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title = "A helically-twisted ladder based on 9,90-bifluorenylidene: Synthesis, characterization, and carrier-transport properties",

abstract = " We synthesized a ladder-shaped 9,9 0 -bifluorenylidene cyclic dimer (CBF), in which the two 9,9 0 -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 9,9 0 -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. ",

author = "Jinjia Xu and Atsuro Takai and Alisa Bannaron and Takafumi Nakagawa and Yutaka Matsuo and Manabu Sugimoto and Masayuki Takeuchi and Masayuki Takeuchi",

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doi = "10.1039/c7qm00583k",

language = "American English",

volume = "2",

journal = "Materials Chemistry Frontiers",

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T1 - A helically-twisted ladder based on 9,90-bifluorenylidene: 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 - Takeuchi, Masayuki

PY - 2018

Y1 - 2018

N2 - We synthesized a ladder-shaped 9,9 0 -bifluorenylidene cyclic dimer (CBF), in which the two 9,9 0 -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 9,9 0 -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 9,9 0 -bifluorenylidene cyclic dimer (CBF), in which the two 9,9 0 -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 9,9 0 -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.

UR - https://doi.org/10.1039/c7qm00583k

U2 - 10.1039/c7qm00583k

DO - 10.1039/c7qm00583k

M3 - Article

VL - 2

JO - Materials Chemistry Frontiers

JF - Materials Chemistry Frontiers

ER -

A helically-twisted ladder based on 9,90-bifluorenylidene: Synthesis, characterization, and carrier-transport properties

Abstract

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