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Title: Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride

Abstract

A microcrystalline carboxyl-functionalized imidazolium chloride, namely 1-carboxymethyl-3-ethylimidazolium chloride, C 7H 11N 2O 2 +·Cl , has been synthesized and characterized by elemental analysis, attenuated total reflectance Fourier transform IR spectroscopy (ATR-FT-IR), single-crystal X-ray diffraction, thermal analysis (TGA/DSC), and photoluminescence spectroscopy. In the crystal structure, cations and anions are linked by C—H...Cl and C—H...O hydrogen bonds to create a helix along the [010] direction. Adjacent helical chains are further interconnected through O—H...Cl and C—H...O hydrogen bonds to form a (101¯) layer. Finally, neighboring layers are joined together via C—H...Cl contacts to generate a three-dimensional supramolecular architecture. Thermal analyses reveal that the compound melts at 449.7 K and is stable up to 560.0 K under a dynamic air atmosphere. Photoluminescence measurements show that the compound exhibits a blue fluorescence and a green phosphorescence associated with spin-allowed ( 1π← 1π*) and spin-forbidden ( 1π← 3π*) transitions, respectively. As a result, the average luminescence lifetime was determined to be 1.40 ns for the short-lived ( 1π← 1π*) transition and 105 ms for the long-lived ( 1π← 3π*) transition.

Authors:
ORCiD logo [1]; ORCiD logo [2];  [3]
  1. Ames Lab., Ames, IA (United States)
  2. Ames Lab., Ames, IA (United States); Iowa State Univ., Ames, IA (United States); Stockholm Univ., Stockholm (Sweden); Wroclaw Research Centre EIT+, Wroclaw (Poland)
  3. Ames Lab., Ames, IA (United States); Iowa State Univ., Ames, IA (United States); Stockholm Univ., Stockholm (Sweden)
Publication Date:
Research Org.:
Ames Laboratory (AMES), Ames, IA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1455215
Report Number(s):
IS-J-9692
Journal ID: ISSN 2053-2296; ACSCGG; PII: S2053229618005272
Grant/Contract Number:  
AC02-07CH11358
Resource Type:
Accepted Manuscript
Journal Name:
Acta Crystallographica. Section C, Structural Chemistry (Online)
Additional Journal Information:
Journal Name: Acta Crystallographica. Section C, Structural Chemistry (Online); Journal Volume: 74; Journal Issue: 6; Journal ID: ISSN 2053-2296
Publisher:
International Union of Crystallography
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; carboxyl-functionalized imidazolium salt; hydrogen-bonding inter­action; thermal analysis; photoluminescence spectroscopy; crystal structure; ionic liquids

Citation Formats

Prodius, Denis, Wilk-Kozubek, Magdalena, and Mudring, Anja -Verena. Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride. United States: N. p., 2018. Web. doi:10.1107/S2053229618005272.
Prodius, Denis, Wilk-Kozubek, Magdalena, & Mudring, Anja -Verena. Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride. United States. doi:10.1107/S2053229618005272.
Prodius, Denis, Wilk-Kozubek, Magdalena, and Mudring, Anja -Verena. Tue . "Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride". United States. doi:10.1107/S2053229618005272. https://www.osti.gov/servlets/purl/1455215.
@article{osti_1455215,
title = {Synthesis, structural characterization and luminescence properties of 1-carboxymethyl-3-ethylimidazolium chloride},
author = {Prodius, Denis and Wilk-Kozubek, Magdalena and Mudring, Anja -Verena},
abstractNote = {A microcrystalline carboxyl-functionalized imidazolium chloride, namely 1-carboxymethyl-3-ethylimidazolium chloride, C7H11N2O2+·Cl–, has been synthesized and characterized by elemental analysis, attenuated total reflectance Fourier transform IR spectroscopy (ATR-FT-IR), single-crystal X-ray diffraction, thermal analysis (TGA/DSC), and photoluminescence spectroscopy. In the crystal structure, cations and anions are linked by C—H...Cl and C—H...O hydrogen bonds to create a helix along the [010] direction. Adjacent helical chains are further interconnected through O—H...Cl and C—H...O hydrogen bonds to form a (101¯) layer. Finally, neighboring layers are joined together via C—H...Cl contacts to generate a three-dimensional supramolecular architecture. Thermal analyses reveal that the compound melts at 449.7 K and is stable up to 560.0 K under a dynamic air atmosphere. Photoluminescence measurements show that the compound exhibits a blue fluorescence and a green phosphorescence associated with spin-allowed (1π←1π*) and spin-forbidden (1π←3π*) transitions, respectively. As a result, the average luminescence lifetime was determined to be 1.40 ns for the short-lived (1π←1π*) transition and 105 ms for the long-lived (1π←3π*) transition.},
doi = {10.1107/S2053229618005272},
journal = {Acta Crystallographica. Section C, Structural Chemistry (Online)},
number = 6,
volume = 74,
place = {United States},
year = {2018},
month = {5}
}

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    Works referencing / citing this record:

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    • Angewandte Chemie International Edition, Vol. 43, Issue 38, p. 4988-4992
    • DOI: 10.1002/anie.200460091

    The “Noncoordinating” Anion Tf2N− Coordinates to Yb2+: A Structurally Characterized Tf2N− Complex from the Ionic Liquid [mppyr][Tf2N]
    journal, August 2005

    • Mudring, Anja-Verena; Babai, Arash; Arenz, Sven
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    • DOI: 10.1002/anie.200501297

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    • Tang, Sifu; Babai, Arash; Mudring, Anja-Verena
    • Angewandte Chemie International Edition, Vol. 47, Issue 40
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    • Eike T. Spielberg, ; Edengeiser, Eugen; Mallick, Bert
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    • DOI: 10.1021/ic801213z

    Task-Specific Ionic Liquid for Solubilizing Metal Oxides
    journal, October 2006

    • Nockemann, Peter; Thijs, Ben; Pittois, Stijn
    • The Journal of Physical Chemistry B, Vol. 110, Issue 42
    • DOI: 10.1021/jp0642995

    The first homoleptic bis(trifluoromethanesulfonyl)amide complex compounds of trivalent f-elements
    journal, January 2006

    • Babai, Arash; Mudring, Anja-Verena
    • Dalton Transactions, Issue 15
    • DOI: 10.1039/b517694h

    Carboxylic acid functionalized imidazolium salts: sequential formation of ionic, zwitterionic, acid-zwitterionic and lithium salt-zwitterionic liquid crystals
    journal, January 2011

    • Lin, Joseph C. Y.; Huang, Chao-June; Lee, Yi-Ting
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    Catalytic “triangles”: binding of iron in task-specific ionic liquids
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    • Prodius, Denis; Macaev, Fliur; Stingaci, Eugenia
    • Chemical Communications, Vol. 49, Issue 19
    • DOI: 10.1039/c2cc36741f

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    • Prodius, Denis; Macaev, Fliur; Lan, Yanhua
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    • DOI: 10.1039/c3cc45554h

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