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

Research output: Contribution to journalArticle

35 Citations (Scopus)

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 languageEnglish
Pages (from-to)5277-5280
Number of pages4
JournalOrganic Letters
Volume7
Issue number23
DOIs
Publication statusPublished - 10 Nov 2005

Fingerprint

Schiff Bases
polypyrroles
imines
Sulfates
Anions
Hydrogen
sulfates
selectivity
Ethylene Dichlorides
anions
congeners
hydrogen
synthesis
Titration
rigidity
Rigidity
titration
Nitrates
nitrates
interactions

Cite this

Sessler, J. L., Roznyatovskiy, V., Pantos, G. D., Borisova, NE., Reshetova, MD., Lynch, V. M., ... Ustynyuk, Y. A. (2005). Synthesis and anion binding properties of 2,5-diamidothiophene polypyrrole Schiff base macrocycles. Organic Letters, 7(23), 5277-5280. https://doi.org/10.1021/ol052162b

Synthesis and anion binding properties of 2,5-diamidothiophene polypyrrole Schiff base macrocycles. / Sessler, J. L.; Roznyatovskiy, V; Pantos, G. D.; Borisova, NE; Reshetova, MD; Lynch, V. M.; Khrustalev, V. N.; Ustynyuk, Y. A.

In: Organic Letters, Vol. 7, No. 23, 10.11.2005, p. 5277-5280.

Research output: Contribution to journalArticle

Sessler, JL, Roznyatovskiy, V, Pantos, GD, Borisova, NE, Reshetova, MD, Lynch, VM, Khrustalev, VN & Ustynyuk, YA 2005, 'Synthesis and anion binding properties of 2,5-diamidothiophene polypyrrole Schiff base macrocycles', Organic Letters, vol. 7, no. 23, pp. 5277-5280. https://doi.org/10.1021/ol052162b
Sessler JL, Roznyatovskiy V, Pantos GD, Borisova NE, Reshetova MD, Lynch VM et al. Synthesis and anion binding properties of 2,5-diamidothiophene polypyrrole Schiff base macrocycles. Organic Letters. 2005 Nov 10;7(23):5277-5280. https://doi.org/10.1021/ol052162b
Sessler, J. L. ; Roznyatovskiy, V ; Pantos, G. D. ; Borisova, NE ; Reshetova, MD ; Lynch, V. M. ; Khrustalev, V. N. ; Ustynyuk, Y. A. / Synthesis and anion binding properties of 2,5-diamidothiophene polypyrrole Schiff base macrocycles. In: Organic Letters. 2005 ; Vol. 7, No. 23. pp. 5277-5280.
@article{f752e9bfce334b409702bd3e4f289ffa,
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",
month = "11",
day = "10",
doi = "10.1021/ol052162b",
language = "English",
volume = "7",
pages = "5277--5280",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "23",

}

TY - JOUR

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.

U2 - 10.1021/ol052162b

DO - 10.1021/ol052162b

M3 - Article

VL - 7

SP - 5277

EP - 5280

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 23

ER -