A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols

Silvia  Hristova; V Deneva; Michael  Pittelkow; Aurelien  Crochet; Fadhil S. Kamounah; Katharina M.  Fromm; Poul Erik Hansen; Liudmil  Antonov

doi:10.1016/j.dyepig.2018.03.070

A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols

Silvia Hristova, V Deneva, Michael Pittelkow, Aurelien Crochet, Fadhil S. Kamounah, Katharina M. Fromm, Poul Erik Hansen, Liudmil Antonov

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

Abstract

A series of aryl azo derivatives of naphthols (1–3) were studied by means of UV–Vis and NMR spectroscopy in different solvents as well as by quantum chemical calculations and X-ray analysis. Previous studies have shown that Sudan I (1) exists as a tautomeric mixture. The effect of the solvents is minimized by the existing intramolecular hydrogen bond. Therefore, the influence on the tautomeric state in structurally modified 1 has been investigated. Structure 2 contains an additional OH-group, which deprotonates easily and affects the position of the tautomeric equilibrium by changing the electronic properties of the substituent. The implementation of a sidearm in 3 creates a condition for competition between the nitrogen from the azo group and from the piperidine unit for the tautomeric proton. In this case the use of acid as a stimulus for controlling the tautomeric process was achieved.

Originalsprog	Engelsk
Tidsskrift	Dyes and Pigments
Vol/bind	156
Udgave nummer	September
Sider (fra-til)	91-99
Antal sider	9
ISSN	0143-7208
DOI	https://doi.org/10.1016/j.dyepig.2018.03.070
Status	Udgivet - 1 mar. 2018

Link til dokument

10.1016/j.dyepig.2018.03.070

A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-OLSAccepteret manuskript, 0,99 MBLicens: CC BY-NC-ND

Citer dette

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title = "A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols",

abstract = "A series of aryl azo derivatives of naphthols (1–3) were studied by means of UV–Vis and NMR spectroscopy in different solvents as well as by quantum chemical calculations and X-ray analysis. Previous studies have shown that Sudan I (1) exists as a tautomeric mixture. The effect of the solvents is minimized by the existing intramolecular hydrogen bond. Therefore, the influence on the tautomeric state in structurally modified 1 has been investigated. Structure 2 contains an additional OH-group, which deprotonates easily and affects the position of the tautomeric equilibrium by changing the electronic properties of the substituent. The implementation of a sidearm in 3 creates a condition for competition between the nitrogen from the azo group and from the piperidine unit for the tautomeric proton. In this case the use of acid as a stimulus for controlling the tautomeric process was achieved.",

keywords = "Azo dyes, Molecular spectroscopy, Molecular switches, Tautomerism",

author = "Silvia Hristova and V Deneva and Michael Pittelkow and Aurelien Crochet and Kamounah, {Fadhil S.} and Fromm, {Katharina M.} and Hansen, {Poul Erik} and Liudmil Antonov",

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AU - Hristova, Silvia

AU - Deneva, V

AU - Pittelkow, Michael

AU - Crochet, Aurelien

AU - Kamounah, Fadhil S.

AU - Fromm, Katharina M.

AU - Hansen, Poul Erik

AU - Antonov, Liudmil

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AB - A series of aryl azo derivatives of naphthols (1–3) were studied by means of UV–Vis and NMR spectroscopy in different solvents as well as by quantum chemical calculations and X-ray analysis. Previous studies have shown that Sudan I (1) exists as a tautomeric mixture. The effect of the solvents is minimized by the existing intramolecular hydrogen bond. Therefore, the influence on the tautomeric state in structurally modified 1 has been investigated. Structure 2 contains an additional OH-group, which deprotonates easily and affects the position of the tautomeric equilibrium by changing the electronic properties of the substituent. The implementation of a sidearm in 3 creates a condition for competition between the nitrogen from the azo group and from the piperidine unit for the tautomeric proton. In this case the use of acid as a stimulus for controlling the tautomeric process was achieved.

KW - Azo dyes

KW - Molecular spectroscopy

KW - Molecular switches

KW - Tautomerism

U2 - 10.1016/j.dyepig.2018.03.070

DO - 10.1016/j.dyepig.2018.03.070

M3 - Journal article

SN - 0143-7208

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EP - 99

JO - Dyes and Pigments

JF - Dyes and Pigments

IS - September

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