Synthesis and anion binding properties of 2,5-diamidothiophene polypyrrole Schiff base macrocycles

J. L. Sessler; V Roznyatovskiy; G. D. Pantos; NE Borisova; MD Reshetova; V. M. Lynch; V. N. Khrustalev; Y. A. Ustynyuk

doi:10.1021/ol052162b

Synthesis and anion binding properties of 2,5-diamidothiophene polypyrrole Schiff base macrocycles

J. L. Sessler, V Roznyatovskiy, G. D. Pantos, NE Borisova, MD Reshetova, V. M. Lynch, V. N. Khrustalev, Y. A. Ustynyuk

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Abstract

Two easy-to-synthesize polypyrrolic 2,5-diamidothiophene Schiff base macrocycles are reported, along with their anion binding properties as determined via UV-vis spectroscopic titrations carried out in dichloroethane. There is a striking difference between the interactions with anions of the two macrocycles, a finding ascribed to differences in their rigidity. For example, the more flexible dipyrromethane-derived macrocycle displays a 1.2:1 hydrogen sulfate versus nitrate selectivity, while its more rigid bipyrrole-derived congener shows a 7.4:1 selectivity in favor to hydrogen sulfate.

Original language	English
Pages (from-to)	5277-5280
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	23
DOIs	https://doi.org/10.1021/ol052162b
Publication status	Published - 10 Nov 2005

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title = "Synthesis and anion binding properties of 2,5-diamidothiophene polypyrrole Schiff base macrocycles",

abstract = "Two easy-to-synthesize polypyrrolic 2,5-diamidothiophene Schiff base macrocycles are reported, along with their anion binding properties as determined via UV-vis spectroscopic titrations carried out in dichloroethane. There is a striking difference between the interactions with anions of the two macrocycles, a finding ascribed to differences in their rigidity. For example, the more flexible dipyrromethane-derived macrocycle displays a 1.2:1 hydrogen sulfate versus nitrate selectivity, while its more rigid bipyrrole-derived congener shows a 7.4:1 selectivity in favor to hydrogen sulfate.",

author = "Sessler, \{J. L.\} and V Roznyatovskiy and Pantos, \{G. D.\} and NE Borisova and MD Reshetova and Lynch, \{V. M.\} and Khrustalev, \{V. N.\} and Ustynyuk, \{Y. A.\}",

year = "2005",

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doi = "10.1021/ol052162b",

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T1 - Synthesis and anion binding properties of 2,5-diamidothiophene polypyrrole Schiff base macrocycles

AU - Sessler, J. L.

AU - Roznyatovskiy, V

AU - Pantos, G. D.

AU - Borisova, NE

AU - Reshetova, MD

AU - Lynch, V. M.

AU - Khrustalev, V. N.

AU - Ustynyuk, Y. A.

PY - 2005/11/10

Y1 - 2005/11/10

N2 - Two easy-to-synthesize polypyrrolic 2,5-diamidothiophene Schiff base macrocycles are reported, along with their anion binding properties as determined via UV-vis spectroscopic titrations carried out in dichloroethane. There is a striking difference between the interactions with anions of the two macrocycles, a finding ascribed to differences in their rigidity. For example, the more flexible dipyrromethane-derived macrocycle displays a 1.2:1 hydrogen sulfate versus nitrate selectivity, while its more rigid bipyrrole-derived congener shows a 7.4:1 selectivity in favor to hydrogen sulfate.

AB - Two easy-to-synthesize polypyrrolic 2,5-diamidothiophene Schiff base macrocycles are reported, along with their anion binding properties as determined via UV-vis spectroscopic titrations carried out in dichloroethane. There is a striking difference between the interactions with anions of the two macrocycles, a finding ascribed to differences in their rigidity. For example, the more flexible dipyrromethane-derived macrocycle displays a 1.2:1 hydrogen sulfate versus nitrate selectivity, while its more rigid bipyrrole-derived congener shows a 7.4:1 selectivity in favor to hydrogen sulfate.

UR - https://www.scopus.com/pages/publications/28244447489

U2 - 10.1021/ol052162b

DO - 10.1021/ol052162b

M3 - Article

SN - 1523-7060

VL - 7

SP - 5277

EP - 5280

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Synthesis and anion binding properties of 2,5-diamidothiophene polypyrrole Schiff base macrocycles

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