2021
DOI: 10.1021/jacs.1c00189
View full text | Cite
|
Sign up to set email alerts
|

Abstract: Octaaryl-substituted bisquinodimethanes (BQDs) with a zigzag structure were designed as redox switchable molecules that undergo four-electron oxidation to produce tetracationic pentacenes with a doubly twisted structure. In contrast to one-stage four-electron oxidation of BQDs, stepwise two-electron reduction of tetracationic pentacenes occurs to give dicationic anthracenes and then the original BQDs, step-by-step. Since both tetra-/dications exhibit near-infrared (NIR) absorptions (-1,400 nm) based on an intr… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
2
1

Citation Types

1
19
0

Year Published

2021
2021
2022
2022

Publication Types

Select...
4

Relationship

1
3

Authors

Journals

citations
Cited by 16 publications
(20 citation statements)
references
References 54 publications
(85 reference statements)
1
19
0
Order By: Relevance
“…On the other hand, the authors found that bisquinodimethane (BQD, m = 2) derivative 7 exhibits a large change in its structure upon redox interconversion, which is referred to as a dyrex system, [91][92][93] and also shows hysteretic behavior, where the oxidation of 7 and reduction of 7 4 + take different paths. [94] BQDs were designed and synthesized as accumulated analogues of anthraquinodimethanes (AQDs, m = 1), which have been previously reported to be a dyrex system by the authors (Scheme 3). [95,96] Notably, the cyclic voltammogram of BQD 7 showed that oxidation proceeds via a one-stage four-electron process [E ox = + 1.26 V vs. SCE (+ 0.73 V vs. Fc/Fc + )] to produce tetracation 7 À ) 2 was isolated quantitatively.…”
Section: Pure Hydrocarbon-based Dynamic Redox (Dyrex) Systemmentioning
confidence: 99%
“…On the other hand, the authors found that bisquinodimethane (BQD, m = 2) derivative 7 exhibits a large change in its structure upon redox interconversion, which is referred to as a dyrex system, [91][92][93] and also shows hysteretic behavior, where the oxidation of 7 and reduction of 7 4 + take different paths. [94] BQDs were designed and synthesized as accumulated analogues of anthraquinodimethanes (AQDs, m = 1), which have been previously reported to be a dyrex system by the authors (Scheme 3). [95,96] Notably, the cyclic voltammogram of BQD 7 showed that oxidation proceeds via a one-stage four-electron process [E ox = + 1.26 V vs. SCE (+ 0.73 V vs. Fc/Fc + )] to produce tetracation 7 À ) 2 was isolated quantitatively.…”
Section: Pure Hydrocarbon-based Dynamic Redox (Dyrex) Systemmentioning
confidence: 99%
“…Studies by Ishigaki and Suzuki et al. describe the fabrication of various functional C x H y molecules that exhibit interesting redox behaviors, even though electrochromic devices have not been reported [108–110] . For example, they used two spiro(dibenzocycloheptatriene) units to synthesize 9,10‐dihydrophenanthrene and observed a color change (from colorless to red) associated with C−C bond cleavage after two‐electron oxidation [110] .…”
Section: Cxhy Molecules In Organic Electronic Devicesmentioning
confidence: 99%
“…Recently, they reported an octaaryl‐substituted bisquinodimethane with a zigzag structure. This C x H y molecule underwent four‐electron oxidation at the positive scan and two‐step four‐electron reduction at the following negative scan, wherein two electrons were involved in each cathodic process and the oxidative step was associated with a vivid color change [108] . Furthermore, in the Supporting Information, Section III‐2, monoelectrochromic devices using C 60 are discussed.…”
Section: Cxhy Molecules In Organic Electronic Devicesmentioning
confidence: 99%
“…Recently, Suzuki demonstrated that by adjusting the energy gap between the folded and twisted configurations with thienyl groups, both redox and magnetic properties could be controlled thermally . These examples, among others, elegantly manifested how tailored molecular design could fine-tune the delicate energy balance between the electronic factor, featured by aromaticity and π-bond breaking, and the steric factor, featured by structural change. For a rational design of such multifunctional materials, a deeper understanding on the structure–electronic states–property relationship is highly desirable.…”
Section: Introductionmentioning
confidence: 99%