I. Ueber Dinitrophenylpyridiniumchlorid und dessen Umwandlungsproducte

Zincke, Th.

doi:10.1002/jlac.19043330212

Cited by 251 publications

(77 citation statements)

References 3 publications

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“…It is well known that N ‐(2,4‐dinitrophenyl)pyridinium chlorides, the so‐called Zincke salts, react with primary amines to yield N ‐substituted pyridinium compounds 41–49. Recently, we reported the synthesis of various Zincke salts, and some of them were used as starting materials for the synthesis of functional aromatic compounds and π‐conjugated polymers 50–58.…”

Section: Introductionmentioning

confidence: 99%

Reactive polythiophenes with zincke salt structure: Synthesis, polymer reactions, and chemical properties

Yamaguchi¹,

Nakahara²

2012

J. Polym. Sci. A Polym. Chem.

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Polythiophenes with reactive Zincke salt structure, such as PThThPy+DNP(Cl−)Th, were synthesized by the oxidation polymerization of 3′‐(4‐N‐(2,4‐dinitrophenyl)pyridinium chloride)‐2,2′:5′,2″‐terthiophene (ThThPy+DNP(Cl−)Th) with iron(III) chloride or copper(II) trifluoromethanesulfonate. The reaction of PThThPy+DNP(Cl−)Th with R‐NH2 (R = n‐hexyl (Hex) and phenyl (Ph)) substituted the 2,4‐dinitrophenyl group into the R group with the elimination of 2,4‐dinitroaniline to yield PThThPy+R(Cl−)Th. Similarly, model compounds, ThThPy+R(Cl−)Th (R = Hex and Ph), were also synthesized. In contrast to the photoluminescent ThThPyTh and PThThPyTh, the compounds PThThPy+DNP(Cl−)Th, PThThPy+R(Cl−)Th, and ThThPy+R(Cl−)Th showed no photoluminescence because their internal pyridinium rings acted as quenchers. Cyclic voltammetry measurements suggested that PThThPy+DNP(Cl−)Th received an electrochemical reduction of the pyridinium and 2,4‐dinitrophenyl groups and oxidation of the polymer backbone. PThThPy+DNP(Cl−)Th was electrically conductive (ρ = 2.0 × 10−6 S cm−1) in the non‐doped state. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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Section: Introductionmentioning

confidence: 99%

Reactive polythiophenes with zincke salt structure: Synthesis, polymer reactions, and chemical properties

Yamaguchi¹,

Nakahara²

2012

J. Polym. Sci. A Polym. Chem.

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“…[18] Synthetic yields were low,u naffected by the use of templatesa nd surprisingly sensitivet ow hether the intended alkyl linkers contained an odd or even number of carbon atoms. An alternative synthetic approachu sing the Zincke reaction [19,20] was designed according to the assumption that the use of an electron-rich template would be most efficient if applied to the cyclization of at etracationic bis-viologenc lip (5 4 + )r ather than to ap artially quaternized bipyridine intermediate such as 4 2 + (Scheme 1). An alternative synthetic approachu sing the Zincke reaction [19,20] was designed according to the assumption that the use of an electron-rich template would be most efficient if applied to the cyclization of at etracationic bis-viologenc lip (5 4 + )r ather than to ap artially quaternized bipyridine intermediate such as 4 2 + (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Flexible Viologen Cyclophanes: Odd/Even Effects on Intramolecular Interactions

et al. 2017

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The ability of three bis-viologen cyclophanes to act as redox-triggered contractile switches is investigated. Odd/even effects in the formation of cyclic bis-viologens are circumvented by the use of a Zincke salt intermediate and a tetrathiafulvalene template to prepare a flexible cyclophane with hexyl linkers. Comparative spectro-electrochemical studies of this macrocycle with two other pentyl- or heptyl-linked cyclic bis-viologens show that the development of intramolecular interactions in aqueous solution depends on the length of the bridges. This dependence is confirmed by EPR and DFT studies of the magnetic coupling in the diradical dication species. The anti-ferromagnetic or ferromagnetic nature of the coupling depend, respectively, on the odd or even number of methylene groups in the spacer.

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“…Salt(Cl), salt(FeCl 4 ), salt(N(CN) 2 ), and LPEI were prepared according to the literatures. The M n and M w values of LPEI determined by GPC were 20 380 and 25 660, respectively.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and chemical properties of polyethyleneimines crosslinked by penta‐2,4‐dienylideneammonium unit

Yamaguchi

Matsumoto

Miyoshi

et al. 2019

J of Applied Polymer Sci

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The reaction of N‐(2,4‐dinitrophenyl)pyridinium anion (salt(A); A = Cl−, FeCl4−, and (CN)2N−) with linear polyethyleneimine (LPEI; Mn = 20 380) and branched polyethyleneimines (BPEI1; Mn = 600, BPEI2; Mn = 10 000) at various molar feed ratios without using a catalyst resulted in pyridinium ring opening to yield ionic LPEI and BPEIs that were crosslinked by conjugated penta‐2,4‐dienylideneammonium (PDA) units, LPEI‐PDA, BPEI1‐PDA, and BPEI2‐PDA, respectively. A model compound was synthesized by the reaction of salt(Cl) with diethylamine. The solubilities of BPEI1‐PDA and BPEI2‐PDA depended on the feed ratios between salt(Cl) and BPEI1 or BPEI2. Dipping LPEI‐PDA into water and methanol yielded hydro‐ and organogels, respectively. UV–vis and reflection measurements revealed an expanded π‐conjugation length between the polymer chains due to the through‐space orbital interaction of the electrons on the two nitrogen atoms at the crosslinked positions in LPEI‐PDA, BPEI1‐PDA, and BPEI2‐PDA. Cyclic voltammetry analysis suggested that the polymers underwent electrochemical oxidation. Measurement using a superconducting quantum interference device (SQUID) indicated that LPEI‐PDA having FeCl4− anions was paramagnetic. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020, 137, 48712.

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I. Ueber Dinitrophenylpyridiniumchlorid und dessen Umwandlungsproducte

Cited by 251 publications

References 3 publications

Reactive polythiophenes with zincke salt structure: Synthesis, polymer reactions, and chemical properties

Reactive polythiophenes with zincke salt structure: Synthesis, polymer reactions, and chemical properties

Flexible Viologen Cyclophanes: Odd/Even Effects on Intramolecular Interactions

Synthesis and chemical properties of polyethyleneimines crosslinked by penta‐2,4‐dienylideneammonium unit

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