Two-way chromic interconversion of the 2,2′-biphenol-6,6′-diyl dication with 5H,10H-dioxapyrene or 9H,10H-4,5-dihydroxyphenanthrene

Sakano, Yuto; Katoono, Ryo; Fujiwara, Kenshu; Suzuki, Takanori

doi:10.1039/c5cc06338h

Cited by 6 publications

(3 citation statements)

References 26 publications

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“…Suzuki and his group have also used a dihydroxy-1,1'biphenyl scaffold to preorganize two acridinium units (13 2 + , Scheme 6a). [25] As expected, this system exhibits an electrochemical hysteresis loop (E Ox = + 0.32 V and E Red = À 0.23 V vs SCE) in a CH 2 Cl 2 /CH 3 CN (4 : 1) solvent mixture. However, the bisacridinium form is also chemically responsive to the addition of Scheme 4.…”

Section: Multi-input and Multi-output Responsive Systemssupporting

confidence: 74%

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N‐Substituted Acridinium as a Multi‐Responsive Recognition Unit in Supramolecular Chemistry

Rouville

Heitz

2021

ChemPlusChem

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The N-substituted acridinium motif is an electron-deficient unit with appealing multi-responsive properties which have been exploited in the field of supramolecular chemistry. This building block reversibly alters its shape, with its chemical and optical properties in response to a chemical or redox signal. In this Review, we discuss selected examples where the switchable properties of 9-aryl-N-methyl-acridinium lead to actuators, multi-input and multi-output systems, host or guest systems, and to interlocked systems with controllable motion.

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Section: Multi-input and Multi-output Responsive Systemssupporting

confidence: 74%

“…[24] Scheme 6. Responsive acridinium systems upon chemical and electrochemical stimuli a) from T. Suzuki and co-workers (13 2 + ) [25] and b) from T. Kubo and co-workers (15 + ). [26] Reproduced from reference [26] with permission from Wiley-VCH.…”

Section: Multi-input and Multi-output Responsive Systemsmentioning

confidence: 99%

N‐Substituted Acridinium as a Multi‐Responsive Recognition Unit in Supramolecular Chemistry

Rouville

Heitz

2021

ChemPlusChem

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“…This is because their combination can bring electron and proton transfer activities. For example, intramolecular acridi-nium-phenoxide zwitterions served as a single-electron-transfer catalyst [6] and a two-way interconversion system [7] are promising materials. In addition, a homolytic bond cleavage was observed in the photo-induced ring-opening reaction of acridiniumalkoxide spiropyrans.…”

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confidence: 99%

Redox/pH Dual Stimuli‐Responsive Acridine Spiropyran

et al. 2019

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A spiropyran derivative containing an acridinium and a phenoxide moieties was found to exhibit both halochromism and electrochromism in response to acid stimulation and oxidative stimulation, respectively. Variable scan-rate voltammetric studies revealed that the acridine spiropyran undergoes a reversible conversion between a closed-ring and an open-ring form during the redox cycle. The presence of a ring-opened radical cation species was demonstrated by simultaneous electrochemical ESR measurements.

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Conformational Switching through the One‐Electron Reduction of an Acridinium‐based, γ‐Cationic Phosphine Gold Complex

Liu

Kim

Gabbaı̈

2021

Chemistry A European J

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Our efforts in the chemistry of gold complexes featuring ambiphilic phosphine‐carbenium L/Z‐type ligand have led us to consider the reduction of the carbenium moiety as a means to modulate the gold–carbenium interaction present in these complexes. Here, it was shown that the one‐electron reduction of [(o‐Ph2P(C6H4)Acr)AuCl]+ (Acr=9‐N‐methylacridinium) produces a neutral stable radical, the structure of which showed a marked increase in the Au–Acr distance. Related structural changes were observed for the phosphine oxide analogue [(o‐Ph2P(O)(C6H4)Acr]+, the reduction of which interfered with the P=O→carbenium interaction. These structural effects, driven by a reduction‐induced change in the electronic and electrostatic characteristics of the compounds, showed that the charge and accepting properties of the carbenium unit can be modulated. These results highlight the redox‐noninnocence of carbenium Z‐type ligand, a feature that can be exploited to induce specific conformational changes.

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Two-way chromic interconversion of the 2,2′-biphenol-6,6′-diyl dication with 5H,10H-dioxapyrene or 9H,10H-4,5-dihydroxyphenanthrene

Abstract: Two-proton or two-electron transfer of the title biphenolic dication proceeds nearly simultaneously to induce 2,6'/2',6- or 6,6'-bond formation to give dioxapyrene or dihydrophenanthrene derivatives, respectively, with vivid changes in color (halochromism and electrochromism).

Cited by 6 publications

References 26 publications

N‐Substituted Acridinium as a Multi‐Responsive Recognition Unit in Supramolecular Chemistry

N‐Substituted Acridinium as a Multi‐Responsive Recognition Unit in Supramolecular Chemistry

Redox/pH Dual Stimuli‐Responsive Acridine Spiropyran

Conformational Switching through the One‐Electron Reduction of an Acridinium‐based, γ‐Cationic Phosphine Gold Complex

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