Chiral memory units based on dynamic redox systems with a dibenzoxepinone skeleton: Drastic change in racemization barrier and electrochemical bistability

Kazuhisa Wada; Yuna Chiba; Takashi Takeda; Hidetoshi Kawai; Ryo Katoono; Kenshu Fujiwara; Takanori Suzuki

doi:10.3987/COM-13-S(S)93

Chiral memory units based on dynamic redox systems with a dibenzoxepinone skeleton: Drastic change in racemization barrier and electrochemical bistability

Kazuhisa Wada, Yuna Chiba, Takashi Takeda, Hidetoshi Kawai, Ryo Katoono, Kenshu Fujiwara, Takanori Suzuki

Polymer Hybrid Materials Research Center

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

3 Citations (Scopus)

Abstract

The configuration of helical dicationic dyes 2²⁺ with a dihydrodibenzoxepinone unit is stable, whereas the corresponding neutral electron donors 1 with a tetrahydrophenanthroxepinone skeleton easily undergo ring-flip. Thanks to their electrochemical bistability, electron exchange between 1 and 2²⁺ is prohibited. Thus, the above electrochromic pairs 1/2²⁺ can serve as new members of less well-explored redox-based chiral-memory units.

Original language	English
Pages (from-to)	945-952
Number of pages	8
Journal	Heterocycles
Volume	88
Issue number	2
DOIs	https://doi.org/10.3987/COM-13-S(S)93
Publication status	Published - 2014

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

Access to Document

10.3987/COM-13-S(S)93

Fingerprint Dive into the research topics of 'Chiral memory units based on dynamic redox systems with a dibenzoxepinone skeleton: Drastic change in racemization barrier and electrochemical bistability'. Together they form a unique fingerprint.

Cite this

Chiral memory units based on dynamic redox systems with a dibenzoxepinone skeleton : Drastic change in racemization barrier and electrochemical bistability. / Wada, Kazuhisa; Chiba, Yuna; Takeda, Takashi; Kawai, Hidetoshi; Katoono, Ryo; Fujiwara, Kenshu; Suzuki, Takanori.

In: Heterocycles, Vol. 88, No. 2, 2014, p. 945-952.

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

@article{a10a40932dba409bb9d84c3115c49a35,

title = "Chiral memory units based on dynamic redox systems with a dibenzoxepinone skeleton: Drastic change in racemization barrier and electrochemical bistability",

abstract = "The configuration of helical dicationic dyes 22+ with a dihydrodibenzoxepinone unit is stable, whereas the corresponding neutral electron donors 1 with a tetrahydrophenanthroxepinone skeleton easily undergo ring-flip. Thanks to their electrochemical bistability, electron exchange between 1 and 22+ is prohibited. Thus, the above electrochromic pairs 1/22+ can serve as new members of less well-explored redox-based chiral-memory units.",

author = "Kazuhisa Wada and Yuna Chiba and Takashi Takeda and Hidetoshi Kawai and Ryo Katoono and Kenshu Fujiwara and Takanori Suzuki",

year = "2014",

doi = "10.3987/COM-13-S(S)93",

language = "English",

volume = "88",

pages = "945--952",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "2",

}

TY - JOUR

T1 - Chiral memory units based on dynamic redox systems with a dibenzoxepinone skeleton

T2 - Drastic change in racemization barrier and electrochemical bistability

AU - Wada, Kazuhisa

AU - Chiba, Yuna

AU - Takeda, Takashi

AU - Kawai, Hidetoshi

AU - Katoono, Ryo

AU - Fujiwara, Kenshu

AU - Suzuki, Takanori

PY - 2014

Y1 - 2014

N2 - The configuration of helical dicationic dyes 22+ with a dihydrodibenzoxepinone unit is stable, whereas the corresponding neutral electron donors 1 with a tetrahydrophenanthroxepinone skeleton easily undergo ring-flip. Thanks to their electrochemical bistability, electron exchange between 1 and 22+ is prohibited. Thus, the above electrochromic pairs 1/22+ can serve as new members of less well-explored redox-based chiral-memory units.

AB - The configuration of helical dicationic dyes 22+ with a dihydrodibenzoxepinone unit is stable, whereas the corresponding neutral electron donors 1 with a tetrahydrophenanthroxepinone skeleton easily undergo ring-flip. Thanks to their electrochemical bistability, electron exchange between 1 and 22+ is prohibited. Thus, the above electrochromic pairs 1/22+ can serve as new members of less well-explored redox-based chiral-memory units.

UR - http://www.scopus.com/inward/record.url?scp=84890925553&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84890925553&partnerID=8YFLogxK

U2 - 10.3987/COM-13-S(S)93

DO - 10.3987/COM-13-S(S)93

M3 - Article

AN - SCOPUS:84890925553

VL - 88

SP - 945

EP - 952

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 2

ER -